cdxml-toolkit 0.5.0__py3-none-any.whl

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Files changed (91) hide show
  1. cdxml_toolkit/__init__.py +18 -0
  2. cdxml_toolkit/_jre/__init__.py +2 -0
  3. cdxml_toolkit/_jre/temurin-21-jre-win-x64.zip +0 -0
  4. cdxml_toolkit/analysis/__init__.py +35 -0
  5. cdxml_toolkit/analysis/deterministic/__init__.py +12 -0
  6. cdxml_toolkit/analysis/deterministic/discover_experiment_files.py +413 -0
  7. cdxml_toolkit/analysis/deterministic/lab_book_formatter.py +701 -0
  8. cdxml_toolkit/analysis/deterministic/lcms_file_categorizer.py +928 -0
  9. cdxml_toolkit/analysis/deterministic/lcms_identifier.py +598 -0
  10. cdxml_toolkit/analysis/deterministic/mass_resolver.py +654 -0
  11. cdxml_toolkit/analysis/deterministic/multi_lcms_analyzer.py +1412 -0
  12. cdxml_toolkit/analysis/deterministic/procedure_writer.py +446 -0
  13. cdxml_toolkit/analysis/extract_nmr.py +47 -0
  14. cdxml_toolkit/analysis/format_procedure_entry.py +479 -0
  15. cdxml_toolkit/analysis/lcms_analyzer.py +1299 -0
  16. cdxml_toolkit/analysis/parse_analysis_file.py +134 -0
  17. cdxml_toolkit/cdxml_builder.py +920 -0
  18. cdxml_toolkit/cdxml_utils.py +342 -0
  19. cdxml_toolkit/chemdraw/__init__.py +5 -0
  20. cdxml_toolkit/chemdraw/_chemscript_server.py +562 -0
  21. cdxml_toolkit/chemdraw/cdx_converter.py +527 -0
  22. cdxml_toolkit/chemdraw/cdxml_to_image.py +262 -0
  23. cdxml_toolkit/chemdraw/cdxml_to_image_rdkit.py +296 -0
  24. cdxml_toolkit/chemdraw/chemscript_bridge.py +901 -0
  25. cdxml_toolkit/constants.py +304 -0
  26. cdxml_toolkit/coord_normalizer.py +438 -0
  27. cdxml_toolkit/deterministic_pipeline/__init__.py +6 -0
  28. cdxml_toolkit/deterministic_pipeline/legacy/__init__.py +5 -0
  29. cdxml_toolkit/deterministic_pipeline/legacy/eln_cdx_cleanup.py +509 -0
  30. cdxml_toolkit/deterministic_pipeline/legacy/eln_enrichment.py +1394 -0
  31. cdxml_toolkit/deterministic_pipeline/legacy/scheme_aligner.py +428 -0
  32. cdxml_toolkit/deterministic_pipeline/legacy/scheme_polisher.py +1337 -0
  33. cdxml_toolkit/deterministic_pipeline/legacy/scheme_polisher_v2.py +1340 -0
  34. cdxml_toolkit/deterministic_pipeline/scheme_reader_audit.py +931 -0
  35. cdxml_toolkit/deterministic_pipeline/scheme_reader_verify.py +1160 -0
  36. cdxml_toolkit/image/__init__.py +15 -0
  37. cdxml_toolkit/image/reaction_from_image.py +2103 -0
  38. cdxml_toolkit/image/structure_from_image.py +1711 -0
  39. cdxml_toolkit/layout/__init__.py +5 -0
  40. cdxml_toolkit/layout/alignment.py +1642 -0
  41. cdxml_toolkit/layout/reaction_cleanup.py +1002 -0
  42. cdxml_toolkit/layout/scheme_merger.py +2260 -0
  43. cdxml_toolkit/mcp_server/__init__.py +0 -0
  44. cdxml_toolkit/mcp_server/__main__.py +5 -0
  45. cdxml_toolkit/mcp_server/server.py +1567 -0
  46. cdxml_toolkit/naming/__init__.py +6 -0
  47. cdxml_toolkit/naming/aligned_namer.py +2342 -0
  48. cdxml_toolkit/naming/mol_builder.py +3722 -0
  49. cdxml_toolkit/naming/name_decomposer.py +2843 -0
  50. cdxml_toolkit/naming/reactions_datamol.json +2414 -0
  51. cdxml_toolkit/office/__init__.py +5 -0
  52. cdxml_toolkit/office/doc_from_template.py +722 -0
  53. cdxml_toolkit/office/ole_embedder.py +808 -0
  54. cdxml_toolkit/office/ole_extractor.py +272 -0
  55. cdxml_toolkit/perception/__init__.py +10 -0
  56. cdxml_toolkit/perception/compound_search.py +229 -0
  57. cdxml_toolkit/perception/eln_csv_parser.py +240 -0
  58. cdxml_toolkit/perception/rdf_parser.py +664 -0
  59. cdxml_toolkit/perception/reactant_heuristic.py +1045 -0
  60. cdxml_toolkit/perception/reaction_parser.py +2150 -0
  61. cdxml_toolkit/perception/scheme_reader.py +2948 -0
  62. cdxml_toolkit/perception/scheme_refine.py +1404 -0
  63. cdxml_toolkit/perception/scheme_segmenter.py +619 -0
  64. cdxml_toolkit/perception/spatial_assignment.py +1013 -0
  65. cdxml_toolkit/rdkit_utils.py +605 -0
  66. cdxml_toolkit/render/__init__.py +17 -0
  67. cdxml_toolkit/render/auto_layout.py +229 -0
  68. cdxml_toolkit/render/compact_parser.py +632 -0
  69. cdxml_toolkit/render/parser.py +706 -0
  70. cdxml_toolkit/render/render_scheme.py +267 -0
  71. cdxml_toolkit/render/renderer.py +2387 -0
  72. cdxml_toolkit/render/schema.py +90 -0
  73. cdxml_toolkit/render/scheme_maker.py +1043 -0
  74. cdxml_toolkit/render/scheme_yaml_writer.py +1487 -0
  75. cdxml_toolkit/resolve/__init__.py +13 -0
  76. cdxml_toolkit/resolve/cas_resolver.py +430 -0
  77. cdxml_toolkit/resolve/chemscanner_abbreviations.json +28813 -0
  78. cdxml_toolkit/resolve/condensed_formula.py +493 -0
  79. cdxml_toolkit/resolve/jre_manager.py +195 -0
  80. cdxml_toolkit/resolve/reagent_abbreviations.json +1046 -0
  81. cdxml_toolkit/resolve/reagent_db.py +285 -0
  82. cdxml_toolkit/resolve/superatom_data.json +2856 -0
  83. cdxml_toolkit/resolve/superatom_table.py +146 -0
  84. cdxml_toolkit/text_formatting.py +298 -0
  85. cdxml_toolkit-0.5.0.dist-info/METADATA +318 -0
  86. cdxml_toolkit-0.5.0.dist-info/RECORD +91 -0
  87. cdxml_toolkit-0.5.0.dist-info/WHEEL +5 -0
  88. cdxml_toolkit-0.5.0.dist-info/entry_points.txt +17 -0
  89. cdxml_toolkit-0.5.0.dist-info/licenses/LICENSE +21 -0
  90. cdxml_toolkit-0.5.0.dist-info/licenses/NOTICE.md +37 -0
  91. cdxml_toolkit-0.5.0.dist-info/top_level.txt +1 -0
cdxml_toolkit/naming/reactions_datamol.json ADDED
@@ -0,0 +1,2414 @@
1
+ {
2
+ "123-triazole-1": {
3
+ "description": "Copper-catalyzed Huisgen cycloaddition of an alkyne and an azide to form a 123-triazole (implicit azide formation from primary and secondary halides).",
4
+ "ld_data": {
5
+ "display_smarts": "[#6:101]-[#6]#[#6].[#6:102]-[#7]=[#7+]=[#7-]>>[#7]1-[#6](-[#6:101])=[#6]-[#7](-[#6:102])-[#7]=1"
6
+ },
7
+ "long_name": "Huisgen Cycloaddition (1,4 regio)",
8
+ "retro_smarts": "[#6;!$(C(-C)(-C)-C);!$(C=[C,N,O,S]):3]-[#7]1:[#6;H1:1]:[#6:2](-!@[#6:4]):[#7]:[#7]:1>>[#6:4]-[#6:2]#[#6:1].[#6:3]-Br",
9
+ "rhs_classes": [
10
+ "alkynes-monosub",
11
+ "halides-primsec"
12
+ ],
13
+ "syn_smarts": "[#6:101]-[#6:1]#[#6;H1:2].[#6;!$(C(-C)(-C)-C);!$(C=[C,N,O,S]):102]-[Cl,Br,I,N&$([N]=[N+]=[N-])]>>[#6:102]-[#7]1-[#6:2]=[#6:1](-[#6:101])-[#7]=[#7]-1",
14
+ "tags": [
15
+ "heterocycle formation",
16
+ "triazole",
17
+ "click",
18
+ "cyclization"
19
+ ],
20
+ "tier": 1
21
+ },
22
+ "123-triazole-2": {
23
+ "description": "Copper-catalyzed Huisgen cycloaddition of an alkyne and an azide to form a 123-triazole.",
24
+ "ld_data": {
25
+ "display_smarts": "[#6:101]-[#6]#[#6].[#6:102]-[#7]=[#7+]=[#7-]>>[#7]1-[#6](-[#6:101])=[#6]-[#7](-[#6:102])-[#7]=1"
26
+ },
27
+ "long_name": "Huisgen Cycloaddition (1,4 regio)",
28
+ "retro_smarts": "[#6;!$(C(-C)(-C)-C);!$(C=[C,N,O,S]):3]-[#7:5]1:[#6;H1:1]:[#6:2](-!@[#6:4]):[#7:7]:[#7:6]:1>>[#6:4]-[#6:2]#[#6:1].[#6:3]-[N:5]=[N+:6]=[N-:7]",
29
+ "rhs_classes": [
30
+ "alkynes-monosub",
31
+ "azides"
32
+ ],
33
+ "syn_smarts": "[#6:101]-[#6:1]#[#6;H1:2].[#6;!$(C(-C)(-C)-C);!$(C=[C,N,O,S]):102]-[N&$([N]=[N+]=[N-])]>>[#6:102]-[#7]1-[#6:2]=[#6:1](-[#6:101])-[#7]=[#7]-1",
34
+ "tags": [
35
+ "heterocycle formation",
36
+ "triazole",
37
+ "click",
38
+ "cyclization"
39
+ ],
40
+ "tier": 1
41
+ },
42
+ "123-triazole-3": {
43
+ "description": "Ruthenium-catalyzed Huisgen cycloaddition of an alkyne and an azide to form a 123-triazole (implicit azide formation from primary and secondary halides).",
44
+ "ld_data": {
45
+ "display_smarts": "[#6:101]-[#6]#[#6].[#6:102]-[#7]=[#7+]=[#7-]>>[#7]1-[#6]=[#6](-[#6:101])-[#7](-[#6:102])-[#7]=1"
46
+ },
47
+ "long_name": "Huisgen Cycloaddition (1,5 regio)",
48
+ "retro_smarts": "[#6;!$(C(-C)(-C)-C);!$(C=[C,N,O,S]):3]-[#7]1:[#6:2](-!@[#6:4]):[#6;H1:1]:[#7]:[#7]:1>>[#6:4]-[#6:2]#[#6:1].[#6:3]-Br",
49
+ "rhs_classes": [
50
+ "alkynes-monosub",
51
+ "halides-primsec"
52
+ ],
53
+ "syn_smarts": "[#6:101]-[#6:1]#[#6;H1:2].[#6;!$(C(-C)(-C)-C);!$(C=[C,N,O,S]):102]-[Cl,Br,I,N&$([N]=[N+]=[N-])]>>[#6:102]-[#7]1-[#6:1](-[#6:101])=[#6:2]-[#7]=[#7]-1",
54
+ "tags": [
55
+ "heterocycle formation",
56
+ "triazole",
57
+ "click",
58
+ "cyclization"
59
+ ],
60
+ "tier": 1
61
+ },
62
+ "123-triazole-4": {
63
+ "description": "Ruthenium-catalyzed Huisgen cycloaddition of an alkyne and an azide to form a 123-triazole.",
64
+ "ld_data": {
65
+ "display_smarts": "[#6:101]-[#6]#[#6].[#6:102]-[#7]=[#7+]=[#7-]>>[#7]1-[#6]=[#6](-[#6:101])-[#7](-[#6:102])-[#7]=1"
66
+ },
67
+ "long_name": "Huisgen Cycloaddition (1,5 regio)",
68
+ "retro_smarts": "[#6;!$(C(-C)(-C)-C);!$(C=[C,N,O,S]):3]-[#7:5]1:[#6:2](-!@[#6:4]):[#6;H1:1]:[#7:7]:[#7:6]:1>>[#6:4]-[#6:2]#[#6:1].[#6:3]-[N:5]=[N+:6]=[N-:7]",
69
+ "rhs_classes": [
70
+ "alkynes-monosub",
71
+ "azides"
72
+ ],
73
+ "syn_smarts": "[#6:101]-[#6:1]#[#6;H1:2].[#6;!$(C(-C)(-C)-C);!$(C=[C,N,O,S]):102]-[N&$([N]=[N+]=[N-])]>>[#6:102]-[#7]1-[#6:1](-[#6:101])=[#6:2]-[#7]=[#7]-1",
74
+ "tags": [
75
+ "heterocycle formation",
76
+ "triazole",
77
+ "click",
78
+ "cyclization"
79
+ ],
80
+ "tier": 1
81
+ },
82
+ "124-triazole-1": {
83
+ "description": "124-triazole from an aryl nitrile and an amidine.",
84
+ "ld_data": {
85
+ "display_smarts": "[#6:201]-[#6]#[#7].[#6:101]-[#6](=[#7])-[#7]>>[#6:201]-[#6]1-[#7]=[#6](-[#6:101])-[#7]-[#7]=1"
86
+ },
87
+ "long_name": "3,5-Disubstituted 1,2,4-Triazole formation from aryl nitriles and amidines",
88
+ "retro_smarts": "[c:101]-[#6:1]1:[#7;D2:4]:[#6:5](-[#6;!$(C=[C,N,S,O]):102]):[#7;D2:3]:[#7;D2:2]:1>>[c:101]-[#6:1]#[#7:2].[#6;!$(C=[C,N,S,O]):102]-[#6:5](=[#7;H1:3])-[#7;H2:4]",
89
+ "rhs_classes": [
90
+ "nitriles-aryl",
91
+ "amidines"
92
+ ],
93
+ "syn_smarts": "[c:101]-[#6:1]#[#7:2].[#6;!$(C=[C,N,S,O]):102]-[#6:5](=[#7;H1:3])-[#7;H2:4]>>[c:101]-[#6:1]1-[#7;H0:4]=[#6:5](-[#6:102])-[#7;H1:3]-[#7:2]=1",
94
+ "tags": [
95
+ "heterocycle formation",
96
+ "triazole",
97
+ "cyclization"
98
+ ],
99
+ "tier": 1
100
+ },
101
+ "124-triazole-2": {
102
+ "description": "124-triazole from a nitrile and hydrazide.",
103
+ "ld_data": {
104
+ "display_smarts": "[#6:101]-[#6]#[#7].[#7]-[#7]-[#6](=O)-[#6:102]>>[#6](-[#6:101])1-[#7]=[#6](-[#6:102])-[#7]-[#7]=1"
105
+ },
106
+ "long_name": "3,5-Disubstituted 1,2,4-Triazole formation from hydrazides",
107
+ "retro_smarts": "[#6:1](-[#6:101])1:[#7;D2:2]:[#6:5](-[#6;!$(C=[C,N,S,O]):102]):[#7;D2:4]:[#7;D2:3]:1>>[#6:101]-[#6:1]#[#7:2].[#7;H2:3]-[#7;H1:4]-[#6:5](=O)-[#6:102]",
108
+ "rhs_classes": [
109
+ "nitriles",
110
+ "hydrazides"
111
+ ],
112
+ "syn_smarts": "[#6:101]-[#6:1]#[#7:2].[#7;H2:3]-[#7;H1:4]-[#6:5](=O)-[#6;!$(C=[C,N,S,O]):102]>>[#6:1](-[#6:101])1-[#7:2]=[#6:5](-[#6:102])-[#7;H1:4]-[#7;H0:3]=1",
113
+ "tags": [
114
+ "heterocycle formation",
115
+ "triazole",
116
+ "cyclization"
117
+ ],
118
+ "tier": 1
119
+ },
120
+ "124-triazole-3": {
121
+ "description": "124-triazole from a nitrile and a carboxylate using hydrazine.",
122
+ "ld_data": {
123
+ "display_smarts": "[#6:101]-[#6]#[#7].[#6:102]-[#6](=O)-O>>[#6](-[#6:101])1=[#7]-[#6](-[#6:102])=[#7]-[#7]-1"
124
+ },
125
+ "long_name": "3,5-Disubstituted 1,2,4-Triazole formation from carboxylates",
126
+ "retro_smarts": "[#6:1](-[#6:101])1:[#7;D2:2]:[#6:5](-[#6;!$(C=[C,N,S,O]):102]):[#7;D2]:[#7;D2]:1>>[#6:101]-[#6:1]#[#7:2].[#6:102]-[#6:5](=O)-[O;H1]",
127
+ "rhs_classes": [
128
+ "nitriles",
129
+ "carboxylates"
130
+ ],
131
+ "syn_smarts": "[#6:101]-[#6:1]#[#7:2].[#6;!$(C=[C,N,O,S]):102]-[C:3](=O)-[O;H1]>>[#6:1](-[#6:101])1=[#7:2]-[#6:3](-[#6:102])=[#7]-[#7]-1",
132
+ "tags": [
133
+ "heterocycle formation",
134
+ "triazole",
135
+ "cyclization"
136
+ ],
137
+ "tier": 1
138
+ },
139
+ "5-het-amination": {
140
+ "description": "Amination of 5-member heterocycles (n-alkyl-imidazole, thiazole, oxazole, isoxazole, benzothiazole, benzimidazole, and benzoxazole).",
141
+ "ld_data": {
142
+ "display_smarts": "[#35]-C1=N-C2-C=C-C=C-C=2-N(-[#6])-1.[#7]-[#6:101]>>[#6:101]-[#7]-C1=N-C2-C=C-C=C-C=2-N(-[#6])-1"
143
+ },
144
+ "long_name": "Amination of 5-member heterocycles (n-alkyl-imidazole, thiazole, oxazole, isoxazole, benzothiazole, benzimidazole, and benzoxazole)",
145
+ "retro_smarts": "[c;r5;$(c1n(-[#6])ccn1),$(c1sccn1),$(c1occn1),$(c1sc2ccccc2n1),$(c1n(-[#6])c2ccccc2n1),$(c1[n;H1]c2ccccc2n1),$(c1oc2ccccc2n1),$(c1ccon1),$(c1c2ccccc2on1):1]-!@[N;$([N;H0](-[#6;!$(C=[C,N,O,S])])(-[c:1])-[#6;!$(C=[C,N,O,S])]),$([N;H1](-[c:1])-[#6;!$(C=[C,N,O,S])]);!$(N-[C,N,O,S]=[C,N,O,S]);!$(N~[N,O,S]):2]>>[c:1]-[#17].[#7:2]",
146
+ "rhs_classes": [
147
+ "halides-5het",
148
+ "amines-primsec"
149
+ ],
150
+ "syn_smarts": "[#17,#35]-[c;r5;$(c1n(-[#6])ccn1),$(c1sccn1),$(c1occn1),$(c1sc2ccccc2n1),$(c1n(-[#6])c2ccccc2n1),$(c1[n;H1]c2ccccc2n1),$(c1oc2ccccc2n1),$(c1ccon1),$(c1c2ccccc2on1):1].[N;$([N;H1](-[#6;!$(C=[C,N,O,S])])-[#6;!$(C=[C,N,O,S])]),$([N;H2]-[#6;!$(C=[C,N,O,S])]);!$(N-[C,N,O,S]=[C,N,O,S]);!$(N~[N,O,S]):2]>>[c:1]-[#7:2]",
151
+ "tags": [
152
+ "C-N bond formation",
153
+ "C-N",
154
+ "heterocycle",
155
+ "amination"
156
+ ],
157
+ "tier": 1
158
+ },
159
+ "5-het-arylation": {
160
+ "description": "Arylation of 5-member heterocycles, including: thiophene, n-methyl-imidazole, 4-methyl-thiazole, 2-methyl-furan, benzothiophene, and benzothiazole.",
161
+ "ld_data": {
162
+ "display_smarts": "[H]-[#6]-1=[#6,#7]-[#6,#7]=C-[#7,#8,#16]-1.Br-[#6:201]>>[#6:201]-C-1=[#6,#7]-[#6,#7]=C-[#7,#8,#16]-1 |$;;;;;;;Aryl_p;Aryl_p;;;;;$|"
163
+ },
164
+ "long_name": "5-Member heterocycle arylation from aryl bromides",
165
+ "retro_smarts": "[c;r5;$(c1sc(-[#6])[c;H1][c;H1]1),$(c1s[c;H1][c;H1][c;H1]1),$(c1[n;H1][c;H1]n[c;H1]1),$(c1n(-[#6])[c;H1]n[c;H1]1),$(c1s[c;H1]nc(-[#6])1),$(c1oc(-[#6])[c;H1][c;H1]1),$(c1sc2ccccc2[c;H1]1),$(c1sc2ccccc2n1):1]-!@[c:2]>>[c;H1:1].[c:2]-Br",
166
+ "rhs_classes": [
167
+ "5het-H1",
168
+ "bromides-aryl"
169
+ ],
170
+ "syn_smarts": "[c;H1;r5;$(c1sc(-[#6])[c;H1][c;H1]1),$(c1s[c;H1][c;H1][c;H1]1),$(c1[n;H1][c;H1]n[c;H1]1),$(c1n(-[#6])[c;H1]n[c;H1]1),$(c1s[c;H1]nc(-[#6])1),$(c1oc(-[#6])[c;H1][c;H1]1),$(c1sc2ccccc2[c;H1]1),$(c1sc2ccccc2n1):1].[c:2]-Br>>[c:1]-[c:2]",
171
+ "tags": [
172
+ "C-C bond formation",
173
+ "C-C",
174
+ "heterocycle",
175
+ "arylation"
176
+ ],
177
+ "tier": 1
178
+ },
179
+ "BOC-deprotection": {
180
+ "description": "Deprotection of a Boc-protected amine",
181
+ "ld_data": {
182
+ "display_smarts": "[#6]-[#6](-[#6])(-[#6])-O-C(=O)-N-[#6:101]>>[#7]-[#6:101]"
183
+ },
184
+ "long_name": "Deprotection of a BOC-protected amine",
185
+ "retro_smarts": "[#6;!$([#6]=[C,N,O,S]):101]-[N;$([N;H1](-[#6;!$([#6]=[C,N,O,S]):101])-[#6;!$([#6]=[C,N,O,S]):103]),$([N;H2]-[#6;!$([#6]=[C,N,O,S]):101]):2]>>[#6:101]-[N;$([N;H1](-C=O)-[#6:101]),$([N;H0](-C=O)(-[#6:103])-[#6:101]):2]-C(=O)-O-C(-C)(-C)-C",
186
+ "syn_smarts": "[#6;!$([#6]=[#7,#8,#16]):101]-[N;$([N;H1](-C=O)-[#6;!$([#6]=[#6,#7,#8,#16]):101]),$([N;H0](-C=O)(-[#6;!$([#6]=[#6,#7,#8,#16]):103])-[#6;!$([#6]=[#6,#7,#8,#16]):101]):2]-!@C(=O)-O-C(-[C;H3])(-[C;H3])-[C;H3]>>[#6:101]-[N:2]",
187
+ "tags": [
188
+ "Boc",
189
+ "Boc-deprotection",
190
+ "protecting group",
191
+ "transformation"
192
+ ],
193
+ "tier": 1
194
+ },
195
+ "BOC-protection": {
196
+ "description": "Protection of a primary or secondary amine with a Boc-group",
197
+ "ld_data": {
198
+ "display_smarts": "[#7]-[#6:101]>>[#6]-[#6](-[#6])(-[#6])-O-C(=O)-N-[#6:101]"
199
+ },
200
+ "long_name": "Protection of a primary or secondary amine with a Boc-group",
201
+ "retro_smarts": "[#6;!$([#6]=[#7,#8,#16]):101]-[N;$([N;H1](-C=O)-[#6;!$([#6]=[#6,#7,#8,#16]):101]),$([N;H0](-C=O)(-[#6;!$([#6]=[#6,#7,#8,#16]):103])-[#6;!$([#6]=[#6,#7,#8,#16]):101]):2]-!@C(=O)-O-C(-[C;H3])(-[C;H3])-[C;H3]>>[#6:101]-[N:2]",
202
+ "rhs_classes": [
203
+ "amines-primsec"
204
+ ],
205
+ "syn_smarts": "[#6;!$([#6]=[C,N,O,S]):101]-[N;$([N;H1](-[#6;!$([#6]=[C,N,O,S]):101])-[#6;!$([#6]=[C,N,O,S]):103]),$([N;H2]-[#6;!$([#6]=[C,N,O,S]):101]):2]>>[#6:101]-[N;$([N;H1](-C=O)-[#6:101]),$([N;H0](-C=O)(-[#6:103])-[#6:101]):2]-C(=O)-O-C(-C)(-C)-C",
206
+ "tags": [
207
+ "Boc",
208
+ "Boc-protection",
209
+ "protecting group",
210
+ "transformation"
211
+ ],
212
+ "tier": 1
213
+ },
214
+ "N-azole-arylation": {
215
+ "description": "N-arylation of azoles, including: indole, pyrazole, imidazole, triazole, tetrazole, benzimidazole, and indazoles.",
216
+ "ld_data": {
217
+ "display_smarts": "[#8]-[#5](-[#8])-[#6:201].[H]-[#7]-1-[C,N]=[C,N]-C=[C,N]-1>>[#6:201]-N-1-[C,N]=[C,N]-C=[C,N]-1 |$;;;Aryl_p;;;;;;;Aryl_p;;;;;$|"
218
+ },
219
+ "long_name": "N-Arylation of azoles from boronic acids/esters",
220
+ "retro_smarts": "[c:1]-!@[n;$(n1nccc1),$(n1cccc1),$(n1cncc1),$(n1ncnc1),$(n1cnnc1),$(n1nccn1):2]>>[c:1]-B(-O)-O.[n;H1:2]",
221
+ "rhs_classes": [
222
+ "boronates-aryl",
223
+ "azoles-nH"
224
+ ],
225
+ "syn_smarts": "[c:1]-B(-O)-O.[n;$(n1nccc1),$(n1cccc1),$(n1cncc1),$(n1ncnc1),$(n1cnnc1),$(n1nccn1);D2;H1:2]>>[c:1]-[n;D3;H0:2]",
226
+ "tags": [
227
+ "azole",
228
+ "N-arylation"
229
+ ],
230
+ "tier": 1
231
+ },
232
+ "acylation-1": {
233
+ "description": "Acylation of an alkyne with an acid chloride.",
234
+ "ld_data": {
235
+ "display_smarts": "[#6:101]-[C]#[#6].[#6:102]-C(=O)-Cl>>[#6:102]-C(=O)-C#C-[#6:101]"
236
+ },
237
+ "long_name": "Ynone synthesis from alkynes and acid chlorides",
238
+ "retro_smarts": "[#6;!$([#6]=[#6,#7,#8,#16]):1]-[C:2]#[C:3]-!@[#6:4](=[O:5])-[#6;!$([#6]=[#6,#7,#8,#16]):6]>>[#6:1]-[C:2]#[C:3].[#6:6]-[#6:4](=[O:5])-Cl",
239
+ "rhs_classes": [
240
+ "alkynes-monosub",
241
+ "acid_chlorides"
242
+ ],
243
+ "syn_smarts": "[#6;!$([#6]=[#6,#7,#8,#16]):101]-[C:2]#[C;H1:3].[#6;!$([#6]=[#6,#7,#8,#16]):102]-[C:4](=O)-Cl>>[#6:101]-[C:2]#[C;H0:3]-[C:4](=O)-[#6:102]",
244
+ "tags": [
245
+ "acylation",
246
+ "alkyne"
247
+ ],
248
+ "tier": 1
249
+ },
250
+ "alkylation-1": {
251
+ "description": "Alkylation of a primary or secondary amine using a primary or secondary alkyl halide.",
252
+ "ld_data": {
253
+ "display_smarts": "[#6:101]-Br.[#6:102]-[#7]>>[#6:101]-N-[#6:102]"
254
+ },
255
+ "long_name": "Alkylation of amines using alkyl halides",
256
+ "retro_smarts": "[#6;!$([#6](-[#6])(-[#6])-[#6]);!$(C=[C,N,O,S]);!$(C#N);!$(c):1]-!@[#7;!$(N-C#N);$([N;H0](-[#6;!$([#6](-[#6])(-[#6])-[#6]);!$(C=[C,N,O,S]);!$(c):1])(-[#6;!$(C=[C,N,O,S]);$(c),$([#6;!H0]):3])-[#6;!$(C=[C,N,O,S]);$(c),$([#6;!H0])]),$([N;H1](-[#6;!$(C=[C,N,O,S]);$(c),$([#6;!H0]):3])-[#6;!$([#6](-[#6])(-[#6])-[#6]);!$(C=[C,N,O,S]);!$(c):1]):2]-[#6;!$(C=[C,N,O,S]);$(c),$([#6;!H0]):3]>>[#6:1]-Br.[#7:2]-[#6:3]",
257
+ "rhs_classes": [
258
+ "halides-primsec",
259
+ "amines-primsec"
260
+ ],
261
+ "syn_smarts": "[#6;!$([#6](-[#6])(-[#6])-[#6]);!$(C=[C,N,O,S]);!$(C#N);!$(c):101]-[Cl,Br,I].[#6;!$(C=[C,N,O,S]);$(c),$([#6;!H0]):102]-[#7;!$(N-C#N);$([N;H1](-[#6;!$(C=[C,N,O,S]);$(c),$([#6;!H0])])-[#6;!$(C=[C,N,O,S]);$(c),$([#6;!H0]):102]),$([N;H2]-[#6;!$(C=[C,N,O,S]);$(c),$([#6;!H0]):102]):2]>>[#6:101]-[#7:2]-[#6:102]",
262
+ "tags": [
263
+ "amine",
264
+ "alkylation",
265
+ "C-N bond formation",
266
+ "C-N"
267
+ ],
268
+ "tier": 1
269
+ },
270
+ "alkylation-2": {
271
+ "description": "N-Alkylation of heterocycles using a primary or secondary alkyl halide.",
272
+ "ld_data": {
273
+ "display_smarts": "[#6:101]-Br.[H]-N-1-C=C-C=C-1>>[#6:101]-N1-C=C-C=C-1"
274
+ },
275
+ "long_name": "N-Alkylation of heterocycles using alkyl halides",
276
+ "retro_smarts": "[#6;!$([#6](-[#6])(-[#6])-[#6]);!$(C=[C,N,O,S]);!$(C#N);!$(c):1]-!@[n;$(n1[c,n][c,n][c,n]c1),$(n1c(=O)[c,n][c,n][c,n][c,n]1),$(n1[c,n][c,n]c(=O)[c,n][c,n]1):2]>>[#6:1]-Br.[n;H1:2]",
277
+ "rhs_classes": [
278
+ "halides-primsec",
279
+ "heterocycles-NH"
280
+ ],
281
+ "syn_smarts": "[#6;!$([#6](-[#6])(-[#6])-[#6]);!$(C=[C,N,O,S]);!$(C#N);!$(c):101]-[Cl,Br,I].[n;$([n;H1]1[c,n][c,n][c,n]c1),$([n;H1]1c(=O)[c,n][c,n][c,n][c,n]1),$([n;H1]1[c,n][c,n]c(=O)[c,n][c,n]1):2]>>[#6:101]-[n;H0:2]",
282
+ "tags": [
283
+ "heterocycle",
284
+ "alkylation",
285
+ "C-N bond formation",
286
+ "C-N"
287
+ ],
288
+ "tier": 1
289
+ },
290
+ "amide_coupling-1": {
291
+ "description": "Traditional amide coupling using a carboxylic acid and a primary or secondary amine.",
292
+ "ld_data": {
293
+ "display_smarts": "[#6:101]-C(=O)-O.[#7]-[#6:102]>>[#6:102]-N-C(=O)-[#6:101]"
294
+ },
295
+ "long_name": "Amide synthesis from carboxylic acids and primary or secondary amines",
296
+ "retro_smarts": "[#6;!$(C=[C,N,O,S]):1]-[N;$([N;H0](-[#6;!$(C=[C,N,O,S]):1])-[#6;!$(C=[C,N,O,S])]),$([N;H1]);!$(N=*);!$([N-]);!$(N#*);!$([ND4]);!$(N[O,N]):2]-!@[C;!R:3](=[O:5])-[#6;!$(C=[C,N,O,S]):4]>>[#6:4]-[C:3](=[O:5])-[O;H1].[N:2]-[#6:1]",
297
+ "rhs_classes": [
298
+ "carboxylates",
299
+ "amines-primsec"
300
+ ],
301
+ "syn_smarts": "[#6;!$(C=[C,N,O,S]):101]-[C:2](=O)-[O;H1].[N;$([N;H1](-[#6;!$(C=[C,N,O,S])])-[#6;!$(C=[C,N,O,S])]),$([N;H2]-[#6;!$(C=[C,N,O,S])]);!$(N-[C,N,O,S]=[C,N,O,S]):3]-[#6;!$(C=[C,N,O,S]):102]>>[#6:101]-[C:2](=O)-[N:3]-[#6:102]",
302
+ "tags": [
303
+ "amide coupling",
304
+ "amide"
305
+ ],
306
+ "tier": 1
307
+ },
308
+ "amide_coupling-2": {
309
+ "description": "Schotten-Baumann: Amide coupling using an acid chloride and a primary or secondary amine.",
310
+ "ld_data": {
311
+ "display_smarts": "[#6:101]-C(=O)-Cl.[#7]-[#6:102]>>[#6:102]-N-C(=O)-[#6:101]"
312
+ },
313
+ "long_name": "Schotten-Baumann amide synthesis from acid chlorides and primary or secondary amines",
314
+ "retro_smarts": "[#6;!$(C=[C,N,O,S]):1]-[N;$([N;H0](-[#6;!$(C=[C,N,O,S]):1])-[#6;!$(C=[C,N,O,S])]),$([N;H1]);!$(N=*);!$([N-]);!$(N#*);!$([ND4]);!$(N[O,N]):2]-!@[C;!R:3](=[O:5])-[#6;!$(C=[C,N,O,S]):4]>>[#6:4]-[C:3](=[O:5])-Cl.[N:2]-[#6:1]",
315
+ "rhs_classes": [
316
+ "acid_chlorides",
317
+ "amines-primsec"
318
+ ],
319
+ "syn_smarts": "[#6;!$(C=[C,N,O,S]):101]-[C:2](=O)-Cl.[N;$([N;H1](-[#6;!$(C=[C,N,O,S])])-[#6;!$(C=[C,N,O,S])]),$([N;H2]-[#6;!$(C=[C,N,O,S])]);!$(N-[C,N,O,S]=[C,N,O,S]):3]-[#6;!$(C=[C,N,O,S]):102]>>[#6:101]-[C:2](=O)-[N:3]-[#6:102]",
320
+ "tags": [
321
+ "amide coupling",
322
+ "amide"
323
+ ],
324
+ "tier": 1
325
+ },
326
+ "amide_coupling-3": {
327
+ "description": "Intramolecular amide coupling",
328
+ "ld_data": {
329
+ "display_smarts": "[#7]-[#6]-[#6]-[#6]-[#6](-[#8])=[O]>>[O]=[#6]-1-[#6]-[#6]-[#6]-[#7]-1 |Sg:n:2::ht,Sg:n:10::ht|"
330
+ },
331
+ "long_name": "Intramolecular amide coupling to form lactams",
332
+ "retro_smarts": "[#6:3]@[#6:4]@[#6:5](=[#8:6])@[#7;$([#7;H0]([#6;$([#6]=O)])([#6])[#6;!$([#6]=[C,N,O,S]):2]),$([#7;H1]([#6;$([#6]=O)])[#6;!$([#6]=[C,N,O,S]):2]):1]@[#6;!$([#6]=[C,N,O,S]):2]>>([N:1][#6:2].[#6:3][#6:4][C:5](=[O:6])-[O;H1])",
333
+ "syn_smarts": "([N;$([N;H1](-[#6])-[#6;!$([#6]=[C,N,O,S]):2]),$([N;H2]-[#6;!$([#6]=[C,N,O,S]):2]):1][#6;!$([#6]=[C,N,O,S]):2].[#6:3]~[#6:4][#6;!R:5](=[O:6])-O)>>[#6:3][#6:4][#6:5](=[O:6])[#7:1][#6:2]",
334
+ "tags": [
335
+ "amide coupling",
336
+ "amide",
337
+ "lactam",
338
+ "macrolactamization",
339
+ "transformation",
340
+ "intramolecular"
341
+ ],
342
+ "tier": 1
343
+ },
344
+ "amide_coupling-4": {
345
+ "description": "Intramolecular amide coupling",
346
+ "ld_data": {
347
+ "display_smarts": "[#7]-C=1-C=C-C=C-C=1/C=C\\C(=O)-O>>C=1-2-C=C-C=C-C=1-N-C(=O)-C=C-2"
348
+ },
349
+ "long_name": "Intramolecular amide coupling to form quinolinones",
350
+ "retro_smarts": "[c;$(c(a)(c)c):7]1[c;$([c;H1]),$(c-[#6]):3][c;$([c;H1]),$(c-[#6]):4][c:5](=[O:6])[n;$([n;H0]([c;$(c=O)])(-[#6])[c;$(c(a)(c)c):2]),$([n;H1]([c;$(c=O)])[c:2]):1][c:2]1>>[N:1]-[c:2][c:7]/[C:3]=[C:4]\\[C:5](=[O:6])-[O;H1]",
351
+ "syn_smarts": "[N;$([N;H1](-[#6])-[c:2]),$([N;H2]-[c:2]):1]-[c:2][c:7]/[C;$([C;H1]),$([C;H0](-[c:7])-[#6]):3]=[C;$([C;H1]),$([C;H0](-[C:5]=O)-[#6]):4]\\[C:5](=[O:6])-[O;H1]>>[c:7]1[c:3][c:4][c:5](=[O:6])[#7:1][c:2]1",
352
+ "tags": [
353
+ "amide coupling",
354
+ "amide",
355
+ "lactam",
356
+ "macrolactamization",
357
+ "transformation",
358
+ "intramolecular"
359
+ ],
360
+ "tier": 1
361
+ },
362
+ "amination-1": {
363
+ "description": "Buchwald-Hartwig Amination: N-arylation of primary and secondary amines using aryl halides.",
364
+ "ld_data": {
365
+ "display_smarts": "[#35]-[#6:201].[#7]-[#6:101]>>[#6:101]-[#7]-[#6:201] |$;Aryl_p;;;;;Aryl_p$|"
366
+ },
367
+ "long_name": "Buchwald-Hartwig amination from aryl halides and primary or secondary amines",
368
+ "retro_smarts": "[c;$(c1[c,n][c,n][c,n][c,n][c,n]1),$(c1[c,n,o,s][c,n][c,n][c,n]1),$(c1[c,n][c,n,o,s][c,n][c,n]1):1]!@[N;$([N;H0](-c)(-[#6;!$([#6]=[C,N,O,S])])-[#6;!$([#6]=[C,N,O,S])]),$([N;H1](-c)-[#6;!$([#6]=[C,N,O,S])])!$(N~[O,S,P]);!$(N=*);!$([N-]);!$(N#*);!$([ND4]);!$(N-[C,N,O,S]=[C,N,O,S]):2]>>Cl-[c:1].[N:2]",
369
+ "rhs_classes": [
370
+ "halides-aryl",
371
+ "amines-primsec"
372
+ ],
373
+ "syn_smarts": "[Cl,Br,I]-[c;$(c1[c,n][c,n][c,n][c,n][c,n]1),$(c1[c,n,o,s][c,n][c,n][c,n]1),$(c1[c,n][c,n,o,s][c,n][c,n]1):101].[#6;!$([#6]=[#6,#7,#8,#16]):102]-[N;$([N;H1](-[#6;!$([#6]=[#6,#7,#8,#16]):103])-[#6;!$([#6]=[#6,#7,#8,#16]):102]),$([N;H2]-[#6;!$([#6]=[#6,#7,#8,#16]):102]);!$(N~[O,S,P]);!$(N=*);!$([N-]);!$(N#*);!$([ND4]);!$(N-[C,N,O,S]=[C,N,O,S]):2]>>[c:101]-[N:2]-[#6:102]",
374
+ "tags": [
375
+ "Buchwald-Hartwig",
376
+ "amination",
377
+ "N-arylation"
378
+ ],
379
+ "tier": 1
380
+ },
381
+ "amination-2": {
382
+ "description": "Reductive Amination: Alkylation of primary or secondary amines with a ketone or an aldehyde.",
383
+ "ld_data": {
384
+ "display_smarts": "O=C-[#6:101].[#6:102]-[#7]>>[#6:102]-N-C-[#6:101]"
385
+ },
386
+ "long_name": "Reductive amination",
387
+ "retro_smarts": "[#6;!$(C=[C,N,O,S]):101]-[C;$([C;H2]-[#6;!$(C=[C,N,O,S])]),$([C;H1](-[#6;!$(C=[C,N,O,S])])-[#6;!$(C=[C,N,O,S])]):1]-!@[N;$([N;H1]-[#6;!$([#6]=[#6,#7,#8,#16]):102]),$([N;H0](-[#6;!$([#6]=[#6,#7,#8,#16]):104])-[#6;!$([#6]=[#6,#7,#8,#16]):102]);!$(N-[C,N,O,S]=[C,N,O,S]);!$(N-[N,O,S]):2]-[#6;!$([#6]=[#6,#7,#8,#16]):102]>>[#6:101]-[C:1]=O.[#7:2]-[#6:102]",
388
+ "rhs_classes": [
389
+ "aldehydes-ketones",
390
+ "amines-primsec"
391
+ ],
392
+ "syn_smarts": "O=[C;!$(C-[N,O,S]);!$(C-C=[C,N,O,S]);$([C;H1]-[#6;!$(C=[C,N,O,S]):101]),$([C;H0](-[#6;!$(C=[C,N,O,S]):103])-[#6;!$(C=[C,N,O,S]):101]):1]-[#6;!$(C=[C,N,O,S]):101].[#6;!$([C]=[C,N,O,S]):102]-[N;$([N;H1](-[#6;!$([C]=[C,N,O,S]):104])-[#6;!$([C]=[C,N,O,S]):102]),$([N;H2]-[#6;!$([C]=[C,N,O,S]):102]);!$(N-[N,O,S]);!$(N-[C,N,O,S]=[C,N,O,S]):2]>>[#6:101]-[C:1]-[N:2]-[#6:102]",
393
+ "tags": [
394
+ "reductive amination",
395
+ "amination"
396
+ ],
397
+ "tier": 1
398
+ },
399
+ "aminothiophene-1": {
400
+ "description": "Gewald Aminothiophene synthesis.",
401
+ "ld_data": {
402
+ "display_smarts": "[#6:101]-C(=O)-C-[#6:102].N#C-C-C(=O)-O-[#6:103]>>[#6:102]-C-1=C(-[#6:101])-C(-C(=O)-O-[#6:103])=C(-[#7])-S-1"
403
+ },
404
+ "long_name": "Gewald aminothiophene synthesis",
405
+ "retro_smarts": "[#6;!$(C=[C,N,O,S]):1]-[c:2]1[c:3](-[#6;!$(C=[C,N,O,S]):4])[c:5](-[#6:6](=[O:10])-[O:11]-[C;!$([#6]=[#6,#7,#8,#16]):7])[c:8](-[N;H2:9])s1>>[#6:1]-[#6:2]-[#6:3](=O)-[#6:4].[#7;H0:9]#[C:8]-[C:5]-[#6:6](=[O:10])-[O:11]-[C:7]",
406
+ "rhs_classes": [
407
+ "ketones-2unsub",
408
+ "esters-2cyano"
409
+ ],
410
+ "syn_smarts": "[#6;!$(C=[C,N,O,S]):101]-[#6;H2:2]-[#6:3](=O)-[#6;!$(C=[C,N,O,S]):102].N#C-[C;H2:5]-[#6:6](=O)-O-[C;!$([#6]=[#6,#7,#8,#16]):103]>>[#6:101]-[c;H0:2]1[c:3](-[#6:102])[c;H0:5](-[#6:6](=O)-O-[#6:103])c(-[#7;H2])s1",
411
+ "tags": [
412
+ "heterocycle formation",
413
+ "aminothiophene",
414
+ "cyclization",
415
+ "thiophene"
416
+ ],
417
+ "tier": 1
418
+ },
419
+ "barton-zard-1": {
420
+ "description": "Synthesis of a substituted pyrrole from an isocyanoacetate and a nitroalkene",
421
+ "ld_data": {
422
+ "display_smarts": "[#6:101]-[O]-[#6](=[O])-[#6]-[#7;+]#[#6;-].C(/[#6:102])=C(/[#6:103])-[#7;+](=O)-[O;-]>>[#6:101]-[O]-[#6](=[O])-[#6]1=[#6](-[#6:102])-[#6](-[#6:103])=[#6]-[#7]-1"
423
+ },
424
+ "long_name": "Barton-Zard pyrrole synthesis",
425
+ "retro_smarts": "[#6;!$(C=[C,N,O,S]):1]-[O:2]-[#6:3](=[O:4])!@-[c:5]1[c;$([c;H1]),$(c-[#6;!$(C=[C,N,O,S])]):6][c;$([c;H1]),$(c-[#6;!$(C=[C,N,O,S])]):7][c;H1:8][n;H1:9]1>>[#6:1]-[O:2]-[#6:3](=[O:4])-[C:5]-[N;H0;+:9]#[C;H0;-:8].[#6:6]=[#6:7]-[N;+](=O)[O-]",
426
+ "rhs_classes": [
427
+ "isocyanoacetates",
428
+ "nitroalkenes"
429
+ ],
430
+ "syn_smarts": "[#6;!$(C=[C,N,O,S]):1]-[O:2]-[C:3](=[O:4])-[C;H2:5]-[N;+:6]#[C;-:7].[C;$([C;H2]),$([C;H1]-[#6;!$(C=[C,N,O,S])]):8]=[C;$([C;H1]),$(C-[#6;!$(C=[C,N,O,S])]):9]-[N;+](=O)[O;-]>>[#6:1]-[O:2]-[C:3](=[O:4])-[c:5]:1:[c:8]:[c:9]:[c;H1;+0:7]:[n;H1;+0:6]:1",
431
+ "tags": [
432
+ "Barton-Zard",
433
+ "pyrrole",
434
+ "heterocycle formation",
435
+ "heterocycle"
436
+ ],
437
+ "tier": 1
438
+ },
439
+ "barton-zard-2": {
440
+ "description": "Synthesis of a substituted pyrrole from an isocyanoacetate and a nitrobenzene",
441
+ "ld_data": {
442
+ "display_smarts": "[#6:101]-[O]-[#6](=[O])-[#6]-[#7;+]#[#6;-].[#6]=1-[#6]=[#6]-[#6]=[#6]-[#6]=1-[#7;+](=O)-[O-]>>[#6:101]-[O]-[#6](=O)-[#6]-1=[#6]-2-[#6]=[#6]-[#6]=[#6]-[#6]-2=[#6]-[#7]-1"
443
+ },
444
+ "long_name": "Aromatic Barton-Zard pyrrole synthesis",
445
+ "retro_smarts": "[#6;!$(C=[C,N,O,S]):1]-[O:2]-[C:3](=[O:4])!@-[#6:5]1[#6:9]2[a:10][a:11][a:12][a:13][#6:8]2[#6;H1:7][#7;H1:6]1>>[#6:1]-[O:2]-[#6:3](=[O:4])-[C;H2:5]-[N;H0;+:6]#[C;H0;-:7].[c;H1:9]1[a:10][a:11][a:12][a:13][c:8]1-[#7;+](=O)[O-]",
446
+ "rhs_classes": [
447
+ "isocyanoacetates",
448
+ "nitrobenzenes-2H"
449
+ ],
450
+ "syn_smarts": "[#6;!$(C=[C,N,O,S]):1]-[O:2]-[C:3](=[O:4])-[C;H2:5]-[N;+:6]#[C;-:7].[c;H1:8]:1:[a:9]:[a:10]:[a:11]:[a:12]:[c:13]:1-[N;+](=O)[O-]>>[#6;!$(C=[C,N,O,S]):1]-[O:2]-[C:3](=[O:4])-[c:5]:1:[c:8]:2:[a:9]:[a:10]:[a:11]:[a:12]:[c:13]:2:[c;H1;+0:7]:[n;H1;+0:6]:1",
451
+ "tags": [
452
+ "Barton-Zard",
453
+ "pyrrole",
454
+ "heterocycle formation",
455
+ "heterocycle"
456
+ ],
457
+ "tier": 1
458
+ },
459
+ "benzimidazole-1": {
460
+ "allow_multiple_products": true,
461
+ "description": "Benzimidazole synthesis from an ortho-amino aniline and a carboxylic acid or ester.",
462
+ "ld_data": {
463
+ "display_smarts": "[#6]-1=[#6]-[#6]=[#6]-[#6](-[#7])=[#6](-[#7])-1.[#6](=O)(-O)-[#6:101]>>[#6:101]-[#6]-1=[#7]-[#6]-2=[#6](-[#7]-1)-[#6]=[#6]-[#6]=[#6]-2"
464
+ },
465
+ "long_name": "2-Substituted benzimidazole formation from carboxylic acids or esters",
466
+ "retro_smarts": "[#6;!$(C=[C,N,O,S]):1]-[c:2]1[n;D2:3][c;!$(c-[C,N]);R2:4][c;!$(c-[C,N]);R2:5][n;D2:6]1>>[N:3][c:4][c:5][N:6].[C:2](=O)([O;H1])[#6:1]",
467
+ "rhs_classes": [
468
+ "anilines-2NH2",
469
+ "carboxylates"
470
+ ],
471
+ "syn_smarts": "[#7;H2:3]-[#6:1]:[#6:2]-[#7;H2:4].[O;H1]-[#6:5](=O)-[#6;!$(C=[C,N,O,S]):101]>>[#6:1]1:[#6:2]:[#7:4]:[#6:5](-[#6:101]):[#7;H1:3]:1",
472
+ "tags": [
473
+ "heterocycle formation",
474
+ "heterocycle",
475
+ "benzimidazole"
476
+ ],
477
+ "tier": 1
478
+ },
479
+ "benzimidazole-2": {
480
+ "allow_multiple_products": true,
481
+ "description": "Benzimidazole synthesis from an ortho-amino aniline and an aldehyde.",
482
+ "ld_data": {
483
+ "display_smarts": "[#6]-1=[#6]-[#6]=[#6]-[#6](-[#7])=[#6](-[#7])-1.O=[#6]-[#6:101]>>[#6:101]-[#6]-1=[#7]-[#6]-2=[#6](-[#7]-1)-[#6]=[#6]-[#6]=[#6]-2"
484
+ },
485
+ "long_name": "2-Substituted benzimidazole formation from aldehydes",
486
+ "retro_smarts": "[#6;!$(C=[C,N,O,S]):1]-[c:2]1[n;D2:3][c;!$(c-[C,N]);R2:4][c;!$(c-[C,N]);R2:5][n;D2:6]1>>[N:3][c:4][c:5][N:6].[C:2](=O)[#6:1]",
487
+ "rhs_classes": [
488
+ "anilines-2NH2",
489
+ "aldehydes"
490
+ ],
491
+ "syn_smarts": "[#7;H2:3]-[#6:1]:[#6:2]-[#7;H2:4].[#6;H1:5](=O)-[#6;!$(C=[C,N,O,S]):101]>>[#6:1]1:[#6:2]:[#7:4]:[#6:5](-[#6:101]):[#7;H1:3]:1",
492
+ "tags": [
493
+ "heterocycle formation",
494
+ "heterocycle",
495
+ "benzimidazole"
496
+ ],
497
+ "tier": 1
498
+ },
499
+ "benzimidazole-3": {
500
+ "allow_multiple_products": true,
501
+ "description": "2-Chloro-benzimidazole formation from 2-amino anilines.",
502
+ "ld_data": {
503
+ "display_smarts": "[#6]-1=[#6]-[#6]=[#6]-[#6](-[#7])=[#6](-[#7])-1>>Cl-[#6]-1=[#7]-[#6]-2=[#6](-[#7]-1)-[#6]=[#6]-[#6]=[#6]-2"
504
+ },
505
+ "long_name": "2-Chloro-benzimidazole formation",
506
+ "retro_smarts": "[#17]-c1[n;H1:1][c;!$(c-[C,N]):2][c;!$(c-[C,N]):3][n:4]1>>[#7;H2:1]-[c:2][c:3]-[#7;H2:4]",
507
+ "rhs_classes": [
508
+ "anilines-2NH2"
509
+ ],
510
+ "syn_smarts": "[#7;H2:1]-[c:2][c:3]-[#7;H2:4]>>[#7;H1:1]1-[c:2][c:3]-[#7:4]=C(-[#17])-1",
511
+ "tags": [
512
+ "heterocycle formation",
513
+ "heterocycle",
514
+ "benzimidazole",
515
+ "transformation"
516
+ ],
517
+ "tier": 1
518
+ },
519
+ "benzimidazole-4": {
520
+ "allow_multiple_products": true,
521
+ "description": "Benzimidazole formation from 2-amino anilines.",
522
+ "ld_data": {
523
+ "display_smarts": "[#6]-1=[#6]-[#6]=[#6]-[#6](-[#7])=[#6](-[#7])-1>>[#7]-1-[#6]=[#7]-[#6]-2=[#6]-1-[#6]=[#6]-[#6]=[#6]-2"
524
+ },
525
+ "long_name": "Benzimidazole formation",
526
+ "retro_smarts": "[c;H1]1[n;H1:1][c;!$(c-[C,N]):2][c;!$(c-[C,N]):3][n:4]1>>[#7;H2:1]-[c:2]:[c:3]-[#7;H2:4]",
527
+ "rhs_classes": [
528
+ "anilines-2NH2"
529
+ ],
530
+ "syn_smarts": "[#7;H2:1]-[c:2][c:3]-[#7;H2:4]>>[#7;H1:1]1-[c:2][c:3]-[#7:4]=[C;H1]-1",
531
+ "tags": [
532
+ "heterocycle formation",
533
+ "heterocycle",
534
+ "benzimidazole",
535
+ "transformation"
536
+ ],
537
+ "tier": 1
538
+ },
539
+ "benzofuran-1": {
540
+ "description": "Benzofuran synthesis from a 2-iodo phenol and an alkyne.",
541
+ "ld_data": {
542
+ "display_smarts": "[#6]-1=[#6]-[#6]=[#6]-[#6](-[#8])=[#6](-I)-1.[#6:101]-[#6]#[#6]>>[#6:101]-[#6]-1=[#6]-[#6]-2=[#6](-[#8]-1)-[#6]=[#6]-[#6]=[#6]-2"
543
+ },
544
+ "long_name": "2-Substituted benzofuran synthesis from 2I-phenols and alkynes",
545
+ "retro_smarts": "[#6;!$([#6]=[#6,#7,#8,#16]):10]-!@[c:8]1[c;H1:9][c;!$(cn):3]2[a:4][a:5][a:6][a:7][c;!$(cn):2]2[o:1]1>>[#8:1]-[c:2]1[a:7][a:6][a:5][a:4][c:3]1-I.[#6:10]-[#6:8]#[#6:9]",
546
+ "rhs_classes": [
547
+ "phenols-2I",
548
+ "alkynes-monosub"
549
+ ],
550
+ "syn_smarts": "[c;r6;!$(c[o,n,s]):1](-[#8:2]):[c;r6;!$(c[o,n,s]):4]-I.[#6;!$([#6]=[#6,#7,#8,#16]):101]-[#6:6]#[#6;H1:7]>>[#6:1]1-[#8:2]-[#6:6](-[#6:101])=[#6;H1:7]-[#6:4]:1",
551
+ "tags": [
552
+ "heterocycle formation",
553
+ "heterocycle",
554
+ "benzofuran"
555
+ ],
556
+ "tier": 1
557
+ },
558
+ "benzothiazole-1": {
559
+ "description": "Benzothiazole synthesis from a 2-thiol aniline and an aldehyde.",
560
+ "ld_data": {
561
+ "display_smarts": "[#6]-1=[#6]-[#6]=[#6]-[#6](-[#16])=[#6](-[#7])-1.O=[#6]-[#6:101]>>[#6:101]-[#6]-1=[#7]-[#6]-2=[#6](-[#16]-1)-[#6]=[#6]-[#6]=[#6]-2"
562
+ },
563
+ "long_name": "2-Substituted benzothiazole synthesis from 2SH-anilines and aldehydes",
564
+ "retro_smarts": "[#6:1]-!@[c:2]1[s;X2:3][c;!$(c-[C,N]);R2:4][c;!$(c-[C,N]);R2:5][n:6]1>>[#16;H1;X2:3]-[c:4][c:5]-[#7;H2:6].[#6;H1:2](=O)-[#6:1]",
565
+ "rhs_classes": [
566
+ "anilines-2SH",
567
+ "aldehydes"
568
+ ],
569
+ "syn_smarts": "[#7;H2:3]-[#6:2]:[#6:1]-[#16;H1;X2:4].O=[#6;H1:5]-[#6:101]>>[#6:1]1:[#6:2]:[#7;H0:3]:[#6;H0:5](-[#6:101]):[#16;H0;X2:4]:1",
570
+ "tags": [
571
+ "heterocycle formation",
572
+ "heterocycle",
573
+ "benzothiazole"
574
+ ],
575
+ "tier": 1
576
+ },
577
+ "benzothiophene": {
578
+ "description": "Benzothiophene synthesis.",
579
+ "ld_data": {
580
+ "display_smarts": "[#6]-[#16]-C-1=C(-[#53])-C=C-C=C-1.[#6:101]-[#6]#[#6]>>[#6:101]-[#6]-1=[#6]-[#6]-2=[#6](-[#16]-1)-[#6]=[#6]-[#6]=[#6]-2"
581
+ },
582
+ "long_name": "Benzothiophene synthesis",
583
+ "retro_smarts": "[c:1]12[a:6][a:5][a:4][a:3][c:2]1[c;H1:10][c:9](-!@[#6:101])[s;X2:8]2>>C[#16:8]-[c:1]1[c:2](-[#53])[a:3][a:4][a:5][a:6]1.[#6:101]-[C:9]#[C;H1:10]",
584
+ "rhs_classes": [
585
+ "thioanisoles-2I",
586
+ "alkynes-monosub"
587
+ ],
588
+ "syn_smarts": "[C;H3]-[#16;X2:8]-[c:1]1[c:2](-[#35,#53])[a:3][a:4][a:5][a:6]1.[#6:101]-[C:9]#[C;H1:10]>>[c:1]12[a:6][a:5][a:4][a:3][c:2]1[c;H1:10][c:9](-[#6:101])[#16;X2:8]2",
589
+ "tags": [
590
+ "heterocycle formation",
591
+ "heterocycle",
592
+ "benzothiophene"
593
+ ],
594
+ "tier": 1
595
+ },
596
+ "benzoxazole-1": {
597
+ "description": "Benzoxazole synthesis from a 2-amino phenol and a carboxylic acid.",
598
+ "ld_data": {
599
+ "display_smarts": "[#6]-1=[#6]-[#6]=[#6]-[#6](-[#8])=[#6](-[#7])-1.[O;H1]-[#6](=O)-[#6:101]>>[#6]-1=[#6]-[#6]=[#6]-[#6]=2-[#8]-[#6](-[#6:101])=[#7]-[#6]=2-1"
600
+ },
601
+ "long_name": "2-Substituted benzoxazole synthesis from 2NH-phenols and carboxylic acids or esters",
602
+ "retro_smarts": "[#6:6]-!@[#6:5]1:[#7:4]:[c;!$(c-[C,N]);R2:3]:[c;!$(c-[C,N]);R2:1]:[#8:2]:1>>[#7;H2:4]-[c:3]:[c:1]-[#8;H1:2].[#6:6]-[#6:5](=O)-[O;H1]",
603
+ "rhs_classes": [
604
+ "anilines-2OH",
605
+ "carboxylates"
606
+ ],
607
+ "syn_smarts": "[#7;H2:4]-[c:3]:[c:1]-[#8;H1:2].[#6:101]-[#6:5](=O)-[O;H1]>>[#6:101]-[#6:5]1:[#7;H0:4]:[c:3]:[c:1]:[#8;H0:2]:1",
608
+ "tags": [
609
+ "heterocycle formation",
610
+ "heterocycle",
611
+ "benzoxazole"
612
+ ],
613
+ "tier": 1
614
+ },
615
+ "benzoxazole-2": {
616
+ "description": "Benzoxazole synthesis from a 2-amino phenol and an aryl aldehyde.",
617
+ "ld_data": {
618
+ "display_smarts": "[#7]-[#6]-1=[#6](-[#8])-[#6]=[#6]-[#6]=[#6]-1.[#6:201]-[#6]=O>>[#6:201]-[#6]-1=[#7]-[#6]-2=[#6](-[#8]-1)-[#6]=[#6]-[#6]=[#6]-2 |$;;;;;;;;Aryl_p;;;Aryl_p;;;;;;;;;$|"
619
+ },
620
+ "long_name": "2-Aryl benzoxazole synthesis from 2-aminophenols and aryl aldehydes",
621
+ "retro_smarts": "[c:1]-!@[c:2]1[o:3][c;!$(c-[C,N]);R2:4][c;!$(c-[C,N]);R2:5][n:6]1>>[#8;H1:3]-[c:4][c:5]-[#7;H2:6].[C;H1:2](=O)[c:1]",
622
+ "rhs_classes": [
623
+ "anilines-2OH",
624
+ "aldehydes-aryl"
625
+ ],
626
+ "syn_smarts": "[#8;H1:3]-[c:4]:[c:5]-[#7;H2:6].[#6;H1:2](=O)-[c:101]>>[c:101]-[#6;H0:2]1:[#8;H0:3]:[#6:4]:[#6:5]:[#7;H0:6]:1",
627
+ "tags": [
628
+ "heterocycle formation",
629
+ "heterocycle",
630
+ "benzoxazole"
631
+ ],
632
+ "tier": 1
633
+ },
634
+ "carbamate": {
635
+ "description": "Carbamate synthesis from isocyanates and primary or secondary alcohols.",
636
+ "ld_data": {
637
+ "display_smarts": "[#6:101]-N=C=O.[#6:102]-[#8]>>[#6:102]-O-C(=O)-N-[#6:101]"
638
+ },
639
+ "long_name": "Carbamate synthesis from isocyanates and primary or secondary alcohols",
640
+ "retro_smarts": "[#6;!$([#6]=[#7,#8,#16]):101]-[N;H1:1]-[C;!R:3](=[O:4])-!@[O:2]-[#6;!$([#6]=[#6,#7,#8,#16]):102]>>[#6:101]-[N;H0:1]=[C:3]=[O:4].[O;H1:2]-[#6:102]",
641
+ "rhs_classes": [
642
+ "isocyanates",
643
+ "alcohols-primsec"
644
+ ],
645
+ "syn_smarts": "[#6;!$([#6]=[#7,#8,#16]):101]-[N:2]=[C;!R]=O.[#6;!$([#6]=[#7,#8,#16]):102]-[O;H1;!$(O-[C,N,O,S]=[C,N,O,S]):3]>>[#6:101]-[N;H1:2]-C(=O)-[O;H0:3]-[#6:102]",
646
+ "tags": [
647
+ "carbamate"
648
+ ],
649
+ "tier": 1
650
+ },
651
+ "carbamate-2": {
652
+ "description": "Carbamate synthesis from primary or secondary amines and primary or secondary alcohols.",
653
+ "ld_data": {
654
+ "display_smarts": "[#6:101]-[#7].[#6:102]-[#8]>>[#6:102]-O-C(=O)-N-[#6:101]"
655
+ },
656
+ "long_name": "Carbamate synthesis from primary or secondary amines and primary or secondary alcohol",
657
+ "retro_smarts": "[#6;!$([#6]=[#7,#8,#16]):101]-[N;$([N;H1](-C=O)-[#6;!$([#6]=[#6,#7,#8,#16]):101]),$([N;H0](-C=O)(-[#6;!$([#6]=[#6,#7,#8,#16]):103])-[#6;!$([#6]=[#6,#7,#8,#16]):101]):2]-!@C(=O)-[O;H0:3]-[#6;!$([#6]=[#6,#7,#8,#16]):102]>>[#6:101]-[N:2].[O;H1:3]-[#6:102]",
658
+ "rhs_classes": [
659
+ "amines-primsec",
660
+ "alcohols-primsec"
661
+ ],
662
+ "syn_smarts": "[#6;!$([#6]=[C,N,O,S]):101]-[N;$([N;H1](-[#6;!$([#6]=[C,N,O,S]):101])-[#6;!$([#6]=[C,N,O,S]):103]),$([N;H2]-[#6;!$([#6]=[C,N,O,S]):101]):2].[#6;!$([#6]=[#7,#8,#16]):102]-[O;H1;!$(O-[C,N,O,S]=[C,N,O,S]):3]>>[#6:101]-[N;$([N;H1](-C=O)-[#6:101]),$([N;H0](-C=O)(-[#6:103])-[#6:101]):2]-C(=O)-[O;H0:3]-[#6:102]",
663
+ "tags": [
664
+ "carbamate"
665
+ ],
666
+ "tier": 1
667
+ },
668
+ "castro-stephens-1": {
669
+ "description": "Castro-Stephens coupling: synthesis of indoles.",
670
+ "ld_data": {
671
+ "display_smarts": "[#7]-C-1=C(-[#53])-C=C-C=C-1.[#6:101]-[#6]#[#6]>>C=1-2-C=C-C=C-C=1-C=C(-[#6:101])-N-2"
672
+ },
673
+ "long_name": "Castro-Stephens coupling: synthesis of indoles",
674
+ "retro_smarts": "[c:1]12[a:6][a:5][a:4][a:3][c:2]1[c;H1:10][c:9](-!@[#6:101])[n;H1:8]2>>[#7;H2:8]-[c:1]1[c:2](-[#53])[a:3][a:4][a:5][a:6]1.[#6:101]-[C:9]#[C;H1:10]",
675
+ "rhs_classes": [
676
+ "anilines-2I",
677
+ "alkynes-monosub"
678
+ ],
679
+ "syn_smarts": "[#7;H2:8]-[c:1]1[c:2](-[#35,#53])[a:3][a:4][a:5][a:6]1.[#6:101]-[C:9]#[C;H1:10]>>[c:1]12[a:6][a:5][a:4][a:3][c:2]1[c:10][c:9](-[#6:101])[n;H1:8]2",
680
+ "tags": [
681
+ "Castro-Stephens",
682
+ "heterocycle formation",
683
+ "heterocycle",
684
+ "indole"
685
+ ],
686
+ "tier": 1
687
+ },
688
+ "castro-stephens-2": {
689
+ "description": "Castro-Stephens coupling: synthesis of disubstituted acetylenes.",
690
+ "ld_data": {
691
+ "display_smarts": "[#6:201]-[#35].[#6:101]-[#6]#[#6]>>[#6:201]-[#6]#[#6]-[#6:101] |$Aryl_p;;;;;Aryl_p;;;$|"
692
+ },
693
+ "long_name": "Castro-Stephens coupling: synthesis of disubstituted acetylenes",
694
+ "retro_smarts": "[#6;$(c),$(C=C):101]-!@[C:3]#[C:2]-[#6:102]>>[#6:101]-[#35].[#6:102]-[C:2]#[C;H1:3]",
695
+ "rhs_classes": [
696
+ "halides-aryl-vinyl",
697
+ "alkynes-monosub"
698
+ ],
699
+ "syn_smarts": "[#6;$(c),$(C=C):101]-[#35,#53].[#6:102]-[C:2]#[C;H1:3]>>[#6:101]-[C;H0:3]#[C:2]-[#6:102]",
700
+ "tags": [
701
+ "Castro-Stephens",
702
+ "alkyne",
703
+ "acetylene"
704
+ ],
705
+ "tier": 1
706
+ },
707
+ "chan-lam-1": {
708
+ "description": "Chan-Lam coupling: N-arylation of anilines with boronic acids.",
709
+ "ld_data": {
710
+ "display_smarts": "[#6:201]-[#7].[#6:202]-B(-O)-O>>[#6:201]-[#7]-[#6:202] |$Aryl_p;;Aryl_p;;;;Aryl_p;;Aryl_p$|"
711
+ },
712
+ "long_name": "Chan-Lam coupling: N-arylation of anilines with boronic acids",
713
+ "retro_smarts": "[c;r6:1]-[N;H1:2]-!@[c;r6:3]>>[c:1]-[N;H2:2].[c:3]-B(-O)-O",
714
+ "rhs_classes": [
715
+ "anilines-prim",
716
+ "boronates-aryl"
717
+ ],
718
+ "syn_smarts": "[c;r6:201]-[N;H2:2].[c;r6:202]-B(~O)~O>>[c:201]-[N;H1:2]-[c:202]",
719
+ "tags": [
720
+ "Chan-Lam",
721
+ "C-N bond formation",
722
+ "C-N",
723
+ "N-arylation"
724
+ ],
725
+ "tier": 1
726
+ },
727
+ "chan-lam-2": {
728
+ "description": "Chan-Lam coupling: O-arylation of phenols with boronic acids.",
729
+ "ld_data": {
730
+ "display_smarts": "[#6:201]-[#8].[#6:202]-B(-O)-O>>[#6:201]-[#8]-[#6:202] |$Aryl_p;;Aryl_p;;;;Aryl_p;;Aryl_p$|"
731
+ },
732
+ "long_name": "Chan-Lam coupling: O-arylation of phenols with boronic acids",
733
+ "retro_smarts": "[c;r6:1]-[O;H0:2]-!@[c;r6:3]>>[c:1]-[O;H1:2].[c:3]-B(-O)-O",
734
+ "rhs_classes": [
735
+ "phenols",
736
+ "boronates-aryl"
737
+ ],
738
+ "syn_smarts": "[c;r6:201]-[O;H1:2].[c;r6:202]-B(~O)~O>>[c:201]-[O;H0:2]-[c:202]",
739
+ "tags": [
740
+ "Chan-Lam",
741
+ "C-O bond formation",
742
+ "C-O",
743
+ "O-arylation"
744
+ ],
745
+ "tier": 1
746
+ },
747
+ "chan-lam-3": {
748
+ "description": "Chan-Lam coupling: S-arylation of thiophenols with boronic acids.",
749
+ "ld_data": {
750
+ "display_smarts": "[#6:201]-[#16].[#6:202]-B(-O)-O>>[#6:201]-[#16]-[#6:202] |$Aryl_p;;Aryl_p;;;;Aryl_p;;Aryl_p$|"
751
+ },
752
+ "long_name": "Chan-Lam coupling: S-arylation of thiophenols with boronic acids",
753
+ "retro_smarts": "[c;r6:1]-[S;H0;X2:2]-!@[c;r6:3]>>[c:1]-[S;H1;X2:2].[c:3]-B(-O)-O",
754
+ "rhs_classes": [
755
+ "thiophenols",
756
+ "boronates-aryl"
757
+ ],
758
+ "syn_smarts": "[c;r6:201]-[S;H1;X2:2].[c;r6:202]-B(~O)~O>>[c:201]-[S;H0;X2:2]-[c:202]",
759
+ "tags": [
760
+ "Chan-Lam",
761
+ "C-S bond formation",
762
+ "C-S",
763
+ "S-arylation"
764
+ ],
765
+ "tier": 1
766
+ },
767
+ "claisen-1": {
768
+ "description": "Crossed Claisen condensation: 1,3-diketone synthesis from an enolizable ketone and a non-enolizable ester.",
769
+ "ld_data": {
770
+ "display_smarts": "[#6:102]-C-C(=O)-[#6:101].[#6]-[#8]-[#6](-[#6:103])=O>>[#6:101]-C(=O)-C(-[#6:102])-[#6](-[#6:103])=O"
771
+ },
772
+ "long_name": "Crossed Claisen condensation",
773
+ "retro_smarts": "[#6;!$([#6]=[#6,#7,#8,#16]):1]-[#6:2](=[O:6])-[#6;H1,H2;!$([#6]=[#6,#7,#8,#16]):3]-!@[#6;!R:4](=[O:7])-[#6;$(C#C),$(c):5]>>[#6:1]-[#6:2](=[O:6])-[#6:3].[#6:5]-[#6:4](=[O:7])-O-C",
774
+ "rhs_classes": [
775
+ "ketones-enolizable",
776
+ "esters-non-enolizable"
777
+ ],
778
+ "syn_smarts": "[#6;!$([#6]=[#6,#7,#8,#16]):102]-[#6:2](=O)-[#6;$([C;H2]),$([C;H3]);!$([#6]=[#6,#7,#8,#16]):10].[#6;$(C#C),$(c):101]-[#6;!R:3](=O)-O-[C;!$([#6]=[#6,#7,#8,#16])]>>[#6:102]-[#6:2](=O)-[#6:10]-[#6:3](=O)-[#6:101]",
779
+ "tags": [
780
+ "Claisen",
781
+ "condensation",
782
+ "diketone"
783
+ ],
784
+ "tier": 2
785
+ },
786
+ "claisen-2": {
787
+ "description": "Claisen condensation: beta-keto ester synthesis from an enolizable ester and a non-enolizable ester.",
788
+ "ld_data": {
789
+ "display_smarts": "[#6]-[#6](=O)-[#8]-[#6:101].[#6:201]-[#6](=O)-O-[#6]>>[#6:201]-[#6](=O)-[#6]-[#6](=O)-[#8]-[#6:101] |$;;;;;Aryl_p;;;;;Aryl_p;;;;$|"
790
+ },
791
+ "long_name": "Claisen condensation",
792
+ "retro_smarts": "[#6;!$([#6]=[#6,#7,#8,#16]):1]-[O:2]-[C:3](=[O:7])-[#6;!$([#6]=[#6,#7,#8,#16]):4]-!@[#6:5](=[O:8])-[#6;$(C#C),$(c):6]>>[#6:1]-[O:2]-[C:3](=[O:7])-[#6:4].CO-[#6:5](=[O:8])-[#6:6]",
793
+ "rhs_classes": [
794
+ "esters-enolizable",
795
+ "esters-non-enolizable"
796
+ ],
797
+ "syn_smarts": "[#6;$([C;H2]),$([C;H3]);!$([#6]=[#6,#7,#8,#16]);!$([#6]-[#9,#17,#35,#53]):1]-[#6:3](=O)-[O:5]-[#6;!$([#6]=[#6,#7,#8,#16]):102].[#6;$(C#C),$(c):103]-[#6:2](=O)-O-[C;!$([#6]=[#6,#7,#8,#16])]>>[#6:103]-[#6:2](=O)-[#6:1]-[#6:3](=O)-[#8:5]-[#6:102]",
798
+ "tags": [
799
+ "Claisen",
800
+ "condensation",
801
+ "beta-ketoester",
802
+ "ester"
803
+ ],
804
+ "tier": 2
805
+ },
806
+ "conrad-limpach": {
807
+ "description": "Conrad-Limpach synthesis of substituted 4-hydroxyquinolines.",
808
+ "ld_data": {
809
+ "display_smarts": "[#6:101]-[#6](=O)-[#6]-[#6](=O)-O-[#6].[#7]-C-1=C-C=C-C=C-1>>C=1-2-C=C-C=C-C=1-C(-[#8])=C-C(-[#6:101])=N-2"
810
+ },
811
+ "long_name": "Conrad-Limpach synthesis of substituted 4-hydroxyquinolines",
812
+ "retro_smarts": "[c;!$(c-[C,N]);R2:6]2[c;!$(c-[C,N]);R2:7][c:4](-[O;H1:8])[c:3][c:2](-[#6:101])[n:5]2>>[#6:101]-[#6:2](=O)-[#6:3]-[#6:4](=[O;H0:8])-O-C.[N;H2:5]-[c;R1:6][c;R1;H1:7]",
813
+ "rhs_classes": [
814
+ "esters-3keto",
815
+ "anilines-2H"
816
+ ],
817
+ "syn_smarts": "[#6:101]-[#6:2](=O)-[C;$([C;H2]),$([C;H1](-C=O)(-C=O)-[C;!H0;!$(C=N)]):3]-[#6:4](=O)-O-C.[N;H2:5]-[c;R1:6][c;R1;H1:7]>>[c;R2:6]2[c;R2;H0:7]-[C:4](-[O;H1])=[C:3]-[C:2](-[#6:101])=[N;H0:5]-2",
818
+ "tags": [
819
+ "Conrad-Limpach",
820
+ "heterocycle formation",
821
+ "heterocycle",
822
+ "4-hydroxyquinoline",
823
+ "quinoline"
824
+ ],
825
+ "tier": 1
826
+ },
827
+ "corey-chaykovsky-1": {
828
+ "description": "Corey-Chaykovsky synthesis of an epoxide from an aldehyde or a ketone.",
829
+ "ld_data": {
830
+ "display_smarts": "[#6:101]-C(=O)-[#6:102]>>[#6:101]-C(-[#6:102])-1-O-C-1"
831
+ },
832
+ "long_name": "Corey-Chaykovsky epoxidation",
833
+ "retro_smarts": "[#6;!$(C=[C,N,O,S]):101]-[C;$([C;H0](-[C;H2])(-[#6;!$(C=[C,N,O,S]):101])-[#6;!$(C=[C,N,O,S]):102]),$([C;H1](-[#6;!$(C=[C,N,O,S]):101])-[C;H2]):2]1-[O:3]-[C;H2]1>>[#6:101]-[C:2]=[O:3]",
834
+ "rhs_classes": [
835
+ "aldehydes-ketones"
836
+ ],
837
+ "syn_smarts": "[#6;!$(C=[C,N,O,S]):101]-[C;$([C;H0](-[#6;!$(C=[C,N,O,S]):101])-[#6;!$(C=[C,N,O,S]):102]),$([C;H1]-[#6;!$(C=[C,N,O,S]):101]):2]=O>>[#6:101]-[C:2]1-O-[C;H2]1",
838
+ "tags": [
839
+ "Corey-Chaykovsky",
840
+ "epoxide",
841
+ "epoxidation",
842
+ "transformation"
843
+ ],
844
+ "tier": 1
845
+ },
846
+ "corey-chaykovsky-2": {
847
+ "description": "Corey-Chaykovsky cyclopropane synthesis.",
848
+ "ld_data": {
849
+ "display_smarts": "[#6:101]-C(=O)/C=C/[#6:102]>>[#6:101]-C(=O)-C-1-C-C-1(-[#6:102])"
850
+ },
851
+ "long_name": "Corey-Chaykovsky cyclopropanation",
852
+ "retro_smarts": "[#6:101]-[C:2](=[O:1])-[C;H1:3]1-[C;H2]-[C;$([C;H1](-[C;H2])(-[C:3])-[#6:102]),$([C;H2](-[C;H2])-[C:3]):4]-1>>[#6:101]-[C:2](=[O:1])-[C:3]=[C:4]",
853
+ "rhs_classes": [
854
+ "ketones-unsaturated"
855
+ ],
856
+ "syn_smarts": "[#6:101]-[C:2](=O)-[C;H1:3]=[C;$([C;H2]),$([C;H1]-[#6:102]):4]>>[#6:101]-[C:2](=O)-[C:3]1-[C;H2]-[C:4]1",
857
+ "tags": [
858
+ "Corey-Chaykovsky",
859
+ "cyclopropane",
860
+ "transformation"
861
+ ],
862
+ "tier": 1
863
+ },
864
+ "coumarin": {
865
+ "description": "Pechmann condensation: Coumarin synthesis from a phenol and a beta-keto ester.",
866
+ "ld_data": {
867
+ "display_smarts": "[#6:101]-[#6](=O)-[#6]-[#6](=O)-O-[#6].[#6](-[#8])1-[#6]=[#6]-[#6]=[#6]-[#6]=1>>[#6:101]-[#6]-1=[#6]-[#6](=O)-[#8]-[#6]-2=[#6]-1-[#6]=[#6]-[#6]=[#6]-2"
868
+ },
869
+ "long_name": "Pechmann coumarin synthesis",
870
+ "retro_smarts": "[#6:1]-!@[c:2]1[c;H1:3][c:4](=[O:12])[o:6][c:5]2[c:7][c:8][c:9][c:10][c:11]21>>[#6:1]-[C:2](=O)-[C:3]-[C:4](=[O:12])-OC.[c:5](-[O;H1:6])1[c:7][c:8][c:9][c:10][c;H1:11]1",
871
+ "rhs_classes": [
872
+ "esters-3keto",
873
+ "phenols-2H"
874
+ ],
875
+ "syn_smarts": "[#6:101]-[#6:2](=O)-[#6;H2:3]-[#6:4](=O)-O-C.[c:5](-[#8;H1:6])1[c:7][c:8][c:9][c:10][c;H1:11]1>>[#6:101]-[#6:2]1=[#6;H1:3]-[#6:4](=O)-[#8;H0:6]-[#6:5]2-[#6:7]=[#6:8]-[#6:9]=[#6:10]-[#6;H0:11]=2-1",
876
+ "tags": [
877
+ "Pechmann",
878
+ "heterocycle formation",
879
+ "heterocycle",
880
+ "coumarin"
881
+ ],
882
+ "tier": 1
883
+ },
884
+ "curtius-1": {
885
+ "description": "Curtius rearrangement: ureas via isocyanates formed from carboxylates",
886
+ "ld_data": {
887
+ "display_smarts": "[#6:101]-[#6](=O)-[O;H1].[#7]-[#6:102]>>[#6:101]-[#7]-[#6](=[#8])-[#7]-[#6:102]"
888
+ },
889
+ "long_name": "Curtius rearrangement of carboxylates to isocynates and addition of amines to form carbamates and carbonates",
890
+ "retro_smarts": "[#6;!$([#6]=[#7,#8,#16]):101]-[N;H1]-!@[C:2](=[O:3])-!@[N;$([N;H0](-[#6;!$([#6]=[C,N,O,S]):104])-[#6;!$([#6]=[C,N,O,S]):102]),$([N;H1]-[#6;!$([#6]=[C,N,O,S]):102]):4]-[#6;!$([#6]=[C,N,O,S]):102]>>[#6:101]-[C:2](=[O:3])-[O;H1].[#7:4]-[#6:102]",
891
+ "rhs_classes": [
892
+ "carboxylates",
893
+ "amines-primsec"
894
+ ],
895
+ "syn_smarts": "[#6;!$([#6]=[#7,#16]):101]-[#6:2](=[#8:3])-[O;H1].[#6;!$([#6]=[C,N,O,S]):102]-[N;$([N;H1](-[#6;!$([#6]=[C,N,O,S]):102])-[#6;!$([#6]=[C,N,O,S]):104]),$([N;H2]-[#6;!$([#6]=[C,N,O,S]):101]):4]>>[#6:101]-[#7;H1]-[#6:2](=[#8:3])-[#7:4]-[#6:102]",
896
+ "tags": [
897
+ "Curtius Rearrangement",
898
+ "ureas"
899
+ ],
900
+ "tier": 1
901
+ },
902
+ "curtius-2": {
903
+ "description": "Curtius rearrangement: carbamates via isocyanates formed from carboxylates",
904
+ "ld_data": {
905
+ "display_smarts": "[#6:101]-[#6](=O)-[O;H1].[#8;H1](-[#6:102])>>[#6:101]-[#7;H1]-[#6](=[#8])-[#8](-[#6:102])"
906
+ },
907
+ "long_name": "Curtius rearrangement of carboxylates to isocynates and addition of alcohols to form carbamates",
908
+ "retro_smarts": "[#6;!$([#6]=[#7,#8,#16]):101]-[N;H1]-!@[C:2](=[O:3])-!@[#8;H0:4]-[#6;!$([#6]=[C,N,O,S]):102]>>[#6:101]-[C:2](=[O:3])-[O;H1].[#8;H1:4]-[#6:102]",
909
+ "rhs_classes": [
910
+ "carboxylates",
911
+ "alcohols-primsec"
912
+ ],
913
+ "syn_smarts": "[#6;!$([#6]=[#7,#16]):101]-[#6:2](=[O:3])-[O;H1].[#6;!$([#6]=[#7,#8,#16]):102]-[O;H1;!$(O-[C,N,O,S]=[C,N,O,S]):4]>>[#6:101]-[#7;H1]-[#6:2](=[O:3])-[O;H0:4]-[#6:102]",
914
+ "tags": [
915
+ "Curtius Rearrangement",
916
+ "carbamates"
917
+ ],
918
+ "tier": 1
919
+ },
920
+ "curtius-3": {
921
+ "description": "Curtius rearrangement: formation of primary amines via hydrolysis of isocyanates formed from carboxylates",
922
+ "ld_data": {
923
+ "display_smarts": "[#6:101]-[#6](=[#8])-[#8]>>[#6:101]-[#7]"
924
+ },
925
+ "long_name": "Hydrolysis of isocyanates formed by Curtius rearrangement starting from carboxylates",
926
+ "retro_smarts": "[#6;!$([#6]=[#7,#16]):101]-[#7;H2]>>[#6:101]-[#6](=[#8])-[O;H1]",
927
+ "rhs_classes": [
928
+ "carboxylates"
929
+ ],
930
+ "syn_smarts": "[#6;!$([#6]=[#7,#16]):101]-C(=O)-[O;H1]>>[#6:101]-[#7;H2]",
931
+ "tags": [
932
+ "Curtius Rearrangement",
933
+ "amines",
934
+ "transformation"
935
+ ],
936
+ "tier": 1
937
+ },
938
+ "cyanohydrin": {
939
+ "description": "Cyanohydrin formation from an aldehyde.",
940
+ "ld_data": {
941
+ "display_smarts": "[#6:101]-[#6]=[#8]>>[#6:101]-[#6](-[#8])-C#N"
942
+ },
943
+ "long_name": "Cyanohydrin formation from an aldehyde",
944
+ "retro_smarts": "[#6!$(C=[C,N,O,S]):101]-[#6:1](-[O;H1:2])-C#N>>[#6:101]-[#6;H1:1]=[#8;H0:2]",
945
+ "rhs_classes": [
946
+ "aldehydes"
947
+ ],
948
+ "syn_smarts": "[#6;!$(C=[C,N,O,S]):101]-[#6;$([C;H1]):1]=[#8:2]>>[#6:101]-[#6:1](-[#8;H1:2])-C#N",
949
+ "tags": [
950
+ "cyanohydrin",
951
+ "transformation"
952
+ ],
953
+ "tier": 1
954
+ },
955
+ "decarboxylative_coupling-1": {
956
+ "description": "Aryl C-C bond formation from an aryl carboxylic acid and an aryl halide.",
957
+ "ld_data": {
958
+ "display_smarts": "[#8]-C(-[#6:201])=O.[#35]-[#6:202]>>[#6:201]-[#6:202] |$;;Aryl_p;;;Aryl_p;Aryl_p;Aryl_p$|"
959
+ },
960
+ "long_name": "Decarboxylative cross coupling reaction",
961
+ "retro_smarts": "[c;r6:1]-!@[c;r6:2]>>[#6:1]-C(=O)-[O;H1].[#6:2]-Cl",
962
+ "rhs_classes": [
963
+ "carboxylates-aryl",
964
+ "halides-aryl"
965
+ ],
966
+ "syn_smarts": "[c;r6:101]-C(=O)-[O;H1].[c;r6:102]-[Cl,Br,I]>>[c:101]-[c:102]",
967
+ "tags": [
968
+ "C-C bond formation",
969
+ "C-C",
970
+ "cross coupling"
971
+ ],
972
+ "tier": 1
973
+ },
974
+ "diyne": {
975
+ "description": "Heterocoupling of two alkynes to form a 1,3-diyne (implicit formation of a haloalkyne).",
976
+ "ld_data": {
977
+ "display_smarts": "[#6:101]-C#C.[#6:102]-C#C>>[#6:101]-C#C-C#C-[#6:102]"
978
+ },
979
+ "long_name": "Heterocoupling of two alkynes to form a 1,3-diyne (implicit formation of a haloalkyne)",
980
+ "retro_smarts": "[#6;!$(C=[C,N,O,S]):101]-[C:2]#[C:3]-!@[C:5]#[C:4]-[#6;!$(C=[C,N,O,S]):102]>>[#6:101]-[C:2]#[C;H1:3].[#6:102]-[C:4]#[C;H1:5]",
981
+ "rhs_classes": [
982
+ "alkynes-monosub",
983
+ "alkynes-monosub"
984
+ ],
985
+ "syn_smarts": "[#6;!$(C=[C,N,O,S]):101]-[C:2]#[C;H1:3].[#6;!$(C=[C,N,O,S]):102]-[C:4]#[C;H1:5]>>[#6:101]-[C:2]#[C;H0:3]-[C;H0:5]#[C:4]-[#6:102]",
986
+ "tags": [
987
+ "diyne"
988
+ ],
989
+ "tier": 1
990
+ },
991
+ "epoxidation": {
992
+ "description": "Epoxidation of alkenes.",
993
+ "ld_data": {
994
+ "display_smarts": "[#6:101]-C=C(-[#6:102])-[#6:103]>>[#6:101]-C-1-O-C-1(-[#6:102])-[#6:103]"
995
+ },
996
+ "long_name": "Epoxidation of alkenes",
997
+ "retro_smarts": "[C;$([C;H2:2](-O)-[C:3]),$([C;H1:2](-[C:3])(-O)-[#6:101]),$([C;H0:2](-[#6:104])(-[C:3])(-O)-[#6:101]):2]1-O-[C;$([C;H1:3](-[C:2])(-O)-[#6:103]),$([C;H0:3](-[#6:102])(-[C:2])(-O)-[#6:103]):3]1-!@[#6;$(c),$([C;!H0]),$(C(=O)OC):103]>>[C:2]=[C:3]-[#6:103]",
998
+ "syn_smarts": "[C;$([C;H2:2]),$([C;H1:2]-[#6:103]),$([C;H0](-[#6:104])-[#6:103]):2]=[C;$([C;H1:3]),$([C;H0:3](-[#6:102])-[#6:101]):3]-[#6;$(c),$([C;!H0]),$(C(=O)OC):101]>>[C:2]1-O-[C:3]1-[#6:101]",
999
+ "tags": [
1000
+ "epoxide",
1001
+ "epoxidation",
1002
+ "transformation"
1003
+ ],
1004
+ "tier": 1
1005
+ },
1006
+ "erlenmeyer-plochl": {
1007
+ "description": "Erlenmeyer-Plochl azlactone synthesis from aldehydes or ketones and N-acyl glycine.",
1008
+ "ld_data": {
1009
+ "display_smarts": "[#6:101]-C(=O)-[#6:102].[#8]-[#6](=O)-C-[#7]-[#6](=O)-[#6:103]>>[#6:101]-[#6](-[#6:102])=[#6]-1-[#7]=[#6](-[#6:103])-[#8]-[#6]-1=O"
1010
+ },
1011
+ "long_name": "Erlenmeyer-Plochl azlactone synthesis from aldehydes or ketones and N-acyl glycine",
1012
+ "retro_smarts": "[#6;$([#6;H2]),$([#6;H1]-[#6;!$(C-C=[O,N,S]):102]),$([#6;H0](-[#6;!$(C-C=[O,N,S]):103])-[#6;!$(C-C=[O,N,S]):102]):1]=[#6;H0:4]-1-[#7;H0:5]=[#6:6](-[#6;!$(C(-C=N)-C=[O,N,S]):101])-[#8:2]-[#6:3]-1=[O:7]>>[#6:1]=O.[#8;H1:2]-[#6:3](=[O:7])[C;H2:4]-[#7;H1:5]-[#6:6](=O)-[#6:101]",
1013
+ "rhs_classes": [
1014
+ "aldehydes-ketones",
1015
+ "glycines-N-acyl"
1016
+ ],
1017
+ "syn_smarts": "[#6;$([#6;H2]),$([#6;H1]-[#6;!$(C-C=[O,N,S]):102]),$([#6;H0](-[#6;!$(C-C=[O,N,S]):103])-[#6;!$(C-C=[O,N,S]):102]):1]=O.[#8;H1:2]-[#6:3](=O)[C;H2:4]-[#7;H1:5]-[#6:6](=O)-[#6;!$(C-C=[O,N,S]):101]>>[#6:1]=[#6;H0:4]-1-[#7;H0:5]=[#6:6](-[#6:101])-[#8;H0:2]-[#6:3]-1=O",
1018
+ "tags": [
1019
+ "Erlenmeyer-Plochl",
1020
+ "heterocycle formation",
1021
+ "heterocycle",
1022
+ "azlactone"
1023
+ ],
1024
+ "tier": 1
1025
+ },
1026
+ "ester-hydrolysis-1": {
1027
+ "description": "Hydrolysis of an ester to the parent carboxylic acid.",
1028
+ "ld_data": {
1029
+ "display_smarts": "[#6]-O-C(=O)-[#6:101]>>[#6:101]-C(=O)-O"
1030
+ },
1031
+ "long_name": "Hydrolysis of an ester to the parent carboxylic acid.",
1032
+ "retro_smarts": "[#6;!$([#6]=[#7,#16]):101]-[#6:2](=[O:1])-[O;H1]>>[#6]-O-[#6:2](=[O:1])-[#6:101]",
1033
+ "syn_smarts": "[#6;!$([#6]=[#6,#7,#8,#16])]-O-!@[#6:2](=O)-[#6;!$([#6]=[#7,#16]):1]>>[#6:1]-[#6:2](=O)-[O;H1]",
1034
+ "tags": [
1035
+ "hydrolysis",
1036
+ "ester",
1037
+ "acid",
1038
+ "transformation"
1039
+ ],
1040
+ "tier": 1
1041
+ },
1042
+ "ester-hydrolysis-2": {
1043
+ "description": "Hydrolysis of an ester to the parent alcohol.",
1044
+ "ld_data": {
1045
+ "display_smarts": "[#6:101]-O-C(=O)-[#6:102]>>O-[#6:101]"
1046
+ },
1047
+ "long_name": "Hydrolysis of an ester to the parent alcohol.",
1048
+ "retro_smarts": "[#6;!$([#6]=[#6,#7,#8,#16]):4]-[#8;H1:3]>>[#6:4]-[#8;H0:3]-C(=O)-[#6]",
1049
+ "syn_smarts": "[#6;!$([#6]=[#6,#7,#8,#16]):4]-[#8;H0:3]-!@[#6](=O)-[#6;!$([#6]=[#7,#16])]>>[#6:4]-[#8;H1:3]",
1050
+ "tags": [
1051
+ "hydrolysis",
1052
+ "ester",
1053
+ "alcohol",
1054
+ "transformation"
1055
+ ],
1056
+ "tier": 1
1057
+ },
1058
+ "esterification-1": {
1059
+ "description": "Esterification of an alcohol using an acid chloride.",
1060
+ "ld_data": {
1061
+ "display_smarts": "[#6:101]-C(=O)-Cl.[#6:102]-O>>[#6:102]-O-C(=O)-[#6:101]"
1062
+ },
1063
+ "long_name": "Esterification reaction from alcohols and acid chlorides",
1064
+ "retro_smarts": "[#6;!$([#6]=[#6,#7,#8,#16]):4]-[#8;H0:3]-!@[#6:2](=[O:5])-[#6;!$([#6]=[#7,#16]):1]>>[#6:1]-[#6:2](=[O:5])-Cl.[#6:4]-[#8;H1:3]",
1065
+ "rhs_classes": [
1066
+ "acid_chlorides",
1067
+ "alcohols"
1068
+ ],
1069
+ "syn_smarts": "[#6;!$([#6]=[#7,#16]):101]-[#6:2](=O)-Cl.[#6;!$([#6]=[#6,#7,#8,#16]):102]-[#8;H1:3]>>[#6:102]-[#8;H0:3]-[#6:2](=O)-[#6:101]",
1070
+ "tags": [
1071
+ "esterification",
1072
+ "ester"
1073
+ ],
1074
+ "tier": 1
1075
+ },
1076
+ "esterification-2": {
1077
+ "description": "Esterification of an alcohol and a carboxylic acid.",
1078
+ "ld_data": {
1079
+ "display_smarts": "[#6:101]-C(=O)-O.[#6:102]-O>>[#6:102]-O-C(=O)-[#6:101]"
1080
+ },
1081
+ "long_name": "Esterification reaction from alcohols and a carboxylic acid",
1082
+ "retro_smarts": "[#6;!$([#6]=[#6,#7,#8,#16]):4]-[#8;H0:3]-!@[#6:2](=[O:5])-[#6;!$([#6]=[#7,#16]):1]>>[#6:1]-[#6:2](=[O:5])-[O;H1].[#6:4]-[#8;H1:3]",
1083
+ "rhs_classes": [
1084
+ "carboxylates",
1085
+ "alcohols"
1086
+ ],
1087
+ "syn_smarts": "[#6;!$([#6]=[#7,#16]):101]-[#6:2](=O)-[O;H1].[#6;!$([#6]=[#6,#7,#8,#16]):102]-[#8;H1:3]>>[#6:102]-[#8;H0:3]-[#6:2](=O)-[#6:101]",
1088
+ "tags": [
1089
+ "esterification",
1090
+ "ester"
1091
+ ],
1092
+ "tier": 1
1093
+ },
1094
+ "ether-1": {
1095
+ "description": "Ullmann aryl ether synthesis: gives a biaryl ether from an aryl halide and a phenol.",
1096
+ "ld_data": {
1097
+ "display_smarts": "[#35]-[#6:201].[#8]-[#6:202]>>[#6:201]-O-[#6:202] |$;Aryl_p;;Aryl_p;Aryl_p;;Aryl_p$|"
1098
+ },
1099
+ "long_name": "Ullmann aryl ether synthesis",
1100
+ "retro_smarts": "[c;r6:1]-!@[#8;H0:3]-[c;r6:2]>>[c:1]-Cl.[c:2]-[#8;H1:3]",
1101
+ "rhs_classes": [
1102
+ "halides-aryl",
1103
+ "phenols"
1104
+ ],
1105
+ "syn_smarts": "[c;r6:101]-[Cl,Br,I].[c;r6:102]-[#8;H1:3]>>[c:101]-[#8;H0:3]-[c:102]",
1106
+ "tags": [
1107
+ "Ullmann",
1108
+ "etherification",
1109
+ "ether",
1110
+ "biaryl"
1111
+ ],
1112
+ "tier": 1
1113
+ },
1114
+ "ether-2": {
1115
+ "description": "Williamson ether synthesis: gives an ether from a primary or secondary halide and a primary, secondary or (hetero)aryl alcohol.",
1116
+ "ld_data": {
1117
+ "display_smarts": "[#6:101]-Br.[#6:102]-O>>[#6:101]-O-[#6:102]"
1118
+ },
1119
+ "long_name": "Williamson ether synthesis",
1120
+ "retro_smarts": "[#6;!$([#6](-[#6])(-[#6])-[#6]);!$(C=[C,N,O,S]):1]-[#8;H0:2]-!@[C;!$([#6](-[#6])(-[#6])-[#6]);!$(C=[C,N,O,S]);H1,H2:3]>>[C:3]-Br.[#6:1]-[#8;H1:2]",
1121
+ "rhs_classes": [
1122
+ "halides-primsec",
1123
+ "alcohols"
1124
+ ],
1125
+ "syn_smarts": "[C;!$([#6](-[#6])(-[#6])-[#6]);!H0;!$(C=[C,N,O,S]):101]-[Cl,Br].[#6;!$([#6](-[#6])(-[#6])-[#6]);!$(C=[C,N,O,S]):102]-[#8;H1:2]>>[C:101]-[#8;H0:2]-[#6:102]",
1126
+ "tags": [
1127
+ "Williamson",
1128
+ "etherification",
1129
+ "ether"
1130
+ ],
1131
+ "tier": 1
1132
+ },
1133
+ "flavone": {
1134
+ "description": "Flavone synthesis: gives a 2-aryl flavone from a 2-acyl phenol and an aryl acid chloride.",
1135
+ "ld_data": {
1136
+ "display_smarts": "[#6]-[#6](=O)-[#6]-1=[#6](-[#8])-[#6]=[#6]-[#6]=[#6]-1.Cl-[#6](-[#6:201])=O>>[#6:201]-[#6]-1=[#6]-[#6](=O)-[#6]-2=[#6](-[#8]-1)-[#6]=[#6]-[#6]=[#6]-2 |$;;;;;;;;;;;;Aryl_p;;Aryl_p;;;;;;;;;;;$|"
1137
+ },
1138
+ "long_name": "Flavone synthesis from 2-acyl phenols and aryl acid chlorides.",
1139
+ "retro_smarts": "[c:7]12[c:1][c:2][c:3][c:4][c:8]1[c:13](=[O:9])[c;H1:5][c:6](-!@[c:101])[o:12]2>>[c:7](-[O;H1:12])1[c:1][c:2][c:3][c:4][c:8](-[C:13](=[O:9])-[#6;H3:5])1.[c:101]-[C:6](=O)-Cl",
1140
+ "rhs_classes": [
1141
+ "phenols-2keto",
1142
+ "acid_chlorides-aryl"
1143
+ ],
1144
+ "syn_smarts": "[c:7](-[#8;H1:12])1[c:1][c:2][c:3][c:4][c:8](-[#6:13](=O)-[C;H3:5])1.[#6:6](=O)(-Cl)-[c:101]>>[#6:13](=O)1-[#6;H1:5]=[#6:6](-[c:101])-[#8;H0:12]-[#6:7]:2:[#6:1]:[#6:2]:[#6:3]:[#6:4]:[#6:8]-1:2",
1145
+ "tags": [
1146
+ "heterocycle formation",
1147
+ "heterocycle",
1148
+ "flavone"
1149
+ ],
1150
+ "tier": 1
1151
+ },
1152
+ "friedel-crafts-1": {
1153
+ "description": "Friedel-Crafts acylation.",
1154
+ "ld_data": {
1155
+ "display_smarts": "[#6:201]-[H].[#6:101]-C(=O)-Cl>>[#6:201]-C(=O)-[#6:101] |$Aryl_p;;;;;;Aryl_p;;$|"
1156
+ },
1157
+ "long_name": "Friedel-Crafts acylation.",
1158
+ "retro_smarts": "[c;$([c;H0]1[c;H1][c;H1][c;$([c;H1]),$(c-[#6]),$(c-[#7]),$(c-O-[#6]);!$(c-[#7](=O)=O);!$(c-C=O);!$(c-C#N);!$(c-C(F)(F)F)][c;H1][c;H1]1),$([c;H0]1[c;H1][c;$([c;H1]),$(c-[#6]),$(c-[#7]),$(c-O-[#6]);!$(c-[#7](=O)=O);!$(c-C=O);!$(c-C#N);!$(c-C(F)(F)F)][c;$([c;H1]),$(c-[#6]),$(c-[#7]),$(c-O-[#6]);!$(c-[#7](=O)=O);!$(c-C=O);!$(c-C#N);!$(c-C(F)(F)F)][a]1):101]-[C:3](=[O:4])-[#6;!$([#6]=[#6,#7,#8,#16]):102]>>[c;H1:101].[#6:102]-[C:3](=[O:4])-Cl",
1159
+ "rhs_classes": [
1160
+ "friedel-crafts_substrates",
1161
+ "acid_chlorides"
1162
+ ],
1163
+ "syn_smarts": "[c;$([c;H1]1[c;H1][c;H1][c;$([c;H1]),$(c-[#6]),$(c-[#7]),$(c-O-[#6]);!$(c-[#7](=O)=O);!$(c-C=O);!$(c-C#N);!$(c-C(F)(F)F)][c;H1][c;H1]1),$([c;H1]1[c;H1][c;$([c;H1]),$(c-[#6]),$(c-[#7]),$(c-O-[#6]);!$(c-[#7](=O)=O);!$(c-C=O);!$(c-C#N);!$(c-C(F)(F)F)][c;$([c;H1]),$(c-[#6]),$(c-[#7]),$(c-O-[#6]);!$(c-[#7](=O)=O);!$(c-C=O);!$(c-C#N);!$(c-C(F)(F)F)][a]1):101].[#6;!$([#6]=[#6,#7,#8,#16]):102]-[C:3](=[O:4])-Cl>>[c;H0:101]-[C:3](=[O:4])-[#6:102]",
1164
+ "tags": [
1165
+ "Friedel-Crafts",
1166
+ "acylation"
1167
+ ],
1168
+ "tier": 1
1169
+ },
1170
+ "furan-1": {
1171
+ "description": "Feist-Benary furan synthesis from a beta-keto-ester and a 2-halo ketone.",
1172
+ "ld_data": {
1173
+ "display_smarts": "[#6:101]-O-[#6](=O)-[#6]-[#6](=O)-[#6:102].[#6:103]-[#6](=O)-[#6](-[#6:104])-[#35]>>[#6:101]-O-[#6](=O)-[#6]=1-[#6](-[#6:103])=[#6](-[#6:104])-[#8]-[#6](-[#6:102])=1"
1174
+ },
1175
+ "long_name": "Feist-Benary furan synthesis from 1,3-diketones and 2-halo ketones.",
1176
+ "retro_smarts": "[#6:103]-[#8:6]-[#6:3](=[O:7])-[#6:4]1:[#6;R1:1](-[C:101]):[#6;$([#6;H0]-[#6;$(c),$([C;!H0])]),$([#6;H1]);R1:2]:[o:8]:[#6:5](-[#6:104]):1>>[#6:103]-[#8:6]-[#6:3](=[O:7])-[#6;H2:4]-[#6:5](=[O:8])-[#6:104].[C:101]-[#6:1](=O)-[#6:2]-[#35]",
1177
+ "rhs_classes": [
1178
+ "esters-3keto",
1179
+ "ketones-2halo-aliphatic"
1180
+ ],
1181
+ "syn_smarts": "[#6:101]!@[O:5]-[#6:2](=O)-[#6;H2:3]-[#6:4](=O)-[#6:102].[C:103]-[#6;R0;!r3;!r4:7](=O)-[#6;$([#6;H2]),$([#6;H1](-[#6]=O)-[#6;$(c),$([C;!H0])]);R0:8]-[#17,#35,#53]>>[#6:101]-[O:5]-[#6:2](=O)-[#6;H0:3]1-[#6:7](-[C:103])=[#6:8]-[#8]-[#6:4](-[#6:102])=1",
1182
+ "tags": [
1183
+ "Feist-Benary",
1184
+ "heterocycle formation",
1185
+ "heterocycle",
1186
+ "furan"
1187
+ ],
1188
+ "tier": 1
1189
+ },
1190
+ "goldberg-1": {
1191
+ "description": "Goldberg reaction: Ullman condensation of an aryl halide with an aniline or acetanilide.",
1192
+ "ld_data": {
1193
+ "display_smarts": "[#35]-[#6:201].[#7]-[#6:202]>>[#6:201]-N-[#6:202] |$;Aryl_p;;Aryl_p;Aryl_p;;Aryl_p$|"
1194
+ },
1195
+ "long_name": "Goldberg reaction of an aryl halide with an aniline or acetanilide.",
1196
+ "retro_smarts": "[c;r6:1]-!@[N;$([N;H1]),$([#7;H0](-[C,c])(-[c;r6:1])-[c;r6:2]):3]-[c;r6:2]>>[c:1]-Br.[c:2]-[N:3]",
1197
+ "rhs_classes": [
1198
+ "halides-aryl",
1199
+ "anilines-goldberg"
1200
+ ],
1201
+ "syn_smarts": "[c;r6:101]-[Cl,Br,I].[c;r6:102]-[N;$([N;H2]),$([N;H1](-[C,c])-[c;r6:102]),$([N;H1](-C(=O)[#6])-[c;r6:102]):3]>>[c:101]-[N:3]-[c:102]",
1202
+ "tags": [
1203
+ "Goldberg",
1204
+ "Ullman",
1205
+ "condensation",
1206
+ "diaryl amine"
1207
+ ],
1208
+ "tier": 1
1209
+ },
1210
+ "goldberg-2": {
1211
+ "description": "Goldberg reaction: Ullman condensation of an aryl halide with a benzylpyrazolone.",
1212
+ "ld_data": {
1213
+ "display_smarts": "[#35]-[#6:201].C=1-2-C=C-C=C-C=1-N-N(-[#6:101])-C(=O)-2>>C=1-2-C=C-C=C-C=1-N(-[#6:201])-N(-[#6:101])-C(=O)-2 |$;Aryl_p;;;;;;;;;;;;;;;;;;;Aryl_p;;;$|"
1214
+ },
1215
+ "long_name": "Goldberg reaction of an aryl halide with a benzylpyrazolone.",
1216
+ "retro_smarts": "[c;r6:1]-!@[n:3]1[n;H0:4][c:5](=[O:7])[c:6][c:2]1>>[c:1]-Br.[n;H1:3]1[n;H0:4][c:5](=[O:7])[c:6][c:2]1",
1217
+ "rhs_classes": [
1218
+ "halides-aryl",
1219
+ "pyrazolones"
1220
+ ],
1221
+ "syn_smarts": "[c;r6:101]-[Cl,Br,I].[n;H1:3]1[n;H0:4][c:5](=O)[c:6][c:2]1>>[c;r6:101]-[n;H0:3]1[n;H0:4][c:5](=O)[c:6][c:2]1",
1222
+ "tags": [
1223
+ "Goldberg",
1224
+ "Ullman",
1225
+ "condensation",
1226
+ "diaryl amine"
1227
+ ],
1228
+ "tier": 1
1229
+ },
1230
+ "heck": {
1231
+ "allow_multiple_products": true,
1232
+ "description": "Heck reaction: coupling of an activated alkene and aryl or vinyl halides.",
1233
+ "ld_data": {
1234
+ "display_smarts": "[#6:101]-[Br].[#6:102]-C=[#6]>>[#6:102]/C=C/[#6:101]"
1235
+ },
1236
+ "long_name": "Heck reaction",
1237
+ "retro_smarts": "[#6;$([#6]=[#6]),$(c):4]/!@[C;$([C;H1]-[#6;$([#6]=[#6]),$(c):4]),$([C;H0](-[#6;$(c),$([C;!H0])])-[#6;$([#6]=[#6]),$(c):4]):1]=[C;$([C;H1]-[#6;$(c),$(C(=O)O),$(C#N):3]),$([C;H0](-[#6;$(c),$([C;!H0])])-[#6;$(c),$(C(=O)O),$(C#N):3]):2]/[#6;$(c),$(C(=O)O),$(C#N):3]>>[#6:4]-Br.[#6:3]-[#6:2]=[#6:1]",
1238
+ "rhs_classes": [
1239
+ "halides-aryl-vinyl",
1240
+ "alkenes-disub"
1241
+ ],
1242
+ "syn_smarts": "[#6;$([#6]=[#6]),$(c):101]-[Cl,Br,I].[#6;$(c),$(C(=O)O),$(C#N):102]-[C;$([C;H1]-[#6;$(c),$(C(=O)O),$(C#N):102]),$([C;H0](-[#6;$(c),$([C;!H0])])-[#6;$(c),$(C(=O)O),$(C#N):102]):2]=[C;$([C;H1]-[#6;$(c),$([C;!H0]):4]),$([C;H2]):1]>>[#6:101]/[C:1]=[C:2]/[#6:102]",
1243
+ "tags": [
1244
+ "Heck",
1245
+ "C-C bond formation",
1246
+ "C-C"
1247
+ ],
1248
+ "tier": 1
1249
+ },
1250
+ "imidazole-1": {
1251
+ "description": "Imidazole synthesis from an alpha-chloro aldehyde and an amidine.",
1252
+ "ld_data": {
1253
+ "display_smarts": "[Cl]-[#6](-[#6:101])-[#6]=O.[#7]-[#6](-[#6:102])=[#7]>>[#6]-1=[#6](-[#6:101])-[#7]=[#6](-[#6:102])-[#7]-1"
1254
+ },
1255
+ "long_name": "Synthesis of 2-substituted imidazoles",
1256
+ "retro_smarts": "[#6;H1:4]1:[#6:5]:[#7;D2:3]:[#6;$([#6;H1]),$([#6;H0]-[#6,#7:101]):2]:[#7;D2:1]:1>>Br-[#6:5]-[#6;H1:4]=O.[#7:3]-[#6:2]=[#7:1]",
1257
+ "rhs_classes": [
1258
+ "aldehydes-2halo",
1259
+ "amidines"
1260
+ ],
1261
+ "syn_smarts": "[Cl,Br]-[#6;H1,H2:5]-[#6;H1:4]=O.[#7;H2:3]-[#6;$([#6;H1]),$([#6;H0](-[#7;H2:3])-[#6,#7:101]):2]=[#7;H1:1]>>[#6:4]1=[#6:5]-[#7:3]=[#6;$([#6;H1]),$([#6;H0]-[#6:101]):2]-[#7:1]-1",
1262
+ "tags": [
1263
+ "heterocycle formation",
1264
+ "heterocycle",
1265
+ "imidazole"
1266
+ ],
1267
+ "tier": 1
1268
+ },
1269
+ "imidazole-2": {
1270
+ "description": "Imidazole synthesis from an aryl aldehyde, 2-halo ketone and a primary amine.",
1271
+ "ld_data": {
1272
+ "display_smarts": "[#6:201]-[#6]=O.[#35]-[#6]-[#6](-[#6:202])=O.[#6:101]-[#7]>>[#6:101]-[#7]-1-[#6]=[#6](-[#6:202])-[#7]=[#6]-1-[#6:201] |$Aryl_p;;;;;;Aryl_p;;;;;;;;Aryl_p;;;Aryl_p$|"
1273
+ },
1274
+ "long_name": "Synthesis of 1,2,4-substituted imidazoles",
1275
+ "retro_smarts": "[c:1]1(-!@[c:7])[n:8](-!@[#6;!$([#6]=[#6,#7,#8,#16]):9])[c;$([c;H1]),$([c;H0]-[#6;$(c),$([C;!H0])]):5][c:6](-[c:3])n1>>[c:7]-[#6;H1:1]=O.[C:5](-[Cl])-[C:6](=O)-[c:3].[#7:8]-[#6:9]",
1276
+ "rhs_classes": [
1277
+ "aldehydes-aryl",
1278
+ "ketones-aryl-2halo",
1279
+ "amines-prim"
1280
+ ],
1281
+ "syn_smarts": "[c:101]-[#6;H1:1]=O.[#6;$([#6;H2]),$([#6;H1](-[#6:6]=O)-[#6;$(c),$([C;!H0])]):5](-[Cl,Br])-[#6:6](=O)-[c:102].[#7;H2:8]-[#6;!$([#6]=[#6,#7,#8,#16]):103]>>[#6:101]-[#6;H0:1]1-[#7;H0:8](-[#6:103])-[#6:5]=[#6:6](-[#6:102])-[#7]=1",
1282
+ "tags": [
1283
+ "heterocycle formation",
1284
+ "heterocycle",
1285
+ "imidazole"
1286
+ ],
1287
+ "tier": 1
1288
+ },
1289
+ "imidazole-3": {
1290
+ "description": "Synthesis of triaryl-imidazoles.",
1291
+ "ld_data": {
1292
+ "display_smarts": "[#6:201]-C(=O)-C(=O)-[#6:202].[#6:203]-[#6]=O>>[#6:201]-C-1=C(-[#6:202])-N=C(-[#6:203])-N-1 |$Aryl_p;;;;;Aryl_p;Aryl_p;;;Aryl_p;;;Aryl_p;;;Aryl_p;$|"
1293
+ },
1294
+ "long_name": "Synthesis of triaryl-imidazoles",
1295
+ "retro_smarts": "[c:101]-[c:2]1[c:3](-[c:102])n[c:4](-!@[c:103])n1>>[c:101]-[C:2](=O)-[C:3](=O)-[c:102].[c:103]-[C;H1:4]=O",
1296
+ "rhs_classes": [
1297
+ "diketones-diaryl",
1298
+ "aldehydes-aryl"
1299
+ ],
1300
+ "syn_smarts": "[c:101]-[C:2](~O)-!@[C;H0:3](=O)-[c:102].[c:103]-[C;H1:4]=O>>[c:101]-[C;H0:2]1=[C;H0:3](-[c:102])-N=[C;H0:4](-[c:103])-N-1",
1301
+ "tags": [
1302
+ "heterocycle formation",
1303
+ "heterocycle",
1304
+ "imidazole"
1305
+ ],
1306
+ "tier": 1
1307
+ },
1308
+ "indole-1": {
1309
+ "allow_multiple_products": true,
1310
+ "description": "Bischler-Mohlau indole synthesis: gives a 2-aryl Indole from an aniline and a 2-halo aryl ketone.",
1311
+ "ld_data": {
1312
+ "display_smarts": "[#35]-[#6]-[#6](-[#6:201])=O.[#7]-[#6]-1=[#6]-[#6]=[#6]-[#6]=[#6]-1>>[#6:201]-[#6]-1=[#6]-[#6]-2=[#6](-[#7]-1)-[#6]=[#6]-[#6]=[#6]-2 |$;;;Aryl_p;;;;;;;;;Aryl_p;;;;;;;;;$|"
1313
+ },
1314
+ "long_name": "Bischler-Mohlau indole synthesis",
1315
+ "retro_smarts": "[#6;H1:3]1:[#6:2](-!@[c:12]):[#7;D2:4]:[c:5]2:[c:6]:[c:7]:[c:8]:[c:9]:[c:1]:1:2>>Cl-[#6:2]-[#6:3](=O)-[c:12].[#7:4]-[c:5]1[c;H1:1][c:9][c:8][c:7][c:6]1",
1316
+ "rhs_classes": [
1317
+ "ketones-aryl-2halo",
1318
+ "anilines-2H"
1319
+ ],
1320
+ "syn_smarts": "[Cl,Br,I]-[#6;H2:2]-[#6:3](=O)-[c:101].[#7;H2:4]-[c:5]1[c;H1:1][c:9][c:8][c:7][c:6]1>>[#6:3]1=[C;H0:2](-[c:101])-[#7;H1:4]-[c:5]2[c:6][c:7][c:8][c:9][c;H0:1]-12",
1321
+ "tags": [
1322
+ "Bischler-Mohlau",
1323
+ "heterocycle formation",
1324
+ "heterocycle",
1325
+ "indole"
1326
+ ],
1327
+ "tier": 1
1328
+ },
1329
+ "indole-2": {
1330
+ "allow_multiple_products": true,
1331
+ "description": "Fischer indole: gives an indole from an aryl hydrazine and a ketone.",
1332
+ "ld_data": {
1333
+ "display_smarts": "[#6]=1-[#6]=[#6]-[#6]=[#6]-[#6]=1-[#7]-[#7].[#6:101]-[#6:9]-[#6](=O)-[#6:102]>>[#6]=1-2-[#6]=[#6]-[#6]=[#6]-[#6]=1-[#7]-[#6](-[#6:102])=[#6](-[#6:101])-2"
1334
+ },
1335
+ "long_name": "Fischer indole synthesis",
1336
+ "retro_smarts": "[#6:1]:1:2:[#6:2]:[#6:3]:[#6:4]:[#6:5]:[#6:6]:1:[#7;D2:7]:[#6;!r4;!r3:10](-[#6;!$(C=[C,N,O,S]):11]):[#6:9](-[#6;!$(C=[C,N,O,S]):8]):2>>[c:1]1[c:2][c:3][c:4][c:5][c:6]1-[#7;H1:7]-[N;H2].[#6:8]-[#6;H2:9]-[#6:10](=O)-[#6:11]",
1337
+ "rhs_classes": [
1338
+ "hydrazines-aryl",
1339
+ "ketones-2unsub"
1340
+ ],
1341
+ "syn_smarts": "[c;H1:1]1[c:2][c:3][c:4][c:5][c:6]1-[#7;H1:7]-[N;H2].[#6;!$(C=[C,N,O,S]):102]-[#6;H2:9]-[#6;!r4;!r3:10](=O)-[#6;!$(C=[C,N,O,S]):101]>>[c;H0:1]12[c:2][c:3][c:4][c:5][c:6]1[N:7][C:10](-[#6:101])=[C;H0:9](-[#6:102])2",
1342
+ "tags": [
1343
+ "Fischer",
1344
+ "heterocycle formation",
1345
+ "heterocycle",
1346
+ "indole"
1347
+ ],
1348
+ "tier": 1
1349
+ },
1350
+ "isocyanate-1": {
1351
+ "description": "Isocyanate formation from primary amines.",
1352
+ "ld_data": {
1353
+ "display_smarts": "[#6:101]-[#7]>>[#6:101]-[#7]=[#6]=[#8]"
1354
+ },
1355
+ "long_name": "Isocyanate formation from primary amines.",
1356
+ "retro_smarts": "[#6;!$([#6]=[#7,#8,#16]):101]-[N:2]=C=O>>[#6:101]-[N;H2:2]",
1357
+ "rhs_classes": [
1358
+ "amines-prim"
1359
+ ],
1360
+ "syn_smarts": "[#6;!$([#6]=[#7,#8,#16]):101]-[N;H2:2]>>[#6:101]-[N;H0:2]=C=O",
1361
+ "tags": [
1362
+ "isocyanate",
1363
+ "transformation"
1364
+ ],
1365
+ "tier": 1
1366
+ },
1367
+ "isoxazole-1": {
1368
+ "description": "Claisen isoxazole synthesis from a beta-ketoester and hydroxylamine.",
1369
+ "ld_data": {
1370
+ "display_smarts": "[#6:101]-[#6](=O)-[#6](-[#6:102])-[#6](=O)-O-C>>[#6:101]-C=1-O-N=C(-O)-C(-[#6:102])=1"
1371
+ },
1372
+ "long_name": "Claisen isoxazole synthesis",
1373
+ "retro_smarts": "[#6:101]-[c:1]1on[c:3](-[O;H1:4])[c;$([c;H1]),$([c;H0]-[C;!H0:102]):2]1>>[#6:101]-[C:1](=O)-[C:2]-[C:3](=[O;H0:4])-OC",
1374
+ "rhs_classes": [
1375
+ "esters-3keto"
1376
+ ],
1377
+ "syn_smarts": "[#6:101]-[C:1](=O)-[C;$([C;H2]),$([C;H1](-C=O)(-C=O)-[C;!H0;!$(C=N)]):2]-[C:3](=O)-[O;!R]-[#6]>>[#6:101]-[c:1]1on[c:3](-[O;H1])[c:2]1",
1378
+ "tags": [
1379
+ "Claisen",
1380
+ "heterocycle formation",
1381
+ "heterocycle",
1382
+ "transformation"
1383
+ ],
1384
+ "tier": 1
1385
+ },
1386
+ "mitsunobu-1": {
1387
+ "description": "Mitsunobu: gives an aryl ether from an alcohol and a phenol.",
1388
+ "ld_data": {
1389
+ "display_smarts": "[#6:101]-[#8].[#8]-[#6:201]>>[#6:201]-[#8]-[#6:101] |$;;;Aryl_p;;;Aryl_p$|"
1390
+ },
1391
+ "long_name": "Mitsunobu (alcohol)",
1392
+ "retro_smarts": "[C;$([C;H1](-[#6;$(c),$([C;!H0])])-[#6;$(c),$([C;!H0])]),$([C;H2]-[#6;$(c),$([C;!H0])]),$([C;H3]);!$(C=[C,N,O,S]):101]-!@[O:2]-[c:102]>>[C:101]-O.[O:2]-[c:102]",
1393
+ "rhs_classes": [
1394
+ "alcohols-primsec",
1395
+ "phenols-2H"
1396
+ ],
1397
+ "syn_smarts": "[C;$([C;H1](-[#6;$(c),$([C;!H0])])-[#6;$(c),$([C;!H0])]),$([C;H2]-[#6;$(c),$([C;!H0])]),$([C;H3]);!$(C=[C,N,O,S]):101]-[O;H1].[O;H1:2]-[c:102]>>[C:101]-[O;H0:2]-[c:102]",
1398
+ "tags": [
1399
+ "Mitsunobu",
1400
+ "etherification",
1401
+ "ether"
1402
+ ],
1403
+ "tier": 1
1404
+ },
1405
+ "mitsunobu-2": {
1406
+ "description": "Mitsunobu: alkylation of a sulfonamide with a primary or secondary alcohol.",
1407
+ "ld_data": {
1408
+ "display_smarts": "[#6:101]-O.[#7](-S(=O)(=O)-[#6:102])-[#6:103]>>[#6:101]-[#7](-S(=O)(=O)-[#6:102])-[#6:103]"
1409
+ },
1410
+ "long_name": "Mitsunobu (sulfonamide)",
1411
+ "retro_smarts": "[C;$([C;H1](-[#6;$(c),$([C;!H0])])-[#6;$(c),$([C;!H0])]),$([C;H2]-[#6;$(c),$([C;!H0])]),$([C;H3]);!$(C=[C,N,O,S]):101]-!@[#7;$([N;H1]),$([N;H0](-[#6;!$(C=[C,N,O,S]):103])-[#6;!$(C=[C,N,O,S]):102]):2]-[S:3](=[O:4])(=[O:5])-[#6;!$(C=[C,N,O,S]):102]>>[#6:101]-O.[#7;$([N;H2]),$([N;H1]-[#6;!$(C=[C,N,O,S]):103]):2]-[S:3](=[O:4])(=[O:5])-[#6:102]",
1412
+ "rhs_classes": [
1413
+ "alcohols-primsec",
1414
+ "sulfonamides-primsec"
1415
+ ],
1416
+ "syn_smarts": "[C;$([C;H1](-[#6;$(c),$([C;!H0])])-[#6;$(c),$([C;!H0])]),$([C;H2]-[#6;$(c),$([C;!H0])]),$([C;H3]);!$(C=[C,N,O,S]):101]-[O;H1].[#7;$([N;H2]),$([N;H1]-[#6;!$(C=[C,N,O,S]):103]):2]-[S:3](=O)(=O)-[#6;!$(C=[C,N,O,S]):102]>>[#6:101]-[#7;$([N;H1]),$([N;H0](-[#6:103])-[#6:102]):2]-[S:3](=O)(=O)-[#6:102]",
1417
+ "tags": [
1418
+ "Mitsunobu",
1419
+ "alkylation",
1420
+ "sulfonamide"
1421
+ ],
1422
+ "tier": 1
1423
+ },
1424
+ "mitsunobu-3": {
1425
+ "description": "Mitsunobu: N-alkylation of a tetrazole with a primary or secondary alcohol.",
1426
+ "ld_data": {
1427
+ "display_smarts": "[#6:101]-O.[#7]-1-[#7]=[#7]-[#6]=[#7]-1>>[#6:101]-[#7]-1-[#7]=[#7]-[#6]=[#7]-1"
1428
+ },
1429
+ "long_name": "Mitsunobu (2-substituted tetrazole)",
1430
+ "retro_smarts": "[C;$([C;H1](-[#6;$(c),$([C;!H0])])-[#6;$(c),$([C;!H0])]),$([C;H2]-[#6;$(c),$([C;!H0])]),$([C;H3]);!$(C=[C,N,O,S]):1]-!@[n:4]1[n:5][c:6][n:2][n:3]1>>[C:1]-O.[n:2]1[n:3][n;H1:4][n:5][c:6]1",
1431
+ "rhs_classes": [
1432
+ "alcohols-primsec",
1433
+ "tetrazoles-2H"
1434
+ ],
1435
+ "syn_smarts": "[C;$([C;H1](-[#6;$(c),$([C;!H0])])-[#6;$(c),$([C;!H0])]),$([C;H2]-[#6;$(c),$([C;!H0])]),$([C;H3]);!$(C=[C,N,O,S]):101]-[O;H1].[nH:4]1[n:3][n:2][c:6][n:5]1>>[#6:101]-[#7;H0:4]1-[#7:3]=[#7:2]-[#6:6]=[#7:5]-1",
1436
+ "tags": [
1437
+ "Mitsunobu",
1438
+ "alkylation",
1439
+ "tetrazole"
1440
+ ],
1441
+ "tier": 1
1442
+ },
1443
+ "mitsunobu-4": {
1444
+ "description": "Mitsunobu: N-alkylation of a tetrazole with a primary or secondary alcohol.",
1445
+ "ld_data": {
1446
+ "display_smarts": "[#6:101]-O.[#7]-1=[#7]-[#7]=[#6]-[#7]-1>>[#6:101]-[#7]-1-[#7]=[#7]-[#7]=[#6]-1"
1447
+ },
1448
+ "long_name": "Mitsunobu (1-substituted tetrazole)",
1449
+ "retro_smarts": "[C;$([C;H1](-[#6;$(c),$([C;!H0])])-[#6;$(c),$([C;!H0])]),$([C;H2]-[#6;$(c),$([C;!H0])]),$([C;H3]);!$(C=[C,N,O,S]):1]-!@[n:2]1[n:3][n:4][n:5][c:6]1>>[C:1]-O.[n;H1:2]1[n:3][n:4][n:5][c:6]1",
1450
+ "rhs_classes": [
1451
+ "alcohols-primsec",
1452
+ "tetrazoles-1H"
1453
+ ],
1454
+ "syn_smarts": "[C;$([C;H1](-[#6;$(c),$([C;!H0])])-[#6;$(c),$([C;!H0])]),$([C;H2]-[#6;$(c),$([C;!H0])]),$([C;H3]);!$(C=[C,N,O,S]):101]-[O;H1].[n;H1:2]1[n:3][n:4][n:5][c:6]1>>[C:101]-[n;H0:2]1[n:3][n:4][n:5][c:6]1",
1455
+ "tags": [
1456
+ "Mitsunobu",
1457
+ "alkylation",
1458
+ "tetrazole"
1459
+ ],
1460
+ "tier": 1
1461
+ },
1462
+ "mitsunobu-5": {
1463
+ "description": "Mitsunobu: esterification from an alcohol and a carboxylic acid.",
1464
+ "ld_data": {
1465
+ "display_smarts": "[#6:101]-O.[#6](=O)(-O)-[#6:102]>>[#6:101]-O-C(=O)-[#6:102]"
1466
+ },
1467
+ "long_name": "Mitsunobu (ester)",
1468
+ "retro_smarts": "[C;$([C;H1](-[#6;$(c),$([C;!H0])])-[#6;$(c),$([C;!H0])]),$([C;H2]-[#6;$(c),$([C;!H0])]),$([C;H3]);!$(C=[C,N,O,S]):1]-[#8:2]-!@[#6:3](=[O:5])-[#6;!$(C=[C,N,O,S]):4]>>[#6:1]-[#8:2].[#6:3](=[O:5])(-[O;H1])-[#6:4]",
1469
+ "rhs_classes": [
1470
+ "alcohols-primsec",
1471
+ "carboxylates"
1472
+ ],
1473
+ "syn_smarts": "[C;$([C;H1](-[#6;$(c),$([C;!H0])])-[#6;$(c),$([C;!H0])]),$([C;H2]-[#6;$(c),$([C;!H0])]),$([C;H3]);!$(C=[C,N,O,S]):101]-[O;H1:2].[O;H1]-[#6:3](=[O:4])-[#6;!$(C=[C,N,O,S]):102]>>[#6:101]-[#8;H0:2]-[#6:3](=[O:4])-[#6:102]",
1474
+ "tags": [
1475
+ "Mitsunobu",
1476
+ "esterification",
1477
+ "ester"
1478
+ ],
1479
+ "tier": 1
1480
+ },
1481
+ "miyaura-borylation": {
1482
+ "description": "Miyaura borylation.",
1483
+ "ld_data": {
1484
+ "display_smarts": "[#35]-[#6:201]>>[#6:201]-B-1-O-C(-[#6])(-[#6])-C(-[#6])(-[#6])-O-1 |$;Aryl_p;Aryl_p;;;|"
1485
+ },
1486
+ "long_name": "Miyaura borylation",
1487
+ "retro_smarts": "[#6;!R2;$(c),$(C=C):101]-!@B(-O)O>>[#6:101]-[#35]",
1488
+ "rhs_classes": [
1489
+ "halides-aryl-vinyl"
1490
+ ],
1491
+ "syn_smarts": "[#6;$(c),$(C=C):101]-[#35,#53]>>[#6:101]-B1OC(-C)(-C)C(-C)(-C)O1",
1492
+ "tags": [
1493
+ "Miyaura",
1494
+ "borylation",
1495
+ "boronic ester",
1496
+ "boronate",
1497
+ "transformation"
1498
+ ],
1499
+ "tier": 1
1500
+ },
1501
+ "negishi": {
1502
+ "description": "Negishi: aryl C-C coupling from two halides (one will be prepared as an organozinc).",
1503
+ "ld_data": {
1504
+ "display_smarts": "Cl-[#6:201].[#6:202]-Cl>>[#6:201]-[#6:202] |$;Aryl_p;Aryl_p;;Aryl_p;Aryl_p$|"
1505
+ },
1506
+ "long_name": "Negishi Coupling",
1507
+ "retro_smarts": "[#6;!R2;$(c),$(C=C),$(C#C);!$([#6]~[S,N,O,P]):2]-!@[#6;!R2;$(c),$(C=C);!$([#6]~[S,N,O,P]):1]>>[#6:2]-Cl.Cl-[#6:1]",
1508
+ "rhs_classes": [
1509
+ "halides-aryl-vinyl-alkynyl",
1510
+ "halides-aryl-vinyl"
1511
+ ],
1512
+ "syn_smarts": "[#6;$(c),$(C=C),$(C#C);!$([#6]~[S,N,O,P]):101]-[Cl,Br,I].[#6;$(c),$(C=C);!$([#6]~[S,N,O,P]):102]-[Cl,Br,I]>>[#6:101]-[#6:102]",
1513
+ "tags": [
1514
+ "Negishi",
1515
+ "C-C bond formation",
1516
+ "C-C"
1517
+ ],
1518
+ "tier": 1
1519
+ },
1520
+ "oxadiazole-1": {
1521
+ "description": "Oxadiazole synthesis from a nitrile (converted to an amidoxime) and a carboxylic acid.",
1522
+ "ld_data": {
1523
+ "display_smarts": "[#6:101]-[#6]#[#7].[#6:102]-C(=O)-O>>[#6:101]-[#6]-1=N-O-C(-[#6:102])=N-1"
1524
+ },
1525
+ "long_name": "Oxadiazole synthesis",
1526
+ "retro_smarts": "[#6;!$(C=[C,N,O,S]):101]-!@[c:2]1[n:3][o:5][c:4](-!@[#6;!$(C=[C,N,O,S]):102])n1>>[#6:101]-[#6:2]#[#7:3].[#6:102]-[C:4](=O)-[O;H1:5]",
1527
+ "rhs_classes": [
1528
+ "nitriles",
1529
+ "carboxylates"
1530
+ ],
1531
+ "syn_smarts": "[#6;!$(C=[C,N,O,S]):101]-[#6:2]#[#7:3].[#6;!$(C=[C,N,O,S]):102]-[C:4](=O)-[O;H1]>>[#6:101]-[#6:2]1=[#7:3]-O-[C:4](-[#6:102])=N-1",
1532
+ "tags": [
1533
+ "heterocycle formation",
1534
+ "heterocycle",
1535
+ "oxadiazole"
1536
+ ],
1537
+ "tier": 1
1538
+ },
1539
+ "oxazole-1": {
1540
+ "description": "Fischer Oxazole Synthesis: Generates an oxazole from an aldehyde and a cyanohydrin.",
1541
+ "ld_data": {
1542
+ "display_smarts": "[#6:101]-C=O.N#C-C(-O)-[#6:102]>>C=1(-[#6:101])-O-C(-[#6:102])=C-N=1"
1543
+ },
1544
+ "long_name": "Fischer oxazole synthesis",
1545
+ "retro_smarts": "[#6:1]1(-!@[#6;!$(C=[C,N,O,S]):6]):[#8:2]:[#6:3](-!@[#6;!$(C=[C,N,O,S]):7]):[#6:5]:[#7:4]:1>>[#6:6]-[#6;H1:1]=[#8:2].[#7:4]#[#6:5]-[#6:3](-O)-[#6:7]",
1546
+ "rhs_classes": [
1547
+ "aldehydes",
1548
+ "cyanohydrins"
1549
+ ],
1550
+ "syn_smarts": "[#6;!$(C=[C,N,O,S]):101]-[#6;H1:1]=O.[#7:4]#[#6:5]-[#6:3](-[#8;$([O;H1]):2])-[#6;!$(C=[C,N,O,S]):102]>>[#6;H0:1]1(-[#6:101])-[#8;H0:2]-[#6:3](-[#6:102])=[#6:5]-[#7:4]=1",
1551
+ "tags": [
1552
+ "Fischer",
1553
+ "heterocycle formation",
1554
+ "heterocycle",
1555
+ "oxazole"
1556
+ ],
1557
+ "tier": 1
1558
+ },
1559
+ "oxazole-2": {
1560
+ "description": "2,4-Disubstituted oxazole synthesis from monosubstituted alkynes and acetonitrile or proprionitrile (PhIO as oxygen source).",
1561
+ "ld_data": {
1562
+ "display_smarts": "[#6:101]-C#C.N#C-[#6:102]>>[#6:101]-C-1=C-O-C(-[#6:102])=N-1"
1563
+ },
1564
+ "long_name": "2,4-Disubstituted oxazole synthesis",
1565
+ "retro_smarts": "[#6;!$(C=[C,N,O,S]):1]-!@[#6:2]1:[#6;H1:3]:[#8]:[#6:5](-!@[C;$([C;H3]),$([C;H2]-[C;H3]):6]):[#7:4]:1>>[#6:1]-[#6:2]#[#6:3].[#7:4]#[#6:5]-[C:6]",
1566
+ "rhs_classes": [
1567
+ "alkynes-monosub",
1568
+ "nitriles-oxazoles"
1569
+ ],
1570
+ "syn_smarts": "[#6;!$(C=[C,N,O,S]):101]-[#6:2]#[#6;H1:3].[#7:4]#[#6:5]-[C;$([C;H3]),$([C;H2]-[C;H3]):102]>>[#6:101]-[#6:2]1=[#6:3]-[#8]-[#6:5](-[C:102])=[#7:4]-1",
1571
+ "tags": [
1572
+ "heterocycle formation",
1573
+ "heterocycle",
1574
+ "oxazole"
1575
+ ],
1576
+ "tier": 1
1577
+ },
1578
+ "phthalazinone": {
1579
+ "description": "Phthalazinone synthesis from 2-acylbenzoic acid and a hydrazine.",
1580
+ "ld_data": {
1581
+ "display_smarts": "[#6:101]-C(=O)-C=2-C=C-C=C-C=2-C(=O)-O.[#7]-N-[#6:102]>>[#6:101]-C=1-C=2-C=C-C=C-C=2-C(=O)-N(-[#6:102])-N=1"
1582
+ },
1583
+ "long_name": "Phthalazinone synthesis",
1584
+ "retro_smarts": "[#6;!$(C=[C,N,O,S]):101]-!@[#6:2]1[c;!$(c-[C,N]);R2:3][c;!$(c-[C,N]);R2:4][#6:5](=[O:8])[#7:7](-!@[#6;!$([#6]=[#6,#7,#8,#16]):102])[#7:6]1>>[#6:101]-[C:2](=O)-[c:3][c:4]-[C:5](=[O:8])-O.[#7;H2:6]-[#7;H1:7]-[#6:102]",
1585
+ "rhs_classes": [
1586
+ "benzoicacids-2acyl",
1587
+ "hydrazines"
1588
+ ],
1589
+ "syn_smarts": "[#6;!$(C-[#17,#35,#53]);!$(C=[C,N,O,S]):101]!@-[C:2](=O)-[c:3][c:4]-[C:5](=O)-[O;H1].[#7;H2:6]-[#7;H1:7]-[#6;!$([#6]=[#6,#7,#8,#16]):102]>>[#6:101]-[C:2]2-[c:3][c:4]-[C:5](=O)-[#7;H0:7](-[#6:102])-[#7;H0:6]=2",
1590
+ "tags": [
1591
+ "heterocycle formation",
1592
+ "heterocycle",
1593
+ "phthalazinone"
1594
+ ],
1595
+ "tier": 1
1596
+ },
1597
+ "pictet-spengler": {
1598
+ "allow_multiple_products": true,
1599
+ "description": "Pictet-Spengler reaction.",
1600
+ "ld_data": {
1601
+ "display_smarts": "C=1-C=C-C=C-C=1-C-C-[#7].[#6:101]-[#6](=O)>>C=1-2-C=C-C=C-C=1-C-C-[#7]-C(-[#6:101])-2"
1602
+ },
1603
+ "long_name": "Pictet-Spengler cyclization",
1604
+ "retro_smarts": "[c;R2:1]1:[c;R2:2]-[C!H0:3]-[C;!H0:4]-[N;H1:5]-[#6:6](-!@[#6:7])-1>>[#6:1]:[#6:2]-[C:3]-[C:4]-[N:5].[#6:7]-[#6;H1:6]=O",
1605
+ "rhs_classes": [
1606
+ "amines-arylethyl",
1607
+ "aldehydes"
1608
+ ],
1609
+ "syn_smarts": "[c;H1:1][c:2]-[C;!R;!H0:3]-[C;!H0:4]-[N;H2:5].[#6:7]-[C;H1:6](=O)>>[c;R2;H0:1]1:[c;R2:2]-[C:3]-[C:4]-[N;H1:5]-[#6:6](-[#6:7])-1",
1610
+ "tags": [
1611
+ "Pictet-Spengler",
1612
+ "heterocycle formation",
1613
+ "heterocycle"
1614
+ ],
1615
+ "tier": 1
1616
+ },
1617
+ "pomeranz-fritsch": {
1618
+ "allow_multiple_products": true,
1619
+ "description": "Pomeranz-Fritsch synthesis of isoquinolines.",
1620
+ "ld_data": {
1621
+ "display_smarts": "C=1-C=C-C=C-C=1-C(=O)-[#6:101]>>[#6:101]-C-1=N-C=C-C-2=C-1-C=C-C=C-2"
1622
+ },
1623
+ "long_name": "Pomeranz-Fritsch synthesis of isoquinolines",
1624
+ "retro_smarts": "[c:1]12[c;$([c;H1]),$(c(c)(c)-[#6]),$(c-[#17,#35]),$(c-O-[#6]);!$(c-C=O);!$(c-C#N);!$(c-C(F)(F)F):4][c;$([c;H1]),$(c(c)(c)-[#6]),$(c-[#17,#35]),$(c-O-[#6]);!$(c-C=O);!$(c-C#N);!$(c-C(F)(F)F):5][c;$([c;H1]),$(c(c)(c)-[#6]),$(c-[#17,#35]),$(c-O-[#6]);!$(c-C=O);!$(c-C#N);!$(c-C(F)(F)F):6][c;$([c;H1]),$(c(c)(c)-[#6]),$(c-[#17,#35]),$(c-O-[#6]);!$(c-C=O);!$(c-C#N);!$(c-C(F)(F)F):7][c:2]2[c;!R2;$(c-[#6:102]),$([c;H1]);!$(c-C=*);!$(c-C#*):3][n;D2][c;D2][c;D2]1>>[c:1]1:[c:4]:[c:5]:[c:6]:[c:7]:[c:2]:1-[#6:3]=O",
1625
+ "rhs_classes": [
1626
+ "arylketones-aldehydes-2H-EDG"
1627
+ ],
1628
+ "syn_smarts": "O=[C;!R;$([C;H1:3]),$([C;H0](-c)-[#6:102]);!$(C-C=*);!$(C-C#*):3]-[c:2]1[c;H1:1][c;$([c;H1]),$(c(c)(c)-[#6]),$(c-[#17,#35]),$(c-O-[#6]);!$(c-C=O);!$(c-C#N);!$(c-C(F)(F)F):4][c;$([c;H1]),$(c(c)(c)-[#6]),$(c-[#17,#35]),$(c-O-[#6]);!$(c-C=O);!$(c-C#N);!$(c-C(F)(F)F):5][c;$([c;H1]),$(c(c)(c)-[#6]),$(c-[#17,#35]),$(c-O-[#6]);!$(c-C=O);!$(c-C#N);!$(c-C(F)(F)F):6][c;$([c;H1]),$(c(c)(c)-[#6]),$(c-[#17,#35]),$(c-O-[#6]);!$(c-C=O);!$(c-C#N);!$(c-C(F)(F)F):7]1>>[#6;H0:1]12-[#6]=[#6]-[#7]=[#6:3]-[#6:2]=1-[#6:7]=[#6:6]-[#6:5]=[#6:4]-2",
1629
+ "tags": [
1630
+ "Pomeranz-Fritsch",
1631
+ "heterocycle formation",
1632
+ "heterocycle",
1633
+ "isoquinoline",
1634
+ "transformation"
1635
+ ],
1636
+ "tier": 1
1637
+ },
1638
+ "pyrazole-1": {
1639
+ "allow_multiple_products": true,
1640
+ "description": "Pyrazole synthesis from 1,3-diketones and hydrazines.",
1641
+ "ld_data": {
1642
+ "display_smarts": "[#6:101]-C(=O)-C-C(=O)-[#6:102].[#7]-[#7]-[#6:103]>>[#6:101]-C=1-C=C(-[#6:102])-[#7](-[#6:103])-[#7]=1"
1643
+ },
1644
+ "long_name": "Pyrazole synthesis from 1,3-diketones and hydrazine",
1645
+ "retro_smarts": "[#6;!$([#6]=[#7,#8,#16]):4]-!@[#6;!R2:1]1:[#6:2]:[#6;!R2:3](-[#6;!$([#6]=[#7,#8,#16]):5]):[#7;$([#7;H1]),$([#7;H0]-[#6;!$([#6]=[#6,#7,#8,#16]):103]):7]:[#7:6]:1>>[#6:4]-[#6:1](=O)-[#6:2]-[#6:3](=O)(-[#6:5]).[#7:6]-[#7:7]",
1646
+ "rhs_classes": [
1647
+ "ketones-3keto",
1648
+ "hydrazines"
1649
+ ],
1650
+ "syn_smarts": "[#6;!$([#6]=[#7,#8,#16]):101]-[#6:1](=O)-[#6;H1,H2:2]-!@[#6:3](=O)-[#6;!$([#6]=[#7,#8,#16]):102].[#7;H2:6]-[#7;$([#7;H2]),$([#7;H1]-[#6;!$([#6]=[#6,#7,#8,#16]):103]):7]>>[#6:101]-[#6:1]1-[#6:2]=[#6:3](-[#6:102])-[#7:7]-[#7:6]=1",
1651
+ "tags": [
1652
+ "heterocycle formation",
1653
+ "heterocycle",
1654
+ "pyrazole"
1655
+ ],
1656
+ "tier": 1
1657
+ },
1658
+ "pyridine-1": {
1659
+ "description": "Hantzsch pyridine synthesis from two beta-ketoesters, an aldehyde, and ammonia (stepwise).",
1660
+ "ld_data": {
1661
+ "display_smarts": "[#6:101]-O-C(=O)-C-C(=O)-[#6:102].[#6:104]-O-C(=O)-C-C(=O)-[#6:105].O=C-[#6:103]>>[#6:101]-O-C(=O)-C=1-C(-[#6:102])=N-C(-[#6:105])=C(-C(=O)-O-[#6:104])-C(-[#6:103])=1"
1662
+ },
1663
+ "long_name": "Hantzsch pyridine synthesis from two beta-ketoesters, an aldehyde, and ammonia (stepwise).",
1664
+ "retro_smarts": "[C;!$([#6]=[#7,#8,#16]):101]-O-[#6:1](=[O:8])-!@[#6:2]1:[#6:3](-!@[#6;!$([#6]=[#7,#8,#16]):102]):[#7]:[#6:7](-!@[#6;!$([#6]=[#7,#8,#16]):105]):[#6:6](-!@[#6:5](=[O:9])-O-[#6;!$([#6]=[#7,#8,#16]):104]):[#6:4](-!@[#6;!$([#6]=[#7,#8,#16]):103]):1>>[C:101]-O-[#6:1](=[O:8])-[#6;H2:2]-[#6:3](=O)-[#6:102].[C:104]-O-[#6:5](=[O:9])-[#6;H2:6]-[#6:7](=O)-[#6:105].O=[#6;H1:4]-[#6:103]",
1665
+ "rhs_classes": [
1666
+ "esters-3keto",
1667
+ "esters-3keto",
1668
+ "aldehydes"
1669
+ ],
1670
+ "syn_smarts": "[C;!$([#6]=[#7,#8,#16]):101]-O-[#6:1](=O)-!@[#6;H2:2]-!@[#6:3](=O)-[#6;!$([#6]=[#7,#8,#16]):102].[C;!$([#6]=[#7,#8,#16]):104]-O-[#6:5](=O)-!@[#6;H2:6]-!@[#6:7](=O)-[#6;!$([#6]=[#7,#8,#16]):105].O=[#6;H1:4]-[#6;!$([#6]=[#7,#8,#16]):103]>>[#6:101]-O-[#6:1](=O)-[#6;H0:2]1-[#6:3](-[#6:102])=[#7]-[#6:7](-[#6:105])=[#6;H0:6](-[#6:5](=O)-O-[#6:104])-[#6;H0:4](-[#6:103])=1",
1671
+ "tags": [
1672
+ "Hantzsch",
1673
+ "heterocycle formation",
1674
+ "heterocycle",
1675
+ "pyridine"
1676
+ ],
1677
+ "tier": 1
1678
+ },
1679
+ "pyridine-2": {
1680
+ "description": "Krohnke pyridine synthesis from a 2-halo ketone and an alfa,beta-unsaturated ketone.",
1681
+ "ld_data": {
1682
+ "display_smarts": "[#6:101]-C(=O)-C-[#35].[#6:102]-C=C-C(=O)-[#6:103]>>[#6:101]-C=1-C=C(-[#6:102])-C=C(-[#6:103])-N=1"
1683
+ },
1684
+ "long_name": "Krohnke pyridine synthesis from 2-halo ketone and an alfa,beta-unsaturated ketone",
1685
+ "retro_smarts": "[#6;!$([#6]=[#6,#7,#8,#16]):101]-[c:1]1[c;H1:2][c;$([c;H0]-[#6]),$([c;H1]):3][c;$([c;H0]-[#6]),$([c;H1]):4][c:5](-!@[#6;$(c),$([C;!H0]),$(C(=O)-[O;H1]),$(C(=O)-OC):102])n1>>[#6:101]-[#6:1](=O)-[#6;H2:2]-[#17].[C:3]=[C:4]-[#6:5](=O)-[#6:102]",
1686
+ "rhs_classes": [
1687
+ "ketones-2halo",
1688
+ "ketones-unsaturated"
1689
+ ],
1690
+ "syn_smarts": "[#6;!$([#6]=[#6,#7,#8,#16]):101]-[#6:1](=O)-[#6;H2:2]-[#17,#35,#53].[C;$([C;H1]-[#6:103]),$([C;H2]):3]=!@[C;$([C;H1]),$([C;H0](=[C:3])(-[#6])-[#6:5]=O):4]-[#6:5](=O)-[#6;$(c),$([C;!H0]),$(C(=O)-[O;H1]),$(C(=O)-OC):102]>>[#6:101]-[#6:1]1=[#6;H1:2]-[#6:3]=[#6:4]-[#6:5](-[#6:102])=[#7]-1",
1691
+ "tags": [
1692
+ "Krohnke",
1693
+ "heterocycle formation",
1694
+ "heterocycle",
1695
+ "pyridine"
1696
+ ],
1697
+ "tier": 1
1698
+ },
1699
+ "pyridine-3": {
1700
+ "description": "Guareshi-Thorpe pyridine synthesis from a beta-ketoester, and a cyanoacetic ester.",
1701
+ "ld_data": {
1702
+ "display_smarts": "[#6]-O-C(=O)-C-C(=O)-[#6:101].N#C-[C:5]-[#6:6](=O)-O-[#6]>>O-C-1=C-C(-[#6:101])=C(-C#N)-C(-O)=N-1"
1703
+ },
1704
+ "long_name": "Guareshi-Thorpe pyridine synthesis",
1705
+ "retro_smarts": "[O;H1:8]-[c:1]1[c:2][c:3](-[#6:101])[c:6](-[C:5]#[N:4])[c:7](-[O;H1:9])[n;D2]1>>CO-[#6:1](=[O;H0:8])-[#6:2]-[#6:3](=O)-[#6:101].[N:4]#[C:5]-[C:6]-[#6:7](=[O;H0:9])-OC",
1706
+ "rhs_classes": [
1707
+ "esters-3keto",
1708
+ "esters-2cyano"
1709
+ ],
1710
+ "syn_smarts": "[C]-O-[#6:1](=O)-[C;$([C;H2]),$([C;H1](-C=O)(-C=O)-[C;!H0;!$(C=N)]):2]-[#6:3](=O)-[#6:101].[N:4]#[C:5]-[C;H2:6]-[#6:7](=O)-O-[C;!$([#6]=[#6,#7,#8,#16])]>>[O;H1]-[#6:1]1=[#6:2]-[#6:3](-[#6:101])=[#6;H0:6](-[C:5]#[N:4])-[#6:7](-O)=[#7]-1",
1711
+ "tags": [
1712
+ "Guareshi-Thorpe",
1713
+ "heterocycle formation",
1714
+ "heterocycle",
1715
+ "pyridine"
1716
+ ],
1717
+ "tier": 1
1718
+ },
1719
+ "pyridone-1": {
1720
+ "allow_multiple_products": true,
1721
+ "description": "Pyridone synthesis from cyanoacetamide and 1,3-diketones.",
1722
+ "ld_data": {
1723
+ "display_smarts": "[#7]-C(=O)-C-C#N.[#6:101]-C(=O)-C-C(=O)-[#6:102]>>N#C-C=1-C(=O)-N-C(-[#6:101])=C-C(-[#6:102])=1"
1724
+ },
1725
+ "long_name": "Pyridone synthesis from cyanoacetamide and 1,3-diketones",
1726
+ "retro_smarts": "[#6;!$([#6](-C=O)-C=O);!$(C=[C,N,O,S]):8]-[#6:5]1:[#6;!$([#6]-[#7,#8,#16]):6]:[#6:7](-[#6;!$([#6](-C=O)-C=O);!$(C=[C,N,O,S]):9]):[#6:2](-[#6:1]#N):[#6:3](=[O:10]):[#7;H1:4]:1>>[#7:4]-[#6:3](=[O:10])-[#6:2]-[#6:1]#N.[#6:9]-[#6:7](=O)-[#6:6]-[#6:5](-[#6:8])=O",
1727
+ "rhs_classes": [
1728
+ "cyanoacetamides",
1729
+ "ketones-3keto"
1730
+ ],
1731
+ "syn_smarts": "[#7;H2:4]-[#6:3](=O)-[#6;H2:2]-[#6:1]#N.[#6;!$([#6](-C=O)-C=O);!$(C=[C,N,O,S]):101]-[#6:5](=O)-[#6;H1,H2;!$([#6]-[#7,#8,#16]):6]-[#6;!R:7](=O)-[#6;!$([#6](-C=O)-C=O);!$(C=[C,N,O,S]):102]>>N#[#6:1]-[#6;H0:2]1-[#6:3](=O)-[#7;H1:4]-[#6:5](-[#6:101])=[#6:6]-[#6:7](-[#6:102])=1",
1732
+ "tags": [
1733
+ "heterocycle formation",
1734
+ "heterocycle",
1735
+ "pyridone"
1736
+ ],
1737
+ "tier": 1
1738
+ },
1739
+ "pyrimidine-1": {
1740
+ "description": "Pinner pyrimidine synthesis.",
1741
+ "ld_data": {
1742
+ "display_smarts": "[#6:101]-C(=O)-C-C(=O)-[#6:102].[#6:103]-C(=[#7])-[#7]>>[#6:101]-C=1-N=C(-[#6:103])-N=C(-[#6:102])-C=1"
1743
+ },
1744
+ "long_name": "Pinner pyrimidine synthesis from a 1,3-diketones and an amidine",
1745
+ "retro_smarts": "[#6:5]-[c:4]1[c;$(c-[#6;$(c),$([C;!H0])]),$([c;H1]):3][c:2](-[#6:1])[n:8][c:7](-!@[#6;!$(C=[C,N,S,O]):6])[n:9]1>>[#6:1]-[#6:2](=O)-[#6:3]-[#6:4](=O)-[#6:5].[#6:6]-[#6:7](=[#7:8])-[#7:9]",
1746
+ "rhs_classes": [
1747
+ "ketones-3keto",
1748
+ "amidines"
1749
+ ],
1750
+ "syn_smarts": "[#6:101]-!@[#6:2](=O)-!@[#6;$([C;H2]),$([C;H1]-[#6;$(c),$([C;!H0])]):3]-!@[#6:4](=O)-!@[#6:102].[#6;!$(C=[C,N,S,O]):103]-[#6:6](=[#7;H1:7])-[#7;H2:8]>>[#6:101]-[#6:2]1=[#7;H0:7]-[#6:6](-[#6:103])=[#7;H0:8]-[#6:4](-[#6:102])=[#6:3]-1",
1751
+ "tags": [
1752
+ "heterocycle formation",
1753
+ "heterocycle",
1754
+ "pyrimidine"
1755
+ ],
1756
+ "tier": 1
1757
+ },
1758
+ "pyrimidinedione-1": {
1759
+ "description": "Pyrimidinedione synthesis from amino-acrylates and isocyanates.",
1760
+ "ld_data": {
1761
+ "display_smarts": "[#7]-C=C-C(=O)-O-C.[#6:101]-N=C=O>>N-1-C=C-C(=O)-N(-[#6:101])-C(=O)-1"
1762
+ },
1763
+ "long_name": "Pyrimidinedione synthesis from amino-acrylates and isocyanates",
1764
+ "retro_smarts": "[#7;$([#7;H1]),$([#7;H0][#6;!$(C=[O,N,S])]):1]1:[#6;!$(c(:a)(:a):a):6]:[#6;!$(c(:a)(:a):a):7]:[#6:2](=[O:8]):[#7:4](-!@[#6:3]):[#6:5]:1(=[O:9])>>[#7:1]-[#6:6]=[#6:7]-[#6:2](=[O:8])-O-C.[#6:3]-[#7:4]=[#6:5]=[O:9]",
1765
+ "rhs_classes": [
1766
+ "acrylates-amino",
1767
+ "isocyanates"
1768
+ ],
1769
+ "syn_smarts": "[#7;$([#7;H1](-[#6;!$(C=[C,O,N,S]);!$([c;R2])])-[#6;$([#6]=[#6]);!$(C=[O,N,S]):6]),$([#7;H2]):1]-[#6:6]=[#6:7]-[#6:2](=O)-O-[C;!$(C=[O,N,S])].[#6:101]-[#7:4]=[#6:5]=O>>[#7:1]1-[#6:6]=[#6:7]-[#6:2](=O)-[#7:4](-[#6:101])-[#6:5](=O)-1",
1770
+ "tags": [
1771
+ "heterocycle formation",
1772
+ "heterocycle",
1773
+ "pyrimidinedione"
1774
+ ],
1775
+ "tier": 1
1776
+ },
1777
+ "pyrimidinedione-2": {
1778
+ "description": "Bicyclic pyrimidinedione synthesis from 2-aminobenzoates and isocyanates.",
1779
+ "ld_data": {
1780
+ "display_smarts": "[#7]-C=1-C=C-C=C-C=1-C(=O)-O-[#6].[#6:101]-N=C=O>>N-1-C=2-C=C-C=C-C=2-C(=O)-N(-[#6:101])-C(=O)-1"
1781
+ },
1782
+ "long_name": "Bicyclic pyrimidinedione synthesis from 2-aminobenzoates and isocyanates",
1783
+ "retro_smarts": "[#7;$([#7;H1]),$([#7;H0]-[#6;!$(C=[O,N,S])]):1]1:[c;R2,R3:6]:[c;R2:7]:[#6:2](=[O:8]):[#7:4](-!@[#6:3]):[#6:5]:1(=[O:9])>>[#7:1]-[c:6][c:7]-[#6:2](=[O:8])-O-C.[#6:3]-[#7:4]=[#6:5]=[O:9]",
1784
+ "rhs_classes": [
1785
+ "benzoates-2amino",
1786
+ "isocyanates"
1787
+ ],
1788
+ "syn_smarts": "[#7;$([#7;H1](-[#6;!$(C=[O,N,S])])-[c:6]),$([#7;H2]):1]-[c:6][c:7]-[#6:2](=O)-O-[C;!$(C=[O,N,S])].[#6:101]-[#7:4]=[#6:5]=O>>[#7:1]1-[c:6][c:7]-[#6:2](=O)-[#7:4](-[#6:101])-[#6:5](=O)-1",
1789
+ "tags": [
1790
+ "heterocycle formation",
1791
+ "heterocycle",
1792
+ "pyrimidinedione"
1793
+ ],
1794
+ "tier": 1
1795
+ },
1796
+ "pyrimidone-1": {
1797
+ "description": "Biginelli 2-pyrimidone synthesis.",
1798
+ "ld_data": {
1799
+ "display_smarts": "[#6:101]-C(=O)-C-C(=O)-O-[#6].[#6:102]-C(=O)>>[#6:101]-C=1-N-C(=O)-N-C(-[#6:102])-C(-C(=O)-O-[#6])=1"
1800
+ },
1801
+ "long_name": "Biginelli synthesis of 2-pyrimidones from a beta-ketoester, an aldehyde and urea",
1802
+ "retro_smarts": "[#6:101]-[#6:2]1-N-C(=O)-N-[#6:5](-!@[#6:102])-[#6:3](-[#6;!R:4](=[O:7])-[O:8]-[#6:6])=1>>[#6:101]-[#6:2](=O)-[#6:3]-[#6:4](=[O:7])-[O:8]-[#6:6].[#6:102]-[#6;H1:5](=O)",
1803
+ "rhs_classes": [
1804
+ "esters-3keto",
1805
+ "aldehydes"
1806
+ ],
1807
+ "syn_smarts": "[#6:101]-[#6:2](=O)-[#6;H2:3]-[#6;!R:4](=O)-O-[#6:6].[#6:102]-[C;H1:5]=O>>[#6:101]-[#6:2]1-N-C(=O)-N-[#6:5](-[#6:102])-[#6;H0:3](-[#6:4](=O)-O-[#6:6])=1",
1808
+ "tags": [
1809
+ "Biginelli",
1810
+ "heterocycle formation",
1811
+ "heterocycle",
1812
+ "pyrimidone"
1813
+ ],
1814
+ "tier": 1
1815
+ },
1816
+ "pyrimidone-2": {
1817
+ "description": "Biginelli 2-mercaptopyrimidine synthesis.",
1818
+ "ld_data": {
1819
+ "display_smarts": "[#6:101]-C(=O)-C-C(=O)-O-[#6].[#6:102]-C=O>>[#6:101]-C=1-N-C(=S)-N-C(-[#6:102])-C(-C(=O)-O-[#6])=1"
1820
+ },
1821
+ "long_name": "Biginelli synthesis of 2-mercaptopyrimidines from a beta-ketoester, an aldehyde and thiourea",
1822
+ "retro_smarts": "[#6:101]-[#6:2]1-[#7;D2;H1]-[#6](=[S;X1])-[#7;D2;H1]-[#6:5](-!@[#6:102])-[#6:3](-[#6;!R:4](=[O:7])-[O:8]-[#6:6])=1>>[#6:101]-[#6:2](=O)-[#6:3]-[#6:4](=[O:7])-[O:8]-[#6:6].[#6:102]-[#6;H1:5](=O)",
1823
+ "rhs_classes": [
1824
+ "esters-3keto",
1825
+ "aldehydes"
1826
+ ],
1827
+ "syn_smarts": "[#6:101]-[#6:2](=O)-[#6;H2:3]-[#6;!R:4](=O)-O-[#6:6].[#6:102]-[C;H1:5]=O>>[#6:101]-[#6:2]1-N-C(=S)-N-[#6:5](-[#6:102])-[#6;H0:3](-[#6:4](=O)-O-[#6:6])=1",
1828
+ "tags": [
1829
+ "Biginelli",
1830
+ "heterocycle formation",
1831
+ "heterocycle",
1832
+ "pyrimidone"
1833
+ ],
1834
+ "tier": 1
1835
+ },
1836
+ "pyrrole-1": {
1837
+ "description": "Knorr pyrrole synthesis.",
1838
+ "ld_data": {
1839
+ "display_smarts": "[#6:101]-[#6](=O)-[#6]-[#6](=O)-O-[#6].[#6:102]-[#6](=O)-[#6]-[#6](=O)-O-[#6]>>[#6:101]-[#6]=1-[#6](-C(=O)-O-[#6])=[#6](-[#6:102])-N-[#6](-C(=O)-O-[#6])=1"
1840
+ },
1841
+ "long_name": "Knorr pyrrole synthesis from two beta-ketoesters",
1842
+ "retro_smarts": "[#6:101]-[c:2]1[c:7](-[#6:8](=[O:12])-[#8:13]-[#6:9])[c:6](-[#6:102])[n;D2][c:3](-[#6:4](=[O:10])-[#8:11]-[#6:5])1>>[#6:101]-[C:2](=O)-[C:3]-[C:4](=[O:10])-[O:11]-[C:5].[#6:102]-[C:6](=O)-[C:7]-[C:8](=[O:12])-[O:13]-[C:9]",
1843
+ "rhs_classes": [
1844
+ "esters-3keto",
1845
+ "esters-3keto"
1846
+ ],
1847
+ "syn_smarts": "[#6:101]-[C:2](=O)-[C;H2:3]-[C:4](=O)-O-[C:5].[#6:102]-[C:6](=O)-[C;H2:7]-[C:8](=O)-O-[C:9]>>[#6:101]-[#6:2]1-[#6;H0:7](-[#6:8](=O)-O-[C:9])=[#6:6](-[#6:102])-[N;H1]-[#6;H0:3](-[#6:4](=O)-O-[#6:5])=1",
1848
+ "tags": [
1849
+ "Knorr",
1850
+ "heterocycle formation",
1851
+ "heterocycle",
1852
+ "pyrrole"
1853
+ ],
1854
+ "tier": 1
1855
+ },
1856
+ "pyrrole-2": {
1857
+ "description": "Paal-Knorr pyrrole synthesis.",
1858
+ "ld_data": {
1859
+ "display_smarts": "[#6:101]-C(=O)-C-C-C(=O)-[#6:102].[#6:103]-[#7]>>[#6:101]-C-1=C-C=C(-[#6:102])-N(-[#6:103])-1"
1860
+ },
1861
+ "long_name": "Paal-Knorr pyrrole synthesis",
1862
+ "retro_smarts": "[#6:101]-[#6:2]1:[#6:3]:[#6:4]:[#6:5](-!@[#6:102]):[#7:6](-!@[#6:103]):1>>[#6:101]-[C:2](=O)-[C:3]-[C:4]-[C:5](=O)-[#6:102].[#6:103]-[N:6]",
1863
+ "rhs_classes": [
1864
+ "ketones-4keto",
1865
+ "amines-prim"
1866
+ ],
1867
+ "syn_smarts": "[#6:101]-[C;!R:2](=O)-[C;!R;H1,H2:3]-[C;H1,H2:4]-[C:5](=O)-[#6:102].[#6;!$([#6]=[#6,#7,#8,#16]):103]-[N;H2:6]>>[#6:101]-[#6:2]1=[#6:3]-[#6:4]=[#6:5](-[#6:102])-[#7;H0:6](-[#6:103])-1",
1868
+ "tags": [
1869
+ "Paal-Knorr",
1870
+ "heterocycle formation",
1871
+ "heterocycle",
1872
+ "pyrrole"
1873
+ ],
1874
+ "tier": 1
1875
+ },
1876
+ "quinazoline-1": {
1877
+ "description": "Quinazoline synthesis from a quinazolinone and a primary or secondary amine.",
1878
+ "ld_data": {
1879
+ "display_smarts": "O=C-1-N-C=N-C-2=C-1-C=C-C=C-2.[#6:101]-[#7]>>[#6:101]-N-C-1=N-C=N-C-2=C-1-C=C-C=C-2"
1880
+ },
1881
+ "long_name": "Quinazoline synthesis from a quinazolinone and a primary or secondary amine",
1882
+ "retro_smarts": "[#7;$([#7;H2]),$([#7;H1](-c)-[#6;!$(C=[C,N,O,S]):12]),$([#7;H0](-c)(-[#6;!$(C=[C,N,O,S]):12])-[#6;!$(C=[C,N,O,S])]):11]-!@[c:10]1[n:9][c:8][n:7][c:6]2[a:5][a:4][a:3][a:2][c:1]12>>O=[c:10]1[n;H1:9][c:8][n:7][c:6]2[a:5][a:4][a:3][a:2][c:1]12.[#7:11]",
1883
+ "rhs_classes": [
1884
+ "quinazolinones",
1885
+ "amines-primsec"
1886
+ ],
1887
+ "syn_smarts": "O=[c:1]1[n:2][c;!$(c=[C,N,O,S]):3][n:4][c:5]2[c:6]1[a:7][a:8][a:9][a:10]2.[#7;$([#7;H3]),$([#7;H2]-[#6;!$(C=[C,N,O,S]):101]),$([#7;H1](-[#6;!$(C=[C,N,O,S])])-[#6;!$(C=[C,N,O,S]):101]):13]>>[#7:13]-[c:1]1[n;H0:2][c:3][n:4][c:5]2[c:6]1[a:7][a:8][a:9][a:10]2",
1888
+ "tags": [
1889
+ "heterocycle formation",
1890
+ "heterocycle",
1891
+ "quinazoline"
1892
+ ],
1893
+ "tier": 1
1894
+ },
1895
+ "quinazolinone-1": {
1896
+ "description": "Quinazolinone synthesis from a 2-carboxy aniline, a primary amine, and an aldehyde.",
1897
+ "ld_data": {
1898
+ "display_smarts": "[#7]-C=1-C=C-C=C-C=1-C(-[#8])=O.[#6:101]-[#7].C(=O)-[#6:102]>>[#6:101]-N-1-C(-[#6:102])=N-C=2-C=C-C=C-C=2-C-1=O"
1899
+ },
1900
+ "long_name": "Quinazolinone Synthesis from a 2-carboxy aniline, a primary amine, and an aldehyde",
1901
+ "retro_smarts": "[#8:9]=[#6:7]1:[#7;$([#7;H1]),$([#7;H0]-!@[#6;!$(C=[C,N,O,S]):101]):11]:[#6;$([#6;H1]),$([#6;H0]-!@[#6;!$(C=[C,N,O,S]):102]):12]:[#7:8]:[#6:2]:2:[a:3]:[a:4]:[a:5]:[a:6]:[#6:1]:1:2>>[#7:8]-[#6:2]1:[a:3]:[a:4]:[a:5]:[a:6]:[#6:1]:1-[#6:7](-[#8])=[#8:9].[#7:11].[#6:12]=O",
1902
+ "rhs_classes": [
1903
+ "anilines-2COOH",
1904
+ "amines-primsec",
1905
+ "aldehydes"
1906
+ ],
1907
+ "syn_smarts": "[#7;H2:7]-[c:5]1[a:4][a:3][a:2][a:1][c:6]1-[#6:10](-[#8;H1])=[O:11].[#7;$([#7;H3]),$([#7;H2]-[#6;!$(C=[C,N,O,S]):101]):9].[#6;$([#6;H2]),$([#6;H1]-[#6;!$(C=[C,N,O,S]):102]):8]=O>>[#7:9]1-[#6:8]=[#7;H0:7]-[#6:5]2:[a:4]:[a:3]:[a:2]:[a:1]:[#6:6]:2-[#6:10](=[#8:11])-1",
1908
+ "tags": [
1909
+ "heterocycle formation",
1910
+ "heterocycle",
1911
+ "quinazolinone"
1912
+ ],
1913
+ "tier": 1
1914
+ },
1915
+ "quinazolinone-2": {
1916
+ "description": "Niementowski quinazolinone synthesis from a 2-carboxy aniline, and a primary amide.",
1917
+ "ld_data": {
1918
+ "display_smarts": "[#7]-C=1-C=C-C=C-C(-C(=O)-O)=1.[#7]-C(=O)-[#6:101]>>C=1-2-C(=O)-N-C(-[#6:101])=N-C=1-C=C-C=C-2"
1919
+ },
1920
+ "long_name": "Niementowski quinazolinone synthesis",
1921
+ "retro_smarts": "[#8:9]=[#6:7]1:[#7;$([#7;H1]):11]:[#6;$([#6;H1]),$([#6;H0]-!@[#6;!$(C=[C,N,O,S]):101]):12]:[#7:8]:[#6:2]:2:[a:3]:[a:4]:[a:5]:[a:6]:[#6:1]:1:2>>[#7:8]-[#6:2]1:[a:3]:[a:4]:[a:5]:[a:6]:[#6:1]:1-[#6:7](-[#8])=[#8:9].[#7:11]-[#6:12]=O",
1922
+ "rhs_classes": [
1923
+ "anilines-2COOH",
1924
+ "amides-prim"
1925
+ ],
1926
+ "syn_smarts": "[#7;H2:7]-[c:5]2[a:4][a:3][a:2][a:1][c:6]2-[#6:8](-[#8;H1])=O.[C;$([C;H1]),$([C;H0]-[#6;!$(C=[C,N,O,S]):102]):10](=O)-[#7;H2:9]>>[#7;H1:9]1-[#6:10]=[#7;H0:7]-[c:5]2[a:4][a:3][a:2][a:1][c:6]2-[#6:8](=O)-1",
1927
+ "tags": [
1928
+ "Niementowski",
1929
+ "heterocycle formation",
1930
+ "heterocycle",
1931
+ "quinazolinone"
1932
+ ],
1933
+ "tier": 1
1934
+ },
1935
+ "quinoline-1": {
1936
+ "description": "Quinoline synthesis from a 2-amino benzaldehyde and a ketone.",
1937
+ "ld_data": {
1938
+ "display_smarts": "[#7]-C-1=C-C=C-C=C-1-C=O.[#6:101]-C-C(=O)-[#6:102]>>N-1=C(-[#6:102])-C(-[#6:101])=C-C=2-C=C-C=C-C=2-1"
1939
+ },
1940
+ "long_name": "Quinoline synthesis",
1941
+ "retro_smarts": "[c;$([c;H1]),$([c;H0]-[#6;!$(C=[C,N,O,S]):8]):3]1[c;H1:4][c;!$(c-[C,N]);R2:5][c;!$(c-[C,N]);R2:6][n:1][c:2]1-[#6:7]>>[#7:1]-[c:6][c:5]-[#6:4]=O.[#6:3]-[#6:2](=O)-[#6:7]",
1942
+ "rhs_classes": [
1943
+ "anilines-2formyl",
1944
+ "ketones-2unsub"
1945
+ ],
1946
+ "syn_smarts": "[#7;H2:1]-[c:2][c:7]-[#6;H1:8]=O.[#6;$([#6;H3]),$([#6;H2]-[#6;!$(C=[C,N,O,S]):101]):10]-[#6:11](=O)-[#6:102]>>[#7;H0:1]1=[#6:11](-[#6:102])-[#6:10]=[#6:8]-[c:7][c:2]-1",
1947
+ "tags": [
1948
+ "heterocycle formation",
1949
+ "heterocycle",
1950
+ "Friedlander",
1951
+ "quinoline"
1952
+ ],
1953
+ "tier": 1
1954
+ },
1955
+ "quinoline-2": {
1956
+ "description": "Niementowski quinoline synthesis from a 2-carboxy aniline and a ketone.",
1957
+ "ld_data": {
1958
+ "display_smarts": "[#7]-C-1=C-C=C-C=C-1-C(=O)-[#8].[#6:101]-C-C(=O)-[#6:102]>>N-1=C(-[#6:102])-C(-[#6:101])=C(-[#8])-C=2-C=C-C=C-C=2-1"
1959
+ },
1960
+ "long_name": "Niementowski quinoline synthesis",
1961
+ "retro_smarts": "[c;$([c;H1]),$([c;H0]-[#6;!$(C=[C,N,O,S]):8]):3]1[c:4](-[#8;H1:8])[c;!$(c-[C,N]);R2:5][c;!$(c-[C,N]);R2:6][n:1][c:2]1-[#6;!$(C=[C,N,O,S]):7]>>[#7:1]-[c:6][c:5]-[#6:4](=O)-[#8;H1:8].[#6:3]-[#6:2](=O)-[#6:7]",
1962
+ "rhs_classes": [
1963
+ "anilines-2COOH",
1964
+ "ketones-2unsub"
1965
+ ],
1966
+ "syn_smarts": "[#7;H2:1]-[c:2][c:7]-[#6:8](=[#8:9])-[O;H1].[#6;$([#6;H3]),$([#6;H2]-[#6;!$(C=[C,N,O,S]):101]):10]-[#6:11](=O)-[#6;!$(C=[C,N,O,S]):102]>>[#7;H0:1]1=[#6:11](-[#6:102])-[#6:10]=[#6:8](-[#8;H1:9])-[c:7][c:2]-1",
1967
+ "tags": [
1968
+ "Niementowski",
1969
+ "heterocycle formation",
1970
+ "heterocycle",
1971
+ "quinoline"
1972
+ ],
1973
+ "tier": 1
1974
+ },
1975
+ "rubottom": {
1976
+ "description": "Rubottom oxidation: alfa hydroxylation of an enolizable ketone via the corresponding silyl enol ether.",
1977
+ "ld_data": {
1978
+ "display_smarts": "[#6:102]-C-C(=O)-[#6:101]>>[#6:102]-C(-[#8])-C(=O)-[#6:101]"
1979
+ },
1980
+ "long_name": "Rubottom oxidation",
1981
+ "retro_smarts": "[C;$([C;H1]),$([C;H0]-[#6;$(c),$([C;!H0]):101]):2](=[O:1])-[C;$([C;H2]),$([C;H1]-[#6;$(c),$([C;!H0]):102]):3]-[O;H1]>>[C:2](=[O:1])-[C:3]",
1982
+ "rhs_classes": [
1983
+ "ketones-enolizable"
1984
+ ],
1985
+ "syn_smarts": "[C;$([C;H1]),$([C;H0]-[#6;$(c),$([C;!H0]):101]):2](=O)-[C;$([C;H3]),$([C;H2]-[#6;$(c),$([C;!H0]):102]):3]>>[C:2](=O)-[C:3]-[O;H1]",
1986
+ "tags": [
1987
+ "Rubottom",
1988
+ "oxidation",
1989
+ "transformation"
1990
+ ],
1991
+ "tier": 1
1992
+ },
1993
+ "sonogashira": {
1994
+ "description": "Sonogashira Coupling: Arylation of an alkyne with an aryl/vinyl halide.",
1995
+ "ld_data": {
1996
+ "display_smarts": "Br-[#6:201].[#6:101]-C#C>>[#6:101]-C#C-[#6:201] |$;Aryl_p;;;;;;;Aryl_p$|"
1997
+ },
1998
+ "long_name": "Sonogashira coupling",
1999
+ "retro_smarts": "[#6;$(c),$(C=C):101]-!@[#6:2]#[#6:3]-[#6;!$([#6]=[#6,#7,#8,#16]):102]>>[#6:101]-Br.[#6;H1:2]#[#6:3]-[#6:102]",
2000
+ "rhs_classes": [
2001
+ "halides-aryl-vinyl",
2002
+ "alkynes-monosub"
2003
+ ],
2004
+ "syn_smarts": "[#6;$(c),$(C=C):101]-[Cl,Br,I].[#6;H1:2]#[#6:3]-[#6;!$([#6]=[#6,#7,#8,#16]):102]>>[#6:101]-[#6;H0:2]#[#6:3]-[#6:102]",
2005
+ "tags": [
2006
+ "Sonagashira",
2007
+ "C-C bond formation",
2008
+ "C-C"
2009
+ ],
2010
+ "tier": 1
2011
+ },
2012
+ "spiro-chromanone": {
2013
+ "description": "Spiro-chromanone synthesis from an o-hydroxyacetophenone and a cyclohexanone.",
2014
+ "ld_data": {
2015
+ "display_smarts": "[#8]-C=1-C=C-C=C-C=1-C(=O)-[#6].C-1(=O)-C-C-C-C-C-1>>O=C-1-C-C-2(-C-C-C-C-C-2)-O-C=2-C=C-C=C-C-1=2"
2016
+ },
2017
+ "long_name": "Spiro-chromanone Synthesis",
2018
+ "retro_smarts": "[O:16]=[#6:8]-1-[#6;H2:9]-[#6:10]-2(-[C;H1,H2:11][C;!$(C=[#6,#7,#8,#16]):12][C,N,O:13][C;!$(C=[#6,#7,#8,#16]):14][C;H1,H2:15]-2)-[#8:1]-[c:2]2[a:3][a:4][a:5][a:6][c:7]-12>>[O:1]-[c:2]1[a:3][a:4][a:5][a:6][c:7]1(-[C:8](=[O:16])-[C:9]).[C:10]1(=O)[C:11][C:12][*:13][C:14][C:15]1",
2019
+ "rhs_classes": [
2020
+ "acetophenones-2OH",
2021
+ "cyclohexanones"
2022
+ ],
2023
+ "syn_smarts": "[O;H1:1]-[c:2]1[a:3][a:4][a:5][a:6][c:7]1(-[C:8](=O)-[C;H3:9]).[C:10]1(=O)[C;H1,H2:11][C;!$(C=[#6,#7,#8,#16]):12][C,N,O:13][C;!$(C=[#6,#7,#8,#16]):14][C;H1,H2:15]1>>O=[#6:8]-1-[#6;H2:9]-[#6:10]-2(-[#6:11]-[#6:12]-[*:13]-[#6:14]-[#6:15]-2)-[#8;H0:1]-[c:2]2[a:3][a:4][a:5][a:6][c:7]-12",
2024
+ "tags": [
2025
+ "heterocycle formation",
2026
+ "heterocycle",
2027
+ "spiro-chromanone",
2028
+ "chromanone"
2029
+ ],
2030
+ "tier": 1
2031
+ },
2032
+ "stille": {
2033
+ "description": "Stille Coupling: aryl C-C coupling from an aryl or vinyl halide and an organostannane.",
2034
+ "ld_data": {
2035
+ "display_smarts": "Br-[#6:201].[#6]-C-C-C-[Sn](-[#6:202])(-C-C-C-[#6])-C-C-C-[#6]>>[#6:202]-[#6:201] |$;Aryl_p;;;;;;Aryl_p;;;;;;;;;Aryl_p;Aryl_p$|"
2036
+ },
2037
+ "long_name": "Stille coupling",
2038
+ "retro_smarts": "[#6;$(c),$(C=C):1]-!@[#6;$(C=C),$(c):2]>>[#6:1]-Br.[#6:2]-[#50](-CCCC)(-CCCC)-CCCC",
2039
+ "rhs_classes": [
2040
+ "halides-aryl-vinyl",
2041
+ "organostannanes"
2042
+ ],
2043
+ "syn_smarts": "[#6;$(c),$(C=C):101]-[Cl,Br,I].[#6;$([#6]=[#6]),$(c):102]-[#50](-CCCC)(-CCCC)-CCCC>>[#6:101]-[#6:102]",
2044
+ "tags": [
2045
+ "Stille",
2046
+ "organostannane",
2047
+ "C-C bond formation",
2048
+ "C-C"
2049
+ ],
2050
+ "tier": 2
2051
+ },
2052
+ "stille-2": {
2053
+ "description": "Stille Carbonylative Coupling: aryl C-C coupling with CO insertion from an aryl or vinyl halide and an organostannane.",
2054
+ "ld_data": {
2055
+ "display_smarts": "Br-[#6:201].[#6]-C-C-C-[Sn](-[#6:202])(-C-C-C-[#6])-C-C-C-[#6]>>[#6:202]-C(=O)-[#6:201] |$;Aryl_p;;;;;;Aryl_p;;;;;;;;;Aryl_p;;;Aryl_p$|"
2056
+ },
2057
+ "long_name": "Stille carbonylative coupling",
2058
+ "retro_smarts": "[#6;$(c),$(C=C):1]-!@C(=O)-[#6;$(C=C),$(c):2]>>[#6:1]-Br.[#6:2]-[#50](-CCCC)(-CCCC)-CCCC",
2059
+ "rhs_classes": [
2060
+ "halides-aryl-vinyl",
2061
+ "organostannanes"
2062
+ ],
2063
+ "syn_smarts": "[#6;$(c),$(C=C):101]-[Cl,Br,I].[#6;$(C=C),$(c):102]-[#50](-CCCC)(-CCCC)-CCCC>>[#6:101]-C(=O)-[#6:102]",
2064
+ "tags": [
2065
+ "Stille",
2066
+ "organostannane",
2067
+ "C-C bond formation",
2068
+ "C-C",
2069
+ "CO insertion"
2070
+ ],
2071
+ "tier": 2
2072
+ },
2073
+ "sulfonamide-1": {
2074
+ "description": "Sulfonamide synthesis from a sulfonyl chloride and a primary or secondary amine.",
2075
+ "ld_data": {
2076
+ "display_smarts": "[#6:101]-[S](=O)(=O)-[Cl].[#7]-[#6:102]>>[#6:102]-N-S(=O)(=O)-[#6:101]"
2077
+ },
2078
+ "long_name": "Sulfonamide coupling",
2079
+ "retro_smarts": "[#6:3]-[S:1](=[O:4])(=[O:5])-!@[N;$([N;H2]),$([N;H0](-[#6;!$(C=[C,N,O,S]):103])-[#6;!$(C=[C,N,O,S]):102]),$([N;H1]-[#6;!$(C=[C,N,O,S]):102]):2]>>[#6:3]-[S:1](=[O:4])(=[O:5])-Cl.[N:2]",
2080
+ "rhs_classes": [
2081
+ "sulfonyl_chlorides",
2082
+ "amines-primsec"
2083
+ ],
2084
+ "syn_smarts": "[#6:101]-[S:1](=O)(=O)-[Cl].[N;$([N;H3]),$([N;H1](-[#6;!$(C=[C,N,O,S]):103])-[#6;!$(C=[C,N,O,S]):102]),$([N;H2]-[#6;!$(C=[C,N,O,S]):102]):2]>>[#6:101]-[S:1](=O)(=O)-[N:2]",
2085
+ "tags": [
2086
+ "sulfonamide"
2087
+ ],
2088
+ "tier": 1
2089
+ },
2090
+ "sulfone-1": {
2091
+ "description": "Oxidation of a thioether to a sulfone.",
2092
+ "ld_data": {
2093
+ "display_smarts": "[#6:101]-[S]-[#6:102]>>[#6:102]-[S](=O)(=O)-[#6:101]"
2094
+ },
2095
+ "long_name": "Oxidation of a thioether to a sulfone",
2096
+ "retro_smarts": "[#6:101][#16;X4:2](=O)(=O)[#6:102]>>[#6:101][#16;X2:2][#6:102]",
2097
+ "syn_smarts": "[#6:101][#16;X2:2][#6:102]>>[#6:101][#16;X4:2](=O)(=O)[#6:102]",
2098
+ "tags": [
2099
+ "sulfone",
2100
+ "oxidation",
2101
+ "transformation"
2102
+ ],
2103
+ "tier": 1
2104
+ },
2105
+ "sulfone-2": {
2106
+ "description": "Oxidation of a sulfoxide to a sulfone.",
2107
+ "ld_data": {
2108
+ "display_smarts": "[#6:102]-[S](=O)-[#6:101]>>[#6:101]-[S](=O)(=O)-[#6:102]"
2109
+ },
2110
+ "long_name": "Oxidation of a sulfoxide to a sulfone",
2111
+ "retro_smarts": "[#6:101][#16;X4:2](=[O:3])(=O)[#6:102]>>[#6:101][#16;X3:2](=[O:3])[#6:102]",
2112
+ "syn_smarts": "[#6:101][#16;X3:2](=O)[#6:102]>>[#6:101][#16;X4:2](=O)(=O)[#6:102]",
2113
+ "tags": [
2114
+ "sulfone",
2115
+ "oxidation",
2116
+ "transformation"
2117
+ ],
2118
+ "tier": 1
2119
+ },
2120
+ "sulfoxide": {
2121
+ "description": "Oxidation of a thioether to a sulfoxide.",
2122
+ "ld_data": {
2123
+ "display_smarts": "[#6:101]-[S]-[#6:102]>>[#6:102]-[S](=O)-[#6:101]"
2124
+ },
2125
+ "long_name": "Oxidation of a thioether to a sulfoxide",
2126
+ "retro_smarts": "[#6:101][#16;X3:2](=O)[#6:102]>>[#6:101][#16;X2:2][#6:102]",
2127
+ "syn_smarts": "[#6:101][#16;X2:2][#6:102]>>[#6:101][#16;X3:2](=O)[#6:102]",
2128
+ "tags": [
2129
+ "sulfoxide",
2130
+ "oxidation",
2131
+ "transformation"
2132
+ ],
2133
+ "tier": 1
2134
+ },
2135
+ "suzuki": {
2136
+ "description": "Suzuki coupling: aryl C-C coupling from an aryl halide and an aryl/vinyl boronate.",
2137
+ "ld_data": {
2138
+ "display_smarts": "Br-[#6:201].[#8]-[#5](-[#8])-[#6:202]>>[#6:202]-[#6:201] |$;Aryl_p;;;;Aryl_p;Aryl_p;Aryl_p$|"
2139
+ },
2140
+ "long_name": "Suzuki coupling of aryl/vinyl boronates with aryl/vinyl halides",
2141
+ "retro_smarts": "[#6;$(c),$(C=C);!$(C=C-[#6]=[#6,#7,#8,#16]):1]-!@[#6;$(c),$(C=C):2]>>[#6:1]-Br.[#6:2]-B(-O)-O",
2142
+ "rhs_classes": [
2143
+ "halides-aryl-vinyl",
2144
+ "boronates-aryl-vinyl"
2145
+ ],
2146
+ "syn_smarts": "[#6;$(c),$(C=C);!$(C=C-[#6]=[#6,#7,#8,#16]):101]-[Cl,Br,I].[#6;$(c),$(C=C):102]-B(-O)O>>[#6:101]-[#6:102]",
2147
+ "tags": [
2148
+ "Suzuki",
2149
+ "C-C bond formation",
2150
+ "C-C",
2151
+ "boronic acid",
2152
+ "boronic ester",
2153
+ "boronate"
2154
+ ],
2155
+ "tier": 1
2156
+ },
2157
+ "suzuki-2": {
2158
+ "description": "Suzuki coupling: C-C coupling of an aryl halide and a trifluoroborate.",
2159
+ "ld_data": {
2160
+ "display_smarts": "Br-[#6:201].[#9]-[#5-](-[#9])(-[#9])-[#6:101]>>[#6:201]-[#6:101] |$;Aryl_p;;;;;;Aryl_p;$|"
2161
+ },
2162
+ "long_name": "Suzuki coupling of trifluoroborates and with aryl/vinyl halides",
2163
+ "retro_smarts": "[#6;$(c),$(C=C);!$(C=C-[#6]=[#6,#7,#8,#16]):1]-!@[#6;$(c),$(C=C),$(C#C),$(C(=O)(-[#6;$(c),$(C=C):1])-[#6]),$(C(F)(F)F),$(C);!$(C(=O)-[#7,#8,#16]);!$(C(-[#6;$(c),$(C=C):1])-[#6]=[#6,#7,#8,#16]):2]>>[#6:1]-Br.[#6:2]-[#5;-](F)(F)F",
2164
+ "rhs_classes": [
2165
+ "halides-aryl-vinyl",
2166
+ "trifluoroborates"
2167
+ ],
2168
+ "syn_smarts": "[#6;$(c),$(C=C);!$(C=C-[#6]=[#6,#7,#8,#16]):101]-[Cl,Br,I].[#6;$(c),$(C=C),$(C#C),$(C(=O)-[#6]),$(C(F)(F)F),$(C);!$(C(=O)-[#7,#8,#16]);!$(C-[#6]=[#6,#7,#8,#16]):102]-[#5;-](F)(F)F>>[#6:101]-[#6:102]",
2169
+ "tags": [
2170
+ "Suzuki",
2171
+ "C-C bond formation",
2172
+ "C-C",
2173
+ "trifluoroborate"
2174
+ ],
2175
+ "tier": 1
2176
+ },
2177
+ "tetrahydroindole-1": {
2178
+ "allow_multiple_products": true,
2179
+ "description": "Tetrahydroindole synthesis from a cyclohexanone, 2-OH ketone and a primary amine.",
2180
+ "ld_data": {
2181
+ "display_smarts": "O=C-1-C-C-C-C-C-1.[#6:101]-C(-O)-C(=O)-[#6:102].[#7]-[#6:103]>>C=1-2-N(-[#6:103])-C(-[#6:102])=C(-[#6:101])-C=1-C-C-C-C-2"
2182
+ },
2183
+ "long_name": "Tetrahydroindole synthesis",
2184
+ "retro_smarts": "[c:8]12[C:1][C:2][C:3][C:4][c:9]1[c:10](-[#6:5])[c:11](-[#6:6])[n:12](-!@[#6:7])2>>[C:8](=O)1[C:1][C:2][C:3][C:4][C:9]1.[#6:5]-[C;H1:10](-[O;H1])[C:11](=O)-[#6:6].[N;H2:12]-[#6:7]",
2185
+ "rhs_classes": [
2186
+ "cyclohexanones",
2187
+ "ketones-2OH",
2188
+ "amines-prim"
2189
+ ],
2190
+ "syn_smarts": "[#6:1](=O)1-[C:2]-[C:3]-[C:4]-[C:5]-[#6;H2:6]-1.[#6;!$([#6]=[#6,#7,#8,#16]):101]-[#6;H1:8](-[O;H1])-[#6:9](=O)-[#6;!$([#6]=[#6,#7,#8,#16]):102].[#7;H2:11]-[#6;!$([#6]=[#6,#7,#8,#16]):103]>>[#6:1]12:[#7;H0:11](-[#6:103]):[#6:9](-[#6:102]):[#6;H0:8](-[#6:101]):[#6;H0:6]:1-[#6:5]-[#6:4]-[#6:3]-[#6:2]-2",
2191
+ "tags": [
2192
+ "heterocycle formation",
2193
+ "heterocycle",
2194
+ "tetrahydroindole"
2195
+ ],
2196
+ "tier": 2
2197
+ },
2198
+ "tetrazole-1": {
2199
+ "description": "Tetrazole from nitrile and alkyl halide; first regioisomer.",
2200
+ "ld_data": {
2201
+ "display_smarts": "[#6:101]-C#N.[#6:102]-[Br]>>[#6:102]-N-1-N=C(-[#6:101])-N=N-1"
2202
+ },
2203
+ "long_name": "2,5-disubstituted tetrazole synthesis",
2204
+ "retro_smarts": "[C;!$(C=[C,N,O,S]):2]-!@[#7]1:[#7:4]:[#6:1](-!@[#6;!$(C=[C,N,O,S]);!$(C-[N,O,S]):3]):[#7]:[#7]:1>>[#6:3]-[#6:1]#[#7:4].[C:2]-Br",
2205
+ "rhs_classes": [
2206
+ "nitriles",
2207
+ "halides-primsec"
2208
+ ],
2209
+ "syn_smarts": "[#6;!$(C=[C,N,O,S]);!$(C-[N,O,S]):101]-[#6:1]#[#7].[C;!$(C=[C,N,O,S]):102]-[Cl,Br,I]>>[#6:102]-[#7]1-[#7]=[#6:1](-[#6:101])-[#7]=[#7]-1",
2210
+ "tags": [
2211
+ "heterocycle formation",
2212
+ "heterocycle",
2213
+ "tetrazole"
2214
+ ],
2215
+ "tier": 1
2216
+ },
2217
+ "tetrazole-2": {
2218
+ "description": "Tetrazole from nitrile and alkyl halide; second regioisomer.",
2219
+ "ld_data": {
2220
+ "display_smarts": "[#6:101]-C#N.[#6:102]-[Br]>>[#6:102]-N-1-C(-[#6:101])=N-N=N-1"
2221
+ },
2222
+ "long_name": "1,5-disubstituted tetrazole synthesis",
2223
+ "retro_smarts": "[C;!$(C=[C,N,O,S]):4]-!@[#7]1:[#6:1](-!@[#6;!$(C=[C,N,O,S]);!$(C-[N,O,S]):3]):[#7:2]:[#7]:[#7]:1>>[#6:3]-[#6:1]#[#7:2].[C:4]-Br",
2224
+ "rhs_classes": [
2225
+ "nitriles",
2226
+ "halides-primsec"
2227
+ ],
2228
+ "syn_smarts": "[#6;!$(C=[C,N,O,S]);!$(C-[N,O,S]):101]-[#6:1]#[#7:2].[C;!$(C=[C,N,O,S]):102]-[Cl,Br,I]>>[#6:102]-[#7]1-[#6:1](-[#6:101])=[#7:2]-[#7]=[#7]-1",
2229
+ "tags": [
2230
+ "heterocycle formation",
2231
+ "heterocycle",
2232
+ "tetrazole"
2233
+ ],
2234
+ "tier": 1
2235
+ },
2236
+ "tetrazole-3": {
2237
+ "description": "Synthesis of a terminal tetrazole from a nitrile.",
2238
+ "ld_data": {
2239
+ "display_smarts": "[#6:101]-C#N>>[#6:101]-C-1=N-N-N=N-1"
2240
+ },
2241
+ "long_name": "Synthesis of a terminal tetrazole from a nitrile and sodium azide",
2242
+ "retro_smarts": "[#6;!$(C=[C,N,O,S]);!$(C-[N,O,S]):101]-[#6:2]:1:[#7:3]:[n;H1;D2]:[n;D2]:[n;D2]:1>>[#6:101]-[C:2]#[N:3]",
2243
+ "rhs_classes": [
2244
+ "nitriles"
2245
+ ],
2246
+ "syn_smarts": "[#6;!$(C=[C,N,O,S]);!$(C-[N,O,S]):101]-[C:2]#[N:3]>>[#6:101]-[C:2]1=[N:3]-[N;H1]-N=N-1",
2247
+ "tags": [
2248
+ "heterocycle formation",
2249
+ "heterocycle",
2250
+ "tetrazole",
2251
+ "transformation"
2252
+ ],
2253
+ "tier": 1
2254
+ },
2255
+ "thiazole-1": {
2256
+ "description": "Hantzsch thiazole synthesis from a thioamide and alpha-halo ketone.",
2257
+ "ld_data": {
2258
+ "display_smarts": "[#7]-C(=[#16])-[#6:101].[#6:102]-C(=O)-C-Cl>>N-1=C(-[#6:101])-S-C=C(-[#6:102])-1"
2259
+ },
2260
+ "long_name": "Hantzsch 2,5-disubstituted thiazole synthesis",
2261
+ "retro_smarts": "[#6;$([c;H1]),$([c;H0](n)(c)[#6;!$([c;R2]):2]):1]2[n:6][c:3](-!@[#6;!$([#6]=[#7,#8,#16]):5])[s;X2:7][c;$([#6;H0]-[#6;!$(C=[C,N,O,S])]),$([#6;H1]):4]2>>[#7;H2:6]-[#6:3](-[#6:5])=[#16:7].[#6:1](=O)-[#6:4]-Cl",
2262
+ "rhs_classes": [
2263
+ "thioamides",
2264
+ "ketones-2halo"
2265
+ ],
2266
+ "syn_smarts": "[#7;H2:1]-[#6:2](=[#16;X1:3])-[#6;!$([#6]=[#7,#8,#16]):101].[#6;$([#6;H1]-[#6;H1,H2:7]),$([#6;H0](-[#6;!$([c;R2]):102])-[#6;H1,H2:7]):6](=O)-[#6;$([#6;H2]),$([#6;H1](-C=O)-[#6;!$(C=[C,N,O,S])]):7]-[F,Cl,Br,I]>>[#7;H0:1]1=[#6:2](-[#6:101])-[#16:3]-[#6:7]=[#6:6]-1",
2267
+ "tags": [
2268
+ "Hantzsch",
2269
+ "heterocycle formation",
2270
+ "heterocycle",
2271
+ "thiazole"
2272
+ ],
2273
+ "tier": 1
2274
+ },
2275
+ "thiazole-2": {
2276
+ "description": "Hantzsch thiazole synthesis from thioformamide and an alpha-halo ketone.",
2277
+ "ld_data": {
2278
+ "display_smarts": "[#6:101]-C(=O)-C-Cl>>N-1=C-S-C=C(-[#6:101])-1"
2279
+ },
2280
+ "long_name": "Hantzsch 5-substituted thiazole synthesis",
2281
+ "retro_smarts": "[c;$([c;H1]),$([c;H0](n)(c)[#6;!$([c;R2]):2]):1]2n[c;H1][s;X2][c;$([#6;H0]-[#6;!$(C=[C,N,O,S])]),$([#6;H1]):4]2>>[#6:1](=O)-[#6:4]-Cl",
2282
+ "rhs_classes": [
2283
+ "ketones-2halo"
2284
+ ],
2285
+ "syn_smarts": "[#6;$([#6;H1]),$([#6;H0](-[#6;H1,H2:7])-[#6;!$([c;R2]):101]):6](=O)-[#6;$([#6;H2]),$([#6;H1](-[#6]=O)-[#6;!$(C=[C,N,O,S])]):7]-[F,Cl,Br,I]>>[#7]1=[#6]-[#16;X2]-[#6:7]=[#6:6]-1",
2286
+ "tags": [
2287
+ "Hantzsch",
2288
+ "heterocycle formation",
2289
+ "heterocycle",
2290
+ "thiazole",
2291
+ "transformation"
2292
+ ],
2293
+ "tier": 1
2294
+ },
2295
+ "thioether-1": {
2296
+ "description": "Thioether synthesis from styrenes and thiols.",
2297
+ "ld_data": {
2298
+ "display_smarts": "[#6]=C-C-1=C-C=C-C=C-1.[#6:101]-[#16]>>[#6:101]-S-C-C-C-1=C-C=C-C=C-1"
2299
+ },
2300
+ "long_name": "Thioether synthesis with styrene",
2301
+ "retro_smarts": "[#6:10]-[#16;X2:9]-!@[C;$([C;H2]),$([C;H1](-[#16:9])(-[C:7]-c)-[#6;!$(C=[C,N,O,S]);!$(C#[C,N])]):8]-[C;$([C;H2]),$([C;H1](-[c:1])(-[C:8]-[#16:9])-[#6;!$(C=[C,N,O,S]);!$(C#[C,N])]):7]-[c:1]>>[#6:8]=[#6:7]-[c:1].[#6:10]-[#16:9]",
2302
+ "rhs_classes": [
2303
+ "styrenes",
2304
+ "thiols"
2305
+ ],
2306
+ "syn_smarts": "[C;$([C;H2]),$([C;H1]-[#6;!$(C=[C,N,O,S]);!$(C#[C,N])]):8]=[C;$([C;H1]),$([C;H0](-[c:1])-[#6;!$(C=[C,N,O,S]);!$(C#[C,N])]):7]-[c:1].[#6:101]-[#16;D1;H1;!$([#16]-[#6]=[C,N,O,S]):9]>>[#6:101]-[#16;H0:9]-[C:8]-[C:7]-[c:1]",
2307
+ "tags": [
2308
+ "thioether"
2309
+ ],
2310
+ "tier": 1
2311
+ },
2312
+ "thioether-2": {
2313
+ "description": "Thioether synthesis from halides and thiols.",
2314
+ "ld_data": {
2315
+ "display_smarts": "[#6:101]-[Br].[#6:102]-[#16]>>[#6:102]-[#16]-[#6:101]"
2316
+ },
2317
+ "long_name": "Thioether synthesis with aryl or alkyl halides",
2318
+ "retro_smarts": "[#6;!$([#6]=[#6,#7,#8,#16]);!$([#6](-[#6])(-[#6])-[#6]):1]-!@[#16;X2:3]-[#6;!$([#6]=[#6,#7,#8,#16]):2]>>[#6:1]-Br.[#6:2]-[#16:3]",
2319
+ "rhs_classes": [
2320
+ "halides-aryl-primsec",
2321
+ "thiols"
2322
+ ],
2323
+ "syn_smarts": "[#6;!$([#6]=[#6,#7,#8,#16]);!$([#6](-[#6])(-[#6])-[#6]):101]-[Cl,Br,I].[#6;!$([#6]=[#6,#7,#8,#16]):102]-[#16;X2;H1:3]>>[#6:101]-[#16;H0:3]-[#6:102]",
2324
+ "tags": [
2325
+ "thioether"
2326
+ ],
2327
+ "tier": 1
2328
+ },
2329
+ "thiourea-1": {
2330
+ "description": "Thiourea synthesis from thioisocyanates and primary or secondary amines.",
2331
+ "ld_data": {
2332
+ "display_smarts": "[#6:101]-N=C=S.[#6:102]-[#7]>>[#6:102]-N-C(=S)-N-[#6:101]"
2333
+ },
2334
+ "long_name": "Thiourea synthesis from isocyanates",
2335
+ "retro_smarts": "[#6;!$([#6]=[#7,#8,#16]):101]-[N;H1:2]-[C;!R:3](=[S;X1:4])-!@[N;$([N;H0](-C=S)(-[#6;!$([#6]=[C,N,O,S]):103])-[#6;!$([#6]=[C,N,O,S]):102]),$([N;H1](-C=S)-[#6;!$([#6]=[C,N,O,S]):102]):5]>>[#6:101]-[N;H0:2]=[C:3]=[S;X1:4].[N:5]",
2336
+ "rhs_classes": [
2337
+ "thioisocyanates",
2338
+ "amines-primsec"
2339
+ ],
2340
+ "syn_smarts": "[#6;!$([#6]=[#7,#8,#16]):101]-[N:2]=[C;!R]=[S;X1].[N;$([N;H1](-[#6;!$([#6]=[C,N,O,S]):103])-[#6;!$([#6]=[C,N,O,S]):102]),$([N;H2]-[#6;!$([#6]=[C,N,O,S]):102]):3]>>[#6:101]-[N:2]-C(=S)-[N:3]",
2341
+ "tags": [
2342
+ "thiourea"
2343
+ ],
2344
+ "tier": 1
2345
+ },
2346
+ "urea-1": {
2347
+ "description": "Urea synthesis from isocyanates and primary or secondary amines.",
2348
+ "ld_data": {
2349
+ "display_smarts": "[#6:101]-N=C=O.[#6:102]-[#7]>>[#6:102]-N-C(=O)-N-[#6:101]"
2350
+ },
2351
+ "long_name": "Urea synthesis from isocyanates and primary or secondary amines",
2352
+ "retro_smarts": "[#6;!$([#6]=[#7,#8,#16]):101]-[N;H1:2]-[C;!R:3](=[O;X1:4])-!@[N;$([N;H0](-C=O)(-[#6;!$([#6]=[C,N,O,S]):103])-[#6;!$([#6]=[C,N,O,S]):102]),$([N;H1](-C=O)-[#6;!$([#6]=[C,N,O,S]):102]):5]>>[#6:101]-[N:2]=[C:3]=[O;X1:4].[N:5]",
2353
+ "rhs_classes": [
2354
+ "isocyanates",
2355
+ "amines-primsec"
2356
+ ],
2357
+ "syn_smarts": "[#6;!$([#6]=[#7,#8,#16]):101]-[N:2]=[C;!R]=[O;X1].[N;$([N;H1](-[#6;!$([#6]=[C,N,O,S]):103])-[#6;!$([#6]=[C,N,O,S]):102]),$([N;H2]-[#6;!$([#6]=[C,N,O,S]):102]):3]>>[#6:101]-[N:2]-C(=O)-[N:3]",
2358
+ "tags": [
2359
+ "urea"
2360
+ ],
2361
+ "tier": 1
2362
+ },
2363
+ "urea-2": {
2364
+ "description": "Urea synthesis from primary or secondary amines and primary or secondary amines.",
2365
+ "ld_data": {
2366
+ "display_smarts": "[#6:101]-[#7].[#6:102]-[#7]>>[#6:102]-N-C(=O)-N-[#6:101]"
2367
+ },
2368
+ "long_name": "Urea synthesis from two primary or secondary amines",
2369
+ "retro_smarts": "[#6;!$([#6]=[#7,#8,#16]):101]-[N;$([N;H1](-C=O)-[#6;!$([#6]=[#6,#7,#8,#16]):101]),$([N;H0](-C=O)(-[#6;!$([#6]=[#6,#7,#8,#16]):103])-[#6;!$([#6]=[#6,#7,#8,#16]):101]):2]-!@C(=O)-[N;$([N;H0](-[#6;!$([#6]=[C,N,O,S]):104])-[#6;!$([#6]=[C,N,O,S]):102]),$([N;H1]-[#6;!$([#6]=[C,N,O,S]):102]):3]-[#6;!$([#6]=[C,N,O,S]):102]>>[#6:101]-[N:2].[N:3]-[#6:102]",
2370
+ "rhs_classes": [
2371
+ "amines-primsec",
2372
+ "amines-primsec"
2373
+ ],
2374
+ "syn_smarts": "[#6;!$([#6]=[C,N,O,S]):101]-[N;$([N;H1](-[#6;!$([#6]=[C,N,O,S]):101])-[#6;!$([#6]=[C,N,O,S]):103]),$([N;H2]-[#6;!$([#6]=[C,N,O,S]):101]):2].[#6;!$([#6]=[C,N,O,S]):102]-[N;$([N;H1](-[#6;!$([#6]=[C,N,O,S]):102])-[#6;!$([#6]=[C,N,O,S]):104]),$([N;H2]-[#6;!$([#6]=[C,N,O,S]):101]):3]>>[#6:101]-[N;$([N;H1](-C=O)-[#6:101]),$([N;H0](-C=O)(-[#6:103])-[#6:101]):2]-C(=O)-[N;$([N;H1](-C=O)-[#6:102]),$([N;H0](-C=O)(-[#6:104])-[#6:102]):3]-[#6:102]",
2375
+ "tags": [
2376
+ "urea"
2377
+ ],
2378
+ "tier": 1
2379
+ },
2380
+ "vinyl-reduction": {
2381
+ "description": "Reduction of vinyl groups.",
2382
+ "ld_data": {
2383
+ "display_smarts": "[#6:101]/C=C/[#6:201]>>[#6:101]-C-C-[#6:201] |$;;;Aryl_p;;;;Aryl_p$|"
2384
+ },
2385
+ "long_name": "Reduction of arylvinyl groups",
2386
+ "retro_smarts": "[c:101]-[C;$([C;H2]),$([C;H1](-[C;!$([#6]=[C,N,O,S]):3])(-[#6;!$([#6]=[C,N,O,S])])-[c:101]):2]-[C;$([C;H3]),$([C;H2](-[C;!$([#6]=[C,N,O,S]):2])-[c:102]),$([C;H1](-[C;!$([#6]=[C,N,O,S]):2])(-[#6;!$([#6]=[C,N,O,S])])-[c:102]):3]>>[c:101]-[C:2]=[C:3]",
2387
+ "syn_smarts": "[c:101]-[C;$([C;H1]),$([C;H0](-[#6;!$([#6]=[C,N,O,S])])-[c:101]):2]=[C;$([C;H2]),$([C;H1]-[c:102]),$([C;H0](-[#6;!$([#6]=[C,N,O,S])])-[c:102]):3]>>[c:101]-[C:2]-[C:3]",
2388
+ "tags": [
2389
+ "reduction",
2390
+ "arylvinyl",
2391
+ "vinyl",
2392
+ "transformation"
2393
+ ],
2394
+ "tier": 1
2395
+ },
2396
+ "yamaguchi": {
2397
+ "description": "Yamaguchi macrolactonization.",
2398
+ "ld_data": {
2399
+ "display_smarts": "[#8]-C-C-C-C-C(-[#8])=O>>O=C-1-C-C-C-C-O-1 |Sg:n:12:n:ht,Sg:n:2:n:ht|"
2400
+ },
2401
+ "long_name": "Yamaguchi macrolactonization",
2402
+ "retro_smarts": "[#6:4][#6:5]-[C;R:6](=[O:7])-[O:1]-[#6;!$([#6](-[#8])-[#8]):2][#6:3]>>([O;H1:1]-[#6:2][#6:3].[#6:4][#6:5]-[C:6](=[O:7])-[O;H1])",
2403
+ "syn_smarts": "([O;H1:1]-[#6;!$([#6](-[#8])-[#8]):2][#6:3].[#6:4][#6:5]-[C;!R:6](=[O:7])-O)>>[#6:4]-[#6:5]-[C:6](=[O:7])-[O;H0:1]-[#6:2]-[#6:3]",
2404
+ "tags": [
2405
+ "Yamaguchi",
2406
+ "esterification",
2407
+ "lactone",
2408
+ "macrolactonization",
2409
+ "transformation",
2410
+ "intramolecular"
2411
+ ],
2412
+ "tier": 1
2413
+ }
2414
+ }