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Reactions of 3‐acetyltropolone methyl ethers with o ‐phenylenediamine. Formation of cyclohepta[ b ][1,5]benzodiazepine
Author(s) -
Imafuku Kimiaki,
Yamane Akio,
Matsumura Hisashi
Publication year - 1981
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570180221
Subject(s) - chemistry , quinoxaline , tropone , medicinal chemistry , benzodiazepine , organic chemistry , biochemistry , receptor
Reactions of 3‐acetyltropolone methyl ethers with o ‐phenylenediamine are described. 3‐Acetyl‐2‐methoxytropone ( 2a ) with o ‐phenylenediamine in ethanol under reflux condition to afford 11‐hydroxy‐6‐methylcyclohepta[ b ][1,5]benzodiazepine ( 4 ), 10‐acetyl‐6 H ‐cyclohepta[ b ]quinoxaline ( 5 ), and 6‐acetyl‐5 H ‐cyclohepta[ b ]‐quinoxaline ( 6 ). The same reaction of 7‐acetyl‐2‐methoxytropone ( 2b ) gave 7‐acetyl‐2‐(2‐aminoanilino)‐tropone ( 3b ) besides 4, 5 , and 6. The compound 4 has a 1,4‐diazaheptalene skeleton.