Reactions of 3‐acetyltropolone methyl ethers with  o ‐phenylenediamine. Formation of cyclohepta[ b ][1,5]benzodiazepine | Zendy

Imafuku Kimiaki | Zendy; Yamane Akio | Zendy; Matsumura Hisashi | Zendy

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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.

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