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Quinazolines and 1,4‐benzodiazepines. LXXXV syntheses of 3‐substituted lmidazo[1,5‐a] [1,4]benzodiazepines
Author(s) -
Walser Armin,
Flynn Thomas,
Fryer R. Ian
Publication year - 1978
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.5570150411
Subject(s) - chemistry , carbanion , orthoester , amide , hydrolysis , acetal , organic chemistry , condensation , decarboxylation , nitrosation , medicinal chemistry , catalysis , physics , thermodynamics
1,4‐Benzodiazepines having a leaving group in the 2‐position were condensed with carbanions of 1,3‐dicarbonyl compounds. The products obtained were converted to the title compounds by a sequence of steps involving hydrolytic decarboxylation, nitrosation, catalytic hydrogenation and condensation with an orthoester or an amide acetal. Oxidative condensation of the enediamine 12 with a variety of aldehydes also led to imidazo‐benzodiazepines with various substituents in the 1‐position.