Studies of seven-membered heterocycles. XXXII. Synthesis of N-unsubstituted 1H-1,4-benzodiazepines stabilized by intramolecular hydrogen bonding.

1 January 1990

journal article
research article
Published by Pharmaceutical Society of Japan in CHEMICAL & PHARMACEUTICAL BULLETIN

Vol. 38 (11) , 2919-2925
https://doi.org/10.1248/cpb.38.2919

Abstract

The stable N-unsubstituted 1H-1,4-benzodiazepines (12a-l) having a carbonyl group or its analogue at the 2- or 9-position were prepared from the 4-azidoquinolines (13a-l) by photoreaction in the presence of sodium methoxide. It is known that N-substituted 1H-1,4-benzodiazepines having no carbonyl group are too unstable to be isolated. Based on the spectral data, the benzodiazepines (12) isolated are assumed to be stabilized by intramolecular hydrogen bonding between the 1-NH hydrogen and the 2- or 9-carbonyl oxygen, thus allowing their isolation.

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