Premium
Ring transformation of 4‐amino‐1 H ‐1,5‐benzodiazepine‐3‐carbonitrile and ethyl 4‐amino‐1 H ‐1,5‐benzodiazepine‐3‐carboxylate into benzimidazole derivatives with amines
Author(s) -
Aotsuka Tomoji,
Okamoto Yoshihisa,
Takagi Kaname,
HubertHabart Michel
Publication year - 1991
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.5570280254
Subject(s) - chemistry , ethylamine , methylamine , benzodiazepine , hydrochloride , medicinal chemistry , diazepine , ring (chemistry) , benzimidazole , amine gas treating , carboxylate , stereochemistry , organic chemistry , biochemistry , receptor
The ring contraction of 4‐ammo‐1 H ‐1,5‐benzodiazepine‐3‐carbonitrile hydrochloride 1 and ethyl 4‐amino‐1 H ‐1,5‐benzodiazepine‐3‐carboxylate hydrochloride 2 with aromatic primary amines into benzimidazole derivatives 3 and 4 was readily accomplished by heating in methanol. Benzodiazepine 1 also reacted with methylamine and ethylamine at about 40° to give ring‐opened amine adducts 7 which were recyclized to 1 with hydrochloric acid.