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 | Zendy

Aotsuka Tomoji | Zendy; Okamoto Yoshihisa | Zendy; Takagi Kaname | Zendy; HubertHabart Michel | Zendy

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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.

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