Synthesis of 2-amino-1,4-benzodiazepin-5-ones from 2-nitrobenzoic acid and α-aminonitriles

Abstract

Condensation of -aminonitriles with 2-nitrobenzoyl chloride gives the corresponding Schiff bases, which furnish, upon reduction with Zn, the corresponding 2-amino-3,4-dihydro-5H-1,4benzodiazepin-5-ones. However, reduction of the Schiff base obtained from the condensation of 1-aminocyclohexanecarbonitrile with 2-nitrobenzaldehyde gives the methanol adduct of 2aminobenzaldehyde trimer.