ChemInform Abstract: Synthesis of 1,4‐Benzodiazepin‐3‐ones and 1,5‐Benzodiazocin‐4‐ones by Addition of Grignard Reagents to Derivatives of o‐Aminobenzonitrile.

Abstract

Derivatives of o-Aminobenzonitrile. -Addition of Grignard reagents to N-(α-haloacyl)-o-aminobenzonitrile results in formation of 2,5-disubstituted 1,4-benzodiazepin-3-ones. The method is also used to prepare higher homologues 1,5-benzodiazocin-4-ones (III). Addition of lithium reagents to N-(β-haloacyl)-o-aminobenzonitrile (X) gives 4,4-disubstituted quinazolines via Grob fragmentation. -(PETTERSSON, B.; RYDBECK, A.; BERGMAN*, J.; Org. Biomol.