Acridizinium salts. Preparation from 1-(benzylic)-2-formyl and 1-(benzylic)-2-acetyl pyridinium bromides and ring-openings reactions with nucleophilic reagents

Abstract

Treatment of pyridine-2-carboxaldehyde or 2-acetyl pyridine with several benzylic bromides led to the corresponding 1-(benzylic)-2-formyl pyridinium bromides or 1-(benzylic)-2-acetyl pyridinium bromides, respectively. The use of MeOH as a solvent in the quaternizations of pyridine-2-carboxaldehyde with benzylic bromides ( or in one case benzyl chloride) led to the corresponding pyridinium hemiacetals. These salts were effectively cyclodehydrated to afford the corresponding acridizinium salts. The ring opening reactions of several of the acridizinium salts with hydroxide, oximes, primary amines and a hydrazine have been investigated. ©ARKAT USA, Inc.