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Paper | Regular issue | Vol 100, No. 8, 2020, pp.1189-1217
Published online, 9th June, 2020
DOI: 10.3987/COM-20-14278
Synthesis of Dimethoxy Activated Benzimidazoles and Bisbenzimidazoles

Mahiuddin Alamgir, Glenn C. Condie, Vesna Martinovic, Joanne Wood, Hayat Sholihin, Paul K. Bowyer, Naresh Kumar, and David StC. Black*

*School of Chemistry, The University of New South Wales, Sydney 2052, Australia

Abstract

A range of 2-substituted-4,6-dimethoxy activated benzimidazoles and 2,2'-bisbenzimidazoles have been synthesized from 2-aminoanilide derivatives under acidic conditions. The starting materials were prepared either by acylation from 3,5-dimethoxyaniline followed by nitration, or by acylation from 3,5-dimethoxy-2-nitroaniline. The 2-nitroanilides were then reduced by palladium catalyzed reaction with hydrazine and subsequent acid catalyzed cyclization giving the corresponding 4,6-dimethoxybenzimidazoles and 4,6-dimethoxy-2,2'-bisbenzimidazoles. In addition, 2-phenyl-4,5,6-trimethoxybenzimidazole has been synthesized using a similar procedure.