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Paper | Regular issue | Vol 100, No. 9, 2020, pp.1371-1404
Published online, 1st July, 2020
DOI: 10.3987/COM-20-14280
■ Reactivity of 4,6-Dimethoxy Activated Benzimidazoles

Mahiuddin Alamgir, Glenn C. Condie, Vesna Martinovic, Joanne Wood, Mohan Bhadbhade, Naresh Kumar, and David StC. Black*

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

Abstract

4,6-Dimethoxy-2-substituted-benzimidazoles undergo formylation, acylation, nitration and bromination at C7. The 7-carbaldehydes can be reduced to the corresponding hydroxymethyl compounds. Benzimidazole-2-carbaldehydes can be prepared by oxidation of 2-methyl- and 2-styryl-benzimidazoles. N-Methylation and N-allylation have also been investigated and lead to isomeric mixtures of 4,6- and 5,7-dimethoxybenzimidazoles. In general the nucleophilic capacity of the activated benzimidazoles is weaker than that of the related activated indoles, but still provides synthetic routes to a range of new heterocyclic structures.