“All-water” chemistry of tandem N-alkylation–reduction–condensation for synthesis of N-arylmethyl-2-substituted benzimidazoles

Literature Information

Publication Date 2012-10-04
DOI 10.1039/C2GC36377A
Impact Factor 10.182
Authors

Damodara N. Kommi, Dinesh Kumar, Rohit Bansal, Rajesh Chebolu, Asit K. Chakraborti


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Abstract

A water-assisted tandem N-alkylation–reduction–condensation process has been devised as a new synthetic route for the one-pot synthesis of N-arylmethyl-2-substituted benzimidazoles. Water plays the crucial and indispensable role through hydrogen bond mediated ‘electrophile–nucleophile dual activation’ in promoting selective N-monobenzylation of o-nitroanilines as an alternative to the transition metal-based chemistry for C–N bond formation (amination) and forms the basis of disposing the substituents on the benzimidazole moiety in regiodefined manner. Water also exerts a beneficial effect in the condensation of N-monobenzylated o-phenylenediamines with aldehydes. The water-assisted C–N bond formation chemistry led to metal/base-free synthesis of N-monobenzylated o-nitroanilines and N-monobenzylated o-phenylenediamines. The indispensable/advantageous role of water in the various stage of the N-alkylation–reduction–condensation process exemplifies an ‘all-water’ chemistry for the synthesis of N-arylmethyl-2-substituted benzimidazoles.

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