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Issue 12, 2012
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“All-water” chemistry of tandem N-alkylation–reduction–condensation for synthesis of N-arylmethyl-2-substituted benzimidazoles

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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.

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

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Publication details

The article was received on 30 Aug 2012, accepted on 03 Oct 2012 and first published on 04 Oct 2012


Article type: Paper
DOI: 10.1039/C2GC36377A
Citation: Green Chem., 2012,14, 3329-3335
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    “All-water” chemistry of tandem N-alkylation–reduction–condensation for synthesis of N-arylmethyl-2-substituted benzimidazoles

    D. N. Kommi, D. Kumar, R. Bansal, R. Chebolu and A. K. Chakraborti, Green Chem., 2012, 14, 3329
    DOI: 10.1039/C2GC36377A

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