“All-water” chemistry for synthesis of N-arylmethyl-2-substituted benzimidazoles

Scientists from India have developed a tandem N-alkylation-reduction-condensation route to synthesize N-arylmethyl-2-substituted benzimidazoles.

1,2-Disubstituted benzimidazoles exhibit a broad range of biological activities, which make them a very popular synthetic target.  The regio-specific synthesis of these compounds is the main synthetic challenge, with the desired regioselectivity of the final compounds determined at the aryl-amination stage.  However, this traditionally requires a transition metal catalyst, expensive ligands and an appropriate base.

Graphical abstract for C2GC36377AIn this work, Asit Chakraborti and colleagues from the National Institute of Pharmaceutical Education and Research, Punjab, India, present a one-pot strategy to produce N-arylmethyl-2-substituted benzimidazoles in water.  The procedure does not require a transition metal catalyst or base, with water directing the regioselectivity of the reaction through hydrogen bond mediated ‘electrophile-nucleophile dual activation’.

Read the full article for free until the 4th December 2012!

“All-water” chemistry of tandem N-alkylation–reduction–condensation for synthesis of N-arylmethyl-2-substituted benzimidazoles, Damodara N. Kommi, Dinesh Kumar, Rohit Bansal, Rajesh Chebolu and Asit K. Chakraborti, Green Chem., 2012, DOI: 10.1039/C2GC36377A

You may also be interested in this article as well – free to access for two weeks:

Catalytic procedures for multicomponent synthesis of imidazoles: selectivity control during the competitive formation of tri- and tetrasubstituted imidazoles, Dinesh Kumar, Damodara N. Kommi, Narendra Bollineni, Alpesh R. Patel and Asit K. Chakraborti, Green Chem., 2012, 14, 2038-2049

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