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Issue 10, 2009
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Water mediated chemoselective synthesis of 1,2-disubstituted benzimidazoles using o-phenylenediamine and the extended synthesis of quinoxalines

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Abstract

By applying water as the reaction medium, the one-pot synthesis of 1,2-disubstituted benzimidazoles has been achieved in excellent efficiency and selectivity at room temperature viatrimethylsilyl chloride promoted reaction of o-phenylenediamine with aldehyde. This green catalyst system has also been successfully extended to the synthesis of quinoxalines via the reaction of o-phenylenediamine with α-bromoketone. Water displayed a specific functionality in mediating the selectivity, and remarkable advantages over organic solvents in terms of yields as well as in the work up procedure of the reactions.

Graphical abstract: Water mediated chemoselective synthesis of 1,2-disubstituted benzimidazoles using o-phenylenediamine and the extended synthesis of quinoxalines

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Publication details

The article was received on 29 May 2009, accepted on 14 Jul 2009 and first published on 29 Jul 2009


Article type: Paper
DOI: 10.1039/B914286J
Citation: Green Chem., 2009,11, 1633-1637
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    Water mediated chemoselective synthesis of 1,2-disubstituted benzimidazoles using o-phenylenediamine and the extended synthesis of quinoxalines

    J. Wan, S. Gan, J. Wu and Y. Pan, Green Chem., 2009, 11, 1633
    DOI: 10.1039/B914286J

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