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

Jie-Ping Wan; Shi-Feng Gan; Jian-Mei Wu; Yuanjiang Pan

doi:10.1039/B914286J

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Green Chemistry

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

Jie-Ping Wan , Shi-Feng Gan , Jian-Mei Wu and Yuanjiang Pan

Green Chem., 2009, 11, 1633-1637

DOI: 10.1039/B914286J
Received 29 May 2009, Accepted 14 Jul 2009
First published on the web 29 Jul 2009

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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 via trimethylsilyl 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.

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General experimental procedure, analytical data as well ascopies of 1H and 13C NMR spectra of all products. Copies of 1H NMRand ESI-MS+ spectra of 3a-d2
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Green Chemistry

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

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