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Green Chem., 2009, 11, 1633 - 1637, DOI: 10.1039/b914286j

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

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 -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 image for this article (ID: b914286j)