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An Investigation of Imidazole and Oxazole Syntheses Using Aryl-Substituted TosMIC Reagents

Joseph Sisko*, Andrew J. Kassick, Mark Mellinger, John J. Filan, Andrew Allen and Mark A. Olsen

*SmithKline Beecham Pharmaceuticals, Synthetic Chemistry Department and Analytical Sciences Department, P.O. Box 1539, King of Prussia, Pennsylvania 19406, Email: joe.siskogsk.com

J. Sisko, A. J. Kassick, M. Mellinger, J. J. Filan, A. Allen, M. A. Olsen, J. Org. Chem., 2000, 65, 1516-1524.

DOI: 10.1021/jo991782l (free Supporting Information)


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Abstract

Mild and efficient protocols provide 1,4,5-trisubstituted and 1,4-/4,5-disubstituted imidazoles regioselectively in a single pot from aryl-substituted tosylmethyl isocyanide (TosMIC) reagents and imines generated in situ from virtually any aldehyde and amine. Mono- and disubstituted oxazoles can also prepared.

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Key Words

Van Leusen Imidazole Synthesis, Imidazoles


ID: J42-Y2000