Volume 31, Issue 23
Preparative Organic Chemistry
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ChemInform Abstract: An Investigation of Imidazole and Oxazole Syntheses Using Aryl-Substituted TosMIC Reagents.

Joseph Sisko

Joseph Sisko

Synth. Chem. Dep., SmithKline Beecham Pharm., King of Prussia, PA 19406, USA

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Andrew J. Kassick

Andrew J. Kassick

Synth. Chem. Dep., SmithKline Beecham Pharm., King of Prussia, PA 19406, USA

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Mark Mellinger

Mark Mellinger

Synth. Chem. Dep., SmithKline Beecham Pharm., King of Prussia, PA 19406, USA

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John J. Filan

John J. Filan

Synth. Chem. Dep., SmithKline Beecham Pharm., King of Prussia, PA 19406, USA

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Andrew Allen

Andrew Allen

Synth. Chem. Dep., SmithKline Beecham Pharm., King of Prussia, PA 19406, USA

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Mark A. Olsen

Mark A. Olsen

Synth. Chem. Dep., SmithKline Beecham Pharm., King of Prussia, PA 19406, USA

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First published: 08 June 2010

Abstract

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ChemInform Abstract

Aryl-substituted tosylmethyl isocyanides readily undergo cycloadditions with a variety of imines generated in situ to give 1,4,5-trisubstituted as well as 1,4- and 4,5-disubstituted imidazoles in one pot. The method can easily accommodate chiral amines and aldehydes to generate products with excellent retention of chiral purity. The cycloaddition of the aryl-substituted tosylmethyl isocyanides with aldehydes generates smoothly oxazoles.

chemical structure image

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