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. 2010 Nov;5(11):1731-6.
doi: 10.1038/nprot.2010.132. Epub 2010 Oct 7.

A rapid and efficient route to benzazole heterocycles

Richard D Carpenter  1 , Mark J Kurth
Affiliations

A rapid and efficient route to benzazole heterocycles

Richard D Carpenter et al. Nat Protoc. 2010 Nov.

Abstract

This protocol describes a rapid, high-yielding, microwave-mediated route that affords benzazole heterocycles in high crude purity and represents a significant advancement toward an environmentally friendly reaction. The reaction of aryl isothiocyanates with o-nucleophilic anilines produces thiourea intermediates that, in the presence of a carbodiimide-functionalized resin, cyclize to benzazoles with the safe removal of one equivalent of hydrogen sulfide. This procedure takes ∼ 8.5 h to complete: 1-3 h for setup, 4.5 h for benzazole formation and 2 h for workup and purification.

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