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Synthesis 2006(24): 4200-4204  
DOI: 10.1055/s-2006-950342
PAPER
© Georg Thieme Verlag Stuttgart · New York

First Example of Lewis Acid Catalyzed 3-Substituted 5-Arylidene-1-methyl-2-thiohydantoin Formation

Brian T. Gregg*, William G. Earley, Kathryn C. Golden, John F. Quinn, Dana A. Razzano, W. Martin Rennells
Albany Molecular Research, Inc., 21 Corporate Circle, PO Box 15098, Albany, NY 12212-5098, USA
Fax: +1(518)8674381; e-Mail: brian@albmolecular.com;
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Publication History

Received 15 June 2006
Publication Date:
02 November 2006 (online)

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Abstract

A survey of Lewis acids was conducted to facilitate the formation of arylidenethiohydantoins. The use of indium(III) trif­late shows significant advantages in facilitating this reaction. In most examples, the Lewis acid promoted catalysis gave shorter reaction times, higher conversion, and better purity profiles as compared to the traditional uncatalyzed reactions.

Key words

Lewis acids - catalysis - heterocycles - indium - condensation

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