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Synthesis 2002(2): 0185-0190
DOI: 10.1055/s-2002-19793
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Novel and Efficient Regiospecific Preparation of Arenesulfonamide Derivatives of 3,5-Diamino-1,2,4-triazole

Kelly Chibale*a, Jérôme Dauvergnea,, Paul G. Wyattb
a Department of Chemistry, University of Cape Town, Rondebosch 7701, South Africa
Fax: +27(21)6897499; e-Mail: chibale@science.uct.ac.za;
b Department of Medicinal Chemistry, GlaxoSmithKline Medicines Research Centre, Gunnels Wood Road, Stevenage, Herts, SG1 2NY, U.K.
Further Information

Publication History

Received 27 September 2001
Publication Date:
03 August 2004 (online)

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Abstract

A new simple and efficient procedure was designed for the regiospecific preparation of arenesulfonamide derivatives of 3,5-diamino-1,2,4-triazole 1 which are precursors of N-([1,2,4]triazolo[1,5-a]pyrimidin-2-yl)arenesulfonamides 2, an important family of herbicidal and antibacterial agents. The key feature of this procedure is the preparation of a wide range of compounds 1 on a large scale, in pure form and high yield without the need for any workup or the use of the highly hazardous hydrazine. This was made possible by a novel tandem reaction promoted by sulfuryl chloride to effect the formation of the triazole ring.

Key words

triazole ring formation - heterocycles - cyclizations - tandem reactions - herbicidal agents

1

Current address: Charterhouse Therapeutics Ltd., Department of Chemistry, Robert Robinson Laboratories, University of Liverpool, Liverpool L69 7ZD, UK.