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Synfacts 2007(1): 0021-0021  
DOI: 10.1055/s-2006-955749
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Benzothiazol-3-ones

Contributor(s): Victor Snieckus, Heiko Scharl
A. Correa, I. Tellitu*, E. Domínguez*, R. SanMartin
Euskal Herriko Unibertsitatea, Bilbao, Spain
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Publication History

Publication Date:
15 December 2006 (online)

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Significance

A convenient, new approach to benzoisothiazolones by using phenyliodine(III) bisfluoroacetate (PIFA) for the generation of the N-S bond is reported. The sequence involves ester-to-amide-group transformation followed by PIFA-mediated formation of an N-acylnitrenium ion which is intramolecularly trapped by S-H insertion. A limited scope of starting thiosalicylate substitution patterns was investigated.