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Synthesis 2007(18): 2791-2796  
DOI: 10.1055/s-2007-983875
PAPER
© Georg Thieme Verlag Stuttgart · New York

One-Pot Synthesis of Substituted Isothiazol-3(2H)-ones: Intramolecular Annulation of α-Carbamoyl Ketene-S,S-acetals via PIFA-Mediated N-S Bond Formation

Jie Huanga, Yumei Lua, Baofu Qiua, Yongjiu Lianga, Nan Lia, Dewen Dong*a,b
a Department of Chemistry, Northeast Normal University, Changchun, 130024, P. R. of China
b Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, 130022, P. R. of China
Fax: +86(431)85098635; e-Mail: dongdw663@nenu.edu.cn;
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Publication History

Received 11 June 2007
Publication Date:
29 August 2007 (online)

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Abstract

A facile and efficient synthetic route towards highly substituted isothiazol-3(2H)-ones 2 from readily available α-carbamoyl ketene-S,S-acetals 1 is presented. The key step features the formation of an N-acylnitrenium ion, generated from the oxidization of substituted amides with the hypervalent iodine reagent phenyl­iodine(III) bis(trifluoroacetate) (PIFA), and its succeeding intra­molecular amidation to form a new N-S bond affording the title compounds.

Key words

α-carbamoyl ketene-S,S-acetals - isothiazol-3(2H)-ones - amidation - cyclization - hypervalent iodine reagent - trifluoroacetic acid