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 Huang; Yumei Lu; Baofu Qiu; Yongjiu Liang; Nan Li; Dewen Dong

doi:10.1055/s-2007-983875

PAPER

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 Huang^a, Yumei Lu^a, Baofu Qiu^a, Yongjiu Liang^a, Nan Li^a, 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;

Abstract

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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

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