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

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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