One-pot synthesis of substituted isothiazol-3(2H)-ones: Intramolecular annulation of alpha-carbamoyl ketene-S,S-acetals via PIFA-Mediated N-S bond formation

A facile and efficient synthetic route towards; highly substituted isothiazol-3(2H)-ones 2 from readily available U.-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.