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Synthesis 2007(18): 2791-2796
DOI: 10.1055/s-2007-983875
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
Further Information
Received
11 June 2007
Publication Date:
29 August 2007 (online)
Publication History
Publication Date:
29 August 2007 (online)
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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