Organic letters

Novel Alternative for the NS Bond Formation and Its Application to the Synthesis of Benzisothiazol-3-ones

A Correa, I Tellitu, E Domínguez, R SanMartin

Index: Correa, Arkaitz; Tellitu, Imanol; Dominguez, Esther; SanMartin, Raul Organic Letters, 2006 , vol. 8, # 21 p. 4811 - 4813

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Citation Number: 50

Abstract

The synthesis of a series of benzisothiazolone derivatives starting from the readily available methyl thiosalicylate is presented. The key cyclization step features the formation of a N- acylnitrenium ion, generated by the hypervalent iodine reagent PIFA, and its succeeding intramolecular trapping by the thiole moiety leading to the construction of the title compounds by formation of a new NS bond.