Organic Letters 2006-10-01

Novel alternative for the N-S bond formation and its application to the synthesis of benzisothiazol-3-ones.

Arkaitz Correa, Imanol Tellitu, Esther Dom__nguez, Raul SanMartin

Index: Org. Lett. 8(21) , 4811-3, (2006)

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Abstract

[reaction: see text] 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 N-S bond.