Novel alternative for the N-S bond formation and its application to the synthesis of benzisothiazol-3-ones.
[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.
Correa
Arkaitz
A
Departamento de Química Organica II, Facultad de Ciencia y Tecnología, Euskal Herriko Unibertsitatea, P.O. Box 644, 48080 Bilbao, Spain.
Tellitu
Imanol
I
Domínguez
Esther
E
SanMartin
Raul
R