Novel preparation of 2,1-benzothiazine derivatives from sulfonamides with [hydroxy(tosyloxy)iodo]arenes

Organic & Biomolecular Chemistry Pub Date: 2003-03-18 DOI: 10.1039/B301330H

Abstract

Cyclization of sulfonamides bearing an aromatic ring at the β-position with various organohypervalent iodine compounds was carried out to form the corresponding 2,1-benzothiazine derivatives. Among them, the cyclization effectively proceeded with [hydroxy(tosyloxy)iodo]arenes through ionic pathways. The same treatment of a sulfonamide bearing a 4-methoxyphenyl group at the β-position generated a spiro compound.

Graphical abstract: Novel preparation of 2,1-benzothiazine derivatives from sulfonamides with [hydroxy(tosyloxy)iodo]arenes
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