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Paper | Special issue | Vol 82, No. 1, 2010, pp.339-348
Published online, 22nd February, 2010
DOI: 10.3987/COM-10-S(E)4
Iodoarene-Mediated Cyclization of N-Methoxy-2-arylethanesulfonamides with Oxone

Yoshihide Ishiwata, Yuhsuke Suzuki, and Hideo Togo*

*Graduate School of Sciences, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan


Iodoarene-mediated cyclization of N-methoxy-2-arylethanesulfonamides with Oxone® was carried out to form the corresponding N-methoxy-3,4-dihydro-2,1-benzothiazine-2,2-dioxides in moderate to good yields in acetonitrile. In this reaction, reactive hypervalent iodine species, i.e., [(hydroxy)(tosyloxy)iodo]arenes, were formed in situ and reacted with N-methoxy-2-arylethanesulfonamides to form the corresponding N-methoxy-3,4-dihydro-2,1-benzothiazine-2,2-dioxides in an electrophilic manner on the aromatic ring. Ion-supported PhI could be also used for the same cyclization of N-methoxy-2- arylethanesulfonamides with Oxone® to provide N-methoxy-3,4-dihydro- 2,1-benzothiazine-2,2-dioxides in good to moderte yields. However, ion-supported PhI could not be reused for the same reaction. The same iodoarene-mediated cyclization of N-methoxy-3-phenylpropanamide and N-methoxy-4-phenylbutanamide with Oxone® was also carried out to form the corresponding N-methoxybenzolactams in moderate yields.