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Announcement
Zenichi Yoshida (1925-2023)

Professor. Zenichi Yoshida,
a member of the Honorary Advisors of HETEROCYCLES (1975-1998),
has passed away on May 4, 2023 at the age of 97.
I deeply express my regret over his death.
Kunio Ogasawara
Editor
May 11, 2023
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■ 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
Abstract
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.
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