Journal
HETEROCYCLES
Volume 82, Issue 1, Pages 339-348Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.3987/COM-10-S(E)4
Keywords
Iodoarene; N-Methoxy-2-arylethanesulfonamide; N-Methoxy-3,4-dihydro-2,1-benzothiazine-2,2-dioxide; Oxone (R); N-Methoxybenzolactam
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Funding
- Ministry of Education, Science, Sports and Culture of Japan [20550033]
- Chiba University
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Iodoarene-mediated cyclization of N-methoxy-2-arylethanesulfonamides with Oxone (R) 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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