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Synthesis 2008(13): 2073-2076  
DOI: 10.1055/s-2008-1067115
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Sulfonamides and 1,3-Oxazine-2,4-diones from Arylsulfonyl Isocyanates and Diketene

Abdolali Alizadeh*a, Nasrin Zohreha, Long-Guan Zhub
a Department of Chemistry, Tarbiat Modares University, P.O. Box 14115-175, Tehran 18716, Iran
b Chemistry Department, Zhejiang University, Hangzhou 310027, P. R. China
Fax: +98(21)88006544; e-Mail: abdol_alizad@yahoo.com; e-Mail: aalizadeh@modares.ac.ir;
Further Information

Publication History

Received 4 March 2008
Publication Date:
11 June 2008 (online)

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Abstract

An effective route to functionalized N 1-[(2,6-dimethyl-4-oxo-4H-pyran-3-yl)carbonyl]-1-arylsulfonamide and 3-(arylsulfonyl)-6-methyl-2H-1,3-oxazine-2,4(3H)-dione derivatives is described. This involves the reaction of arylsulfonyl isocyanates and diketene in the presence of N-heteroaromatic compounds such as 1,3,5-triazine, 1-methyl-1H-imidazole, or pyridine as catalyst. The reactive 1:1 zwitterions obtained from the addition of N-heteroaromatic compound to arylsulfonyl isocyanates were trapped by diketene to produce functionalized sulfonamide and 1,3-oxazine-2,4(3H)-dione derivatives.

Key words

arylsulfonyl isocyanate - catalytic reaction - diketene - N-heteroaromatic compounds - sulfonamides - zwitterions

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Crystallographic data for 5a have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 642465. Copies of the data may be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK (fax: +44 1223 33603 or e-mail: deposit@ccdc.cam.ac.uk).