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Synthesis 2012; 44(9): 1323-1328
DOI: 10.1055/s-0031-1289740
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of N-Sulfonylazetidin-2-imines via the Copper(I) Oxide Catalyzed Multicomponent Reaction of Alkynes, Sulfonyl Azides and Diimines under Solvent-Free Conditions

Xiaohu Yi
a   Department of Chemistry, Northeast Normal University, 5268 Renmin Street, 130024 Changchun, P. R. of China, Fax: +86(431)85099759   Email: bixh507@nenu.edu.cn   Email: liaopq774@nenu.edu.cn
,
Badru-Deen Barry
a   Department of Chemistry, Northeast Normal University, 5268 Renmin Street, 130024 Changchun, P. R. of China, Fax: +86(431)85099759   Email: bixh507@nenu.edu.cn   Email: liaopq774@nenu.edu.cn
,
Peiqiu Liao*
a   Department of Chemistry, Northeast Normal University, 5268 Renmin Street, 130024 Changchun, P. R. of China, Fax: +86(431)85099759   Email: bixh507@nenu.edu.cn   Email: liaopq774@nenu.edu.cn
,
Xihe Bi*
a   Department of Chemistry, Northeast Normal University, 5268 Renmin Street, 130024 Changchun, P. R. of China, Fax: +86(431)85099759   Email: bixh507@nenu.edu.cn   Email: liaopq774@nenu.edu.cn
b   State Key Laboratory of Fine Chemicals, School of Chemical Engineering, University of Technology, Dalian 116012, P. R. of China
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Publication History

Received: 30 January 2012

Accepted after revision: 01 March 2012

Publication Date:
05 April 2012 (online)

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Abstract

N-Sulfonylazetidin-2-imines are synthesized efficiently via three-component reactions of sulfonyl azides, terminal alkynes, and carbodiimides using copper(I) oxide as an inexpensive and eco-friendly catalyst under solvent-free conditions, without the need for an additional base or ligand. The same method is applied to the preparation of an azetidin-2-ylidene derivative using a 1,2-diimine as the nucleophile.

Key words

N-sulfonylazetidin-2-imines - multicomponent reaction - copper(I) oxide - solvent-free - sulfonyl azides

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