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Synthesis 2011(12): 1998-2002  
DOI: 10.1055/s-0030-1260037
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

N-Heterocyclic Carbene Catalyzed Cyclization Cascades of 3-Halopropenals and Arylnitroso Compounds to 2,3-Disubstituted Isoxazol-5(2H)-ones

Weijun Yao, Ming Bian, Gang Wang, Cheng Ma*
Department of Chemistry, Zhejiang University, 20 Yugu Road, Hangzhou 310027, P. R. of China
Fax: +86(571)87953375; e-Mail: mcorg@zju.edu.cn;
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Publication History

Received 14 March 2011
Publication Date:
10 May 2011 (online)

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Abstract

An NHC-catalyzed annulation reaction of 3-halopropenals with nitrosobenzene derivatives, providing access to 2,3-disubstituted isoxazol-5(2H)-ones under mild conditions is described. This procedure represents a metal-free approach to the alternative equivalent of β-acylvinyl anions for the formation of heterocyclic compounds.

Key words

carbenes - cyclization - heterocycles - tandem reaction - umpolung

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