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Synthesis 2006(19): 3301-3304  
DOI: 10.1055/s-2006-950227
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart · New York

One-Pot Synthesis of Substituted Δ1-Pyrrolines through the Michael Addition of Nitroalkanes to Chalcones and Subsequent Reductive Cyclization in Aqueous Media

Yongjiu Liang, Dewen Dong*, Yumei Lu, Yan Wang, Wei Pan, Yanyan Chai, Qun Liu*
Department of Chemistry, Northeast Normal University, Changchun 130024, P. R. of China
Fax: +86(431)5098635; e-Mail: dongdw663@nenu.edu.cn;
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Publication History

Received 22 July 2006
Publication Date:
04 September 2006 (online)

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Abstract

A facile and efficient one-pot synthesis of substituted Δ1-pyrrolines in aqueous media has been developed. Upon treatment with aqueous sodium hydroxide in N,N-dimethylformamide, a range of chalcones underwent room temperature Michael addition reactions with nitroalkanes. The resulting adducts were directly reduced in situ with Zn/HCl (aq) and subsequently underwent an intramolecular cyclization, affording the corresponding substituted Δ1-pyrrolines in high yields.

Key words

chalcones - cyclizations - Michael additions - hydrogenations - pyrrolines