SPECIALTOPIC	Synthesis 2006: 3301-3304   DOI: 10.1055/s-2006-950227
© 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;
Received 22 July 2006

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