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

doi:10.1055/s-2006-950227

Subscribe to RSS

Please copy the URL and add it into your RSS Feed Reader.

https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synthesis 2006(19): 3301-3304
DOI: 10.1055/s-2006-950227

SPECIALTOPIC

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;

Further Information

Publication History

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

Abstract
Full Text
References

Buy Article Permissions and Reprints All articles of this category

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