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, Email: dongdw663nenu.edu.cn

Y. Liang, D. Dong, Y. Lu, Y. Wang, W. Pan, Y. Chai, Q. Liu, Synthesis, 2006, 3301-3304.

DOI: 10.1055/s-2006-950227

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Abstract

Upon treatment with aqueous sodium hydroxide in DMF, a range of chalcones underwent Michael addition reactions with nitroalkanes. The resulting adducts were reduced in situ with Zn/HCl (aq) to afford substituted Δ¹-pyrrolines in high yields after a cyclization.

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Key Words

chalcones, cyclizations, Michael additions, Zinc, hydrogenations, 1-pyrrolines

ID: J66-Y2006-3200

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

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