Lithium Chloride Catalyzed Aza-Michael Addition of Pyrazoles to α,β-Unsaturated Imides

Hongyan Zhou; Xiancheng Xiang; Ben Ma; Ganggang Wang; Zhixia Zhang; Jingya Yang

doi:10.1055/s-0037-1611520

Synthesis, Table of Contents

Synthesis 2019; 51(16): 3142-3150
DOI: 10.1055/s-0037-1611520

paper

Lithium Chloride Catalyzed Aza-Michael Addition of Pyrazoles to α,β-Unsaturated Imides

Hongyan Zhou*

^aCollege of Science, Gansu Agricultural University, Lanzhou 730070, P. R. of China Email: zhouhy@gsau.edu.cn

^bCollege of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070, P. R. of China Email: yangjy@nwnu.edu.cn

,

Xiancheng Xiang

^bCollege of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070, P. R. of China Email: yangjy@nwnu.edu.cn

,

Ben Ma

^bCollege of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070, P. R. of China Email: yangjy@nwnu.edu.cn

,

Ganggang Wang

^bCollege of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070, P. R. of China Email: yangjy@nwnu.edu.cn

,

Zhixia Zhang

^aCollege of Science, Gansu Agricultural University, Lanzhou 730070, P. R. of China Email: zhouhy@gsau.edu.cn

,

Jingya Yang *

^bCollege of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070, P. R. of China Email: yangjy@nwnu.edu.cn

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Abstract

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Abstract

A lithium chloride catalyzed aza-Michael reaction of pyrazoles to α,β-unsaturated imides has been developed. A range of aromatic and aliphatic α,β-unsaturated imides are found to be suitable for the established method, providing the corresponding aza-Michael adducts in up to 93% yields. The inexpensive catalyst, good substrate tolerance, and ease of scale-up make this procedure highly practical.

Key words

Michael addition - α,β-unsaturated imides - pyrazoles - nitrogen heterocycles - regioselectivity

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References

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