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Synthesis 2018; 50(10): 1979-1990
DOI: 10.1055/s-0036-1591768
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© Georg Thieme Verlag Stuttgart · New York

[3+2] Cycloaddition of Trifluoromethylated N-Acylhydrazones with Maleates: Synthesis of Trifluoromethylated Pyrazolidines

Lan Wen
a   College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu 730070, P. R. of China   Email: huyl@nwnu.edu.cn
,
Danfeng Huang*
a   College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu 730070, P. R. of China   Email: huyl@nwnu.edu.cn
,
Ke-Hu Wang
a   College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu 730070, P. R. of China   Email: huyl@nwnu.edu.cn
,
Yuxiang Wang
a   College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu 730070, P. R. of China   Email: huyl@nwnu.edu.cn
,
Lili Liu
a   College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu 730070, P. R. of China   Email: huyl@nwnu.edu.cn
,
Zheng Yang
a   College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu 730070, P. R. of China   Email: huyl@nwnu.edu.cn
,
Yingpeng Su
a   College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu 730070, P. R. of China   Email: huyl@nwnu.edu.cn
,
Yulai Hu*
a   College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu 730070, P. R. of China   Email: huyl@nwnu.edu.cn
b   State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China
› Author AffiliationsThis work was supported by the National Natural Science Foundation of China (Grant No. 21662030; 21462037). We also thank the Key Laboratory Polymer Materials of Gansu Province (Northwest Normal University), Key Laboratory of Eco-Environment-Related Polymer Materials (Ministry of Education, China), and State Key Laboratory of Applied Organic Chemistry (Lanzhou University) for financial support.
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Publication History

Received: 22 November 2017

Accepted after revision: 02 February 2018

Publication Date:
08 March 2018 (online)

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Abstract

An efficient [3+2] cycloaddition reaction of trifluoromethylated N-acylhydrazones with dimethyl maleate has been developed under basic conditions. This protocol provides an easy access to potentially bioactive trifluoromethylated pyrazolidines in moderate to excellent yields. It also illustrates that the trifluoromethylated N-acylhydrazones are useful trifluoromethyl building blocks for the synthesis of trifluoromethylated N-heterocycles.

Key words

trifluoromethylated N-acylhydrazones - maleates - pyrazolidines - cycloaddition - trifluoromethyl building blocks

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591768.
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