Synthesis 2018; 50(09): 1907-1913
DOI: 10.1055/s-0036-1591909
paper
© Georg Thieme Verlag Stuttgart · New York

Tin-Powder-Promoted One-Pot Synthesis of 5-Trifluoromethyl-5-aryl-3-methylidenepyrrolidin-2-ones

Authors

  • Ke-Hu Wang*

    a   College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, 730070, P. R. of China   Email: wangkh@nwnu.edu.cn   Email: huyl@nwnu.edu.cn
  • Jianglong Wang

    a   College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, 730070, P. R. of China   Email: wangkh@nwnu.edu.cn   Email: huyl@nwnu.edu.cn
  • Yalin Wang

    a   College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, 730070, P. R. of China   Email: wangkh@nwnu.edu.cn   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: wangkh@nwnu.edu.cn   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: wangkh@nwnu.edu.cn   Email: huyl@nwnu.edu.cn
  • Ying Fu

    a   College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, 730070, P. R. of China   Email: wangkh@nwnu.edu.cn   Email: huyl@nwnu.edu.cn
  • Zhengyin Du

    a   College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, 730070, P. R. of China   Email: wangkh@nwnu.edu.cn   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: wangkh@nwnu.edu.cn   Email: huyl@nwnu.edu.cn
    b   State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China

We thank the National Natural Science Foundation of China (21462037, 21662030), the Key Laboratory Polymer Materials of Gansu Province (Northwest Normal University), the Key Laboratory of Eco-Environment-Related Polymer Materials, Ministry of Education, China, and the State Key Laboratory of Applied Organic Chemistry, Lanzhou University for financial support.
Further Information

Publication History

Received: 08 November 2017

Accepted after revision: 21 December 2017

Publication Date:
29 January 2018 (online)


Graphical Abstract

Abstract

A simple and efficient synthetic approach is reported for the synthesis of 5-trifluoromethyl-5-aryl-3-methylidenepyrrolidin-2-ones in moderate to excellent yields via an acid-catalyzed one-pot multicomponent reaction of aromatic trifluoromethyl ketones, acylhydrazines, and ethyl 2-(bromomethyl)acrylate promoted by tin powder. The protocol is operationally simple. The overall process involves allylation and cyclization of the intermediate of acylhydrazones.

Supporting Information