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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

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
› Author AffiliationsWe 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)

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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.

Key words

lactams - allylation - tin - trifluoromethyl ketones - acyl­hydrazines

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591909.
  • Supporting Information
 

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