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Synthesis 2017; 49(20): 4703-4710
DOI: 10.1055/s-0036-1588500
paper
© Georg Thieme Verlag Stuttgart · New York

An Intramolecular Cycloaddition Approach to Construct Polysubstituted Pyrrolidones from Alkynyl Carboxamides and PTSA

Xiao-Dan Han
a   Department of Applied Chemistry, Jiang Xi Academic of Sciences, Nanchang 330096, P. R. of China
,
Chuan-Qing Ren
b   Shaanxi Key Laboratory of Catalysis, School of Chemical & Environmental Science, Shaanxi, Sci-Tech University, Hanzhong, 723000 Shaanxi, P. R. of China   Email: kanxl433@nenu.edu.cn   Email: hjw19771985@163.com
,
Jian-Ping Fu
a   Department of Applied Chemistry, Jiang Xi Academic of Sciences, Nanchang 330096, P. R. of China
,
Wei Xiong
a   Department of Applied Chemistry, Jiang Xi Academic of Sciences, Nanchang 330096, P. R. of China
,
Hui-Bin Wang
a   Department of Applied Chemistry, Jiang Xi Academic of Sciences, Nanchang 330096, P. R. of China
,
Xiao-Na Dong
a   Department of Applied Chemistry, Jiang Xi Academic of Sciences, Nanchang 330096, P. R. of China
,
Jian-Wei Ji
b   Shaanxi Key Laboratory of Catalysis, School of Chemical & Environmental Science, Shaanxi, Sci-Tech University, Hanzhong, 723000 Shaanxi, P. R. of China   Email: kanxl433@nenu.edu.cn   Email: hjw19771985@163.com
,
Ju-Wu Hu  *
a   Department of Applied Chemistry, Jiang Xi Academic of Sciences, Nanchang 330096, P. R. of China
› Author AffiliationsFinancial support for this research by the National Natural Science Foundation of China (31260400, 21502109), Science Foundation for Young Doctors of Technology Department of Jiangxi Province (20161BBF60103), and start up Foundation of Shaanxi Key Laboratory of Catalysis (SLGQD13(2)-5, SLGKYQD2-12), and analysis and testing foundation of Jiang Xi Academic of Sciences are gratefully acknowledged.
Further Information

Publication History

Received: 23 March 2017

Accepted after revision: 14 June 2017

Publication Date:
25 July 2017 (online)

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Abstract

An efficient synthetic route to highly substituted pyrrolidone derivatives has been developed from an easily available alkynyl carboxamide and 4-methylbenzenesulfonic acid (PTSA). In the reaction, PTSA is not only used as acid catalyst but also as a reactant to provide a source for OTs group. A mechanism is proposed to involve the protonation of the alcohol substrate/cyclopropylcarbinol-homoallylic rearrangement/intramolecular N-nucleophilic cyclization reactions.

Keywords

pyrrolidones - alkynyl carboxamides - PTSA - intramolecular cyclization - ring opening

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588500. Included are experimental details, CIF data for 2n, and full characterization data, copies of 1H and 13C NMR spectra for compounds 2a–p, 3a,b and 4a.
  • Supporting Information
 

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