Synthesis 2013; 45(1): 45-52
DOI: 10.1055/s-0032-1316821
paper
© Georg Thieme Verlag Stuttgart · New York

An Efficient Synthesis of 2-Aminothiophenes via the Gewald Reaction Catalyzed by an N-Methylpiperazine-Functionalized Polyacrylonitrile Fiber

Authors

  • Lichao Ma

    Department of Chemistry, School of Sciences, Tianjin University, No.92 Weijin Road, Tianjin 300072, P. R. of China   Fax: +86(22)27403475   Email: zhangwenqin@tju.edu.cn
  • Liwei Yuan

    Department of Chemistry, School of Sciences, Tianjin University, No.92 Weijin Road, Tianjin 300072, P. R. of China   Fax: +86(22)27403475   Email: zhangwenqin@tju.edu.cn
  • Changzhu Xu

    Department of Chemistry, School of Sciences, Tianjin University, No.92 Weijin Road, Tianjin 300072, P. R. of China   Fax: +86(22)27403475   Email: zhangwenqin@tju.edu.cn
  • Guowei Li

    Department of Chemistry, School of Sciences, Tianjin University, No.92 Weijin Road, Tianjin 300072, P. R. of China   Fax: +86(22)27403475   Email: zhangwenqin@tju.edu.cn
  • Minli Tao

    Department of Chemistry, School of Sciences, Tianjin University, No.92 Weijin Road, Tianjin 300072, P. R. of China   Fax: +86(22)27403475   Email: zhangwenqin@tju.edu.cn
  • Wenqin Zhang*

    Department of Chemistry, School of Sciences, Tianjin University, No.92 Weijin Road, Tianjin 300072, P. R. of China   Fax: +86(22)27403475   Email: zhangwenqin@tju.edu.cn
Further Information

Publication History

Received: 12 September 2012

Accepted after revision: 09 November 2012

Publication Date:
29 November 2012 (online)


Graphical Abstract

Abstract

A new N-methylpiperazine-functionalized polyacrylonitrile fiber has been developed to catalyze the Gewald reaction between 2,5-dihydroxy-1,4-dithiane and activated nitriles to afford 3-substituted 2-aminothiophenes in good to excellent yields (65–91%). Low catalyst loading (8.0 mol%), simple procedure, high yields, excellent recyclability, and reusability (up to 10 times with minimal loss of catalytic activity) are attractive features of this fiber catalyst.

Supporting Information