Synthesis 2017; 49(06): 1371-1379
DOI: 10.1055/s-0036-1588103
paper
© Georg Thieme Verlag Stuttgart · New York

Highly Efficient Synthesis of N-Sulfonylamidines via Silver-Catalyzed­ or Metal-Free Thermally Promoted Denitrogenative Amination of N-Sulfonyl-1,2,3-triazoles

Authors

  • Yue Feng

    a   Department of Chemistry, Northeast Normal University, 5268 Renmin Street, 130024 Changchun, P. R. of China   Email: lixq653@nenu.edu.cn
  • Wanjia Zhou

    a   Department of Chemistry, Northeast Normal University, 5268 Renmin Street, 130024 Changchun, P. R. of China   Email: lixq653@nenu.edu.cn
  • Ge Sun

    b   College of Pharmacy, Qiqihar Medical University, 333 Bukui Street, 161006 Qiqihar, P. R. of China
  • Peiqiu Liao

    a   Department of Chemistry, Northeast Normal University, 5268 Renmin Street, 130024 Changchun, P. R. of China   Email: lixq653@nenu.edu.cn
  • Xihe Bi*

    a   Department of Chemistry, Northeast Normal University, 5268 Renmin Street, 130024 Changchun, P. R. of China   Email: lixq653@nenu.edu.cn
    c   State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. of China
  • Xingqi Li*

    a   Department of Chemistry, Northeast Normal University, 5268 Renmin Street, 130024 Changchun, P. R. of China   Email: lixq653@nenu.edu.cn
Further Information

Publication History

Received: 21 September 2016

Accepted after revision: 27 October 2016

Publication Date:
28 November 2016 (online)


Graphical Abstract

Abstract

A highly efficient synthesis of N-sulfonylamidines from N-sulfonyl-1,2,3-triazoles and amines is reported. This transformation undergoes silver-catalyzed or metal-free thermally promoted denitrogenation of N-sulfonyl-1,2,3-triazoles to afford N-sulfonylketenimine intermediates and subsequent nucleophilic addition with amines. The amine plays dual roles as base and nucleophile.

Supporting Information