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

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
› Author Affiliations
Further Information

Publication History

Received: 21 September 2016

Accepted after revision: 27 October 2016

Publication Date:
28 November 2016 (online)


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

 
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