Metal-free, highly regioselective sulfonylation of NH-1,2,3-triazoles with sodium sulfinates and thiosulfonates

被引：24
|
作者：
Reddy, Raju Jannapu [1 ]
Shankar, Angothu [1 ]
Waheed, Md [1 ]
Nanubolu, Jagadeesh Babu [2 ]
机构：
[1] Osmania Univ, Dept Chem, Hyderabad 500007, Andhra Prades, India
[2] Indian Inst Chem Technol, CSIR, Ctr Xray Crystallog, Hyderabad 500007, Andhra Prades, India
来源：
TETRAHEDRON LETTERS | 2018年 / 59卷 / 21期
关键词：
Iodine; Sodium sulfinates; Sulfonylation; Thiosulfonates; Triazoles; AZIDE-ALKYNE CYCLOADDITION; NONACTIVATED TERMINAL ALKYNES; 3-COMPONENT COUPLING REACTION; 1,5-DISUBSTITUTED 1,2,3-TRIAZOLES; EFFICIENT SYNTHESIS; TRANSITION-METAL; SUBSTITUTED 1,2,3-TRIAZOLES; CLICK CHEMISTRY; TRIAZOLES; CONSTRUCTION;
D O I：
10.1016/j.tetlet.2018.04.023
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A convenient and metal-free protocol for the highly regioselective sulfonylation of NH-1,2,3-triazoles is described. A range of readily accessible NH-1,2,3-triazoles were sulfonylated with various aryl sulfinates in the presence of molecular iodine. The scope was extended to thiosulfonates as an efficient sulfonylating agent and nitrochromene derived triazoles were also explored for selective N-sulfonylation. A variety of synthetically viable N-2-sulfonyl triazoles were obtained in moderate to high yields with excellent regioselectivities via N-S bond construction under mild reaction conditions. (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2014 / 2017
页数：4
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