Synthesis of Thiazole-2(3H)-ones via [3,3]-Sigmatropic Rearrangement/5-exo-dig Cyclization of N-Propargylamines

被引：11
作者：
Behera, Bipin Kumar [1 ]
Shit, Sudip [1 ]
Biswas, Subhamoy [1 ]
Saikia, Anil K. [1 ]
机构：
[1] Indian Inst Technol Guwahati, Dept Chem, Gauhati 781039, India
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 87卷 / 14期
关键词：
EFFICIENT SYNTHESIS; DERIVATIVES; TRIFLUOROMETHANETHIOLATE; CYTOTOXICITY; ALKYNES; AGSCF3; SULFUR; ACCESS; AMINES; MILD;
D O I：
10.1021/acs.joc.2c00991
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
ABSTRACT: An efficient methodology has been developed for the synthesis of both di- and trisubstituted thiazol-2(3H)-ones from Npropargylamines and silver(I) trifluoromethanethiolate (AgSCF3) in good yields. The reaction proceeds via [3,3]-sigmatropic rearrangement/5-exodig cyclization of N-propargylamines. The starting material can be easily prepared from the A3-coupling reaction of amines, aldehydes, and alkynes. The methodology can be extended for the synthesis of thiozole-2(3H)thione derivatives, and photophysical properties have been studied for some synthesized compounds.
引用
收藏
页码：9259 / 9269
页数：11
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