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

页码：9259 / 9269

页数：11

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