Metal-Free Route to Carboxylated 1,4-Disubstituted 1,2,3-Triazoles from Methoxycarbonyl-Modified Vinyl Sulfone

被引：15

作者：

Das, Jayanta ^{[1
]}

Dey, Santu ^{[1
]}

Pathak, Tanmaya ^{[1
]}

机构：

[1] Indian Inst Technol Kharagpur, Dept Chem, Kharagpur 721302, W Bengal, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 23期

关键词：

1,3-DIPOLAR CYCLOADDITION; CLICK CHEMISTRY; AZIDE; DERIVATIVES;

D O I：

10.1021/acs.joc.9b02443

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A metal-free alternative to the regioselective synthesis of carboxylated 1,4-disubstituted 1,2,3-triazoles (1,4-cDTs) has been accomplished, A methoxycarbonyl-substituted vinyl sulfone on reactions with organic azides resulted in the formation of 1,4-cDTs in an operationally simple route. The reaction, carried out with a variety of organic azides containing free alcohol, acid, Boc-protected amine, ester, protected sugars, long-chain alkanes, benzyl, 9-methylanthracenyl, and cholesteryl groups, was found to be general in nature, which afforded a plethora of new chemical entities; reactions of diazides generated mostly the desired and a few unexpected products. This article reports for the first time the targeted metal-free synthesis of any 1,4-disubstituted 1,2,3-triazole using the cycloaddition reactions of an appropriately functionalized vinyl sulfone.

引用

收藏

页码：15437 / 15447

页数：11

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