Das Jayanta, Dey Santu, Pathak Tanmaya
Department of Chemistry , Indian Institute of Technology Kharagpur , Kharagpur 721 302 , West Bengal , India.
J Org Chem. 2019 Dec 6;84(23):15437-15447. doi: 10.1021/acs.joc.9b02443. Epub 2019 Nov 19.
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.
已实现一种无金属的区域选择性合成羧基化1,4 - 二取代1,2,3 - 三唑（1,4 - cDTs）的方法。甲氧基羰基取代的乙烯基砜与有机叠氮化物反应，以一种操作简单的路线生成1,4 - cDTs。该反应与多种含有游离醇、酸、Boc保护的胺、酯、保护糖、长链烷烃、苄基、9 - 甲基蒽基和胆固醇基的有机叠氮化物进行，发现本质上具有通用性，可提供大量新的化学实体；二叠氮化物的反应大多生成所需产物以及一些意外产物。本文首次报道了使用适当官能化的乙烯基砜的环加成反应进行任何1,4 - 二取代1,2,3 - 三唑的无金属靶向合成。
