期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 84, 期 23, 页码 15437-15447出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b02443
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资金
- Department of Science and Technology (DST), New Delhi [SB/S1/OC-30/2014]
- Indian Institute of Technology, Kharagpur
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.
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