PREPARATION OF 2-SULFONYL-1,2,3-TRIAZOLES BY BASE-PROMOTED 1,2-REARRANGEMENT OF A SULFONYL GROUP

被引：26

作者：

Yamauchi, Motoshi ^{[1
]}

Miura, Tomoya ^{[1
]}

Murakami, Masahiro ^{[1
]}

机构：

[1] Kyoto Univ, Dept Synthet Chem & Biol Chem, Kyoto 6158510, Japan

来源：

HETEROCYCLES | 2010年 / 80卷 / 01期

关键词：

1,2,3-Triazole; Sulfonyl Group; Regioselective Reaction; Rearrangement; Base-Promoted Reaction; TERMINAL ALKYNES; 1,3-DIPOLAR CYCLOADDITIONS; EFFICIENT SYNTHESIS; AZIDES; 1,2,3-TRIAZOLES; ANTAGONISTS; CHEMISTRY; LIGATION;

D O I：

10.3987/COM-09-S(S)44

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1,2-Rearrangement of a sulfonyl group occurs on treatment of 1-sulfony1-1,2,3-triazoles with a catalytic amount of 4-dimethylaminopyridine (DMAP) in acetonitrile to give an equilibrium mixture of 1-sulfonyl- and 2-sulfonyl derivatives, with considerable predominance of the latter. Subsequent acidic treatment of the mixture caused selective hydrolysis of the 1-sulfonyl derivative, which led to the isolation of the 2-sulfony1-1,2,3-triazole in good total yield in a pure form.

引用

页码：177 / 181

页数：5

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