A Metal-Free Three-Component Reaction for the Regioselective Synthesis of 1,4,5-Trisubstituted 1,2,3-Triazoles

被引：160
|
作者：
Thomas, Joice [1 ]
John, Jubi [1 ]
Parekh, Nikita [1 ]
Dehaen, Wim [1 ]
机构：
[1] Katholieke Univ Leuven, Dept Chem, B-3001 Leuven, Belgium
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 38期
关键词：
dipolar cycloaddition; multicomponent reactions; organocatalysis; regioselectivity; triazole; RUTHENIUM-CATALYZED CYCLOADDITION; CLICK CHEMISTRY; REGIOSPECIFIC SYNTHESIS; AZIDOPHENYL ARYLSELENIDES; ORGANOCATALYTIC SYNTHESIS; TERMINAL ALKYNES; AZIDE-ALKYNE; DISCOVERY; ALDEHYDES; CASCADE;
D O I：
10.1002/anie.201403453
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A metal-free three-component reaction to synthesize 1,4,5-trisubstituted 1,2,3-triazoles from readily available building blocks, such as aldehydes, nitroalkanes, and organic azides, is described. The process is enabled by an organocatalyzed Knoevenagel condensation of the formyl group with the nitro compound, which is followed by the 1,3-dipolar cycloaddition of the azide to the activated alkene. The reaction features an excellent substrate scope, and the products are obtained with high yield and regioselectivity. This method can be utilized for the synthesis of fused triazole heterocycles and materials with several triazole moieties.
引用
收藏
页码：10155 / 10159
页数：5
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