Chemoselective preparation of disymmetric bistriazoles from bisalkynes

被引：30

作者：

Elamari, Hichem ^{[1
,2
]}

Meganem, Faouzi ^{[2
]}

Herscovici, Jean ^{[1
]}

Girard, Christian ^{[1
]}

机构：

[1] Ecole Natl Super Chim Paris, Unite Pharmacol Chim Genet & Imagerie, UMR8151, Chim ParisTech,CNRS,INSERM,U1022, F-75005 Paris, France

[2] Fac Sci Bizerte, Lab Chim Organ & Applicat, Jarzouna 7021, Bizerte, Tunisia

来源：

TETRAHEDRON LETTERS | 2011年 / 52卷 / 06期

关键词：

Huisgen's reaction; Click chemistry; Activation; Alkyne; Azide; AZIDE-ALKYNE CYCLOADDITION; CLICK CHEMISTRY; HUISGEN CYCLOADDITION; SOLID-PHASE; REACTIVITY;

D O I：

10.1016/j.tetlet.2010.11.141

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Best of both worlds, molecules bearing two alkyne groups, activated and unactivated, can selectively react on the activated one in a copper-free version of Huisgen's reaction to form a first triazole ring, with a good selectivity toward the 1,4-isomer, which is solely isolated by a simple trituration procedure. The other alkyne function is then submitted to the selective reaction using a polymer-supported copper(I) catalyst to form a second triazole ring. This gave access to disymmetric bistriazoles without the need of protection using simple, easy, and fast procedures. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：658 / 660

页数：3

共 33 条

[1] A strain-promoted [3+2] azide-alkyne cycloaddition for covalent modification of blomolecules in living systems [J].