1,3-dipolar cycloaddition of azides with electron-deficient alkynes under mild condition in water

被引：151

作者：

Li, ZM

Seo, TS

Ju, JY

机构：

[1] Columbia Univ Coll Phys & Surg, Columbia Genome Ctr, New York, NY 10032 USA

[2] Columbia Univ, Dept Chem Engn, New York, NY 10027 USA

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 15期

基金：

美国国家卫生研究院; 美国国家科学基金会;

关键词：

1,3-dipolar cycloaddition; electron-deficient alkynes; 5 '-azido DNA;

D O I：

10.1016/j.tetlet.2004.02.089

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report a simple synthetic protocol for the 1,3-dipolar cycloaddition of azides with electron-deficient alkynes. Alkyne with at least one neighboring electron-withdrawing group proceeds with the cycloaddition successfully without any catalysts at room temperature in water. Under this simple condition, we evaluated a series of small molecule model reactions and then coupled an azido-DNA molecule with electron-deficient alkynes for the formation of [1,2,3]-triazole heterocycle, providing a potential method for introducing functional groups to DNA under biological conditions. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：3143 / 3146

页数：4

共 26 条

[21]

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[22] Click chemistry to construct fluorescent oligonucleotides for DNA sequencing [J].