Metal-Free Synthetic Approach to 3-Monosubstituted Unsymmetrical 1,2,4,5-Tetrazines Useful for Bioorthogonal Reactions

被引：64

作者：

Qu, Yangyang ^{[1
]}

Sauvage, Francois-Xavier ^{[1
]}

Clavier, Gilles ^{[1
]}

Miomandre, Fabien ^{[1
]}

Audebert, Pierre ^{[1
]}

机构：

[1] PPSM CNRS ENS Paris Saclay, 61 Ave President Wilson, F-94235 Cachan, France

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2018年 / 57卷 / 37期

基金：

欧盟地平线“2020”;

关键词：

bioorthogonal reactions; click chemistry; cycloadditions; metal-free synthesis; tetrazines; GENETIC-CODE EXPANSION; LIVE-CELL; LIVING CELLS; S-TETRAZINE; FLUORESCENCE; HYDRAZINE; CHEMISTRY; PROBES; MICROSCOPY; MOLECULES;

D O I：

10.1002/anie.201804878

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A facile, efficient and metal-free synthetic approach to 3-monosubstituted unsymmetrical 1,2,4,5-tetrazines is presented. Dichloromethane (DCM) is for the first time recognized as a novel reagent in the synthetic chemistry of tetrazines. Using this novel approach 11 3-aryl/alkyl 1,2,4,5-tetrazines were prepared in excellent yields (up to 75%). The mechanism of this new reaction, including the role of DCM in the tetrazine ring formation, has been investigated by (13)Clabeling of DCM, and is also presented and discussed as well as the photophysical and electrochemical properties.

引用

页码：12057 / 12061

页数：5

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