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脱羧点击环加成反应:一种合成取代1,2,3-三唑衍生物的新兴策略。

Decarboxylative click cycloaddition: an emerging strategy towards substituted 1,2,3-triazole derivatives.

作者信息

Kaur Manpreet, Bharti Divya, Kumar Vinod, Verma Praveen Kumar, Kumar Rakesh

机构信息

Laboratory of Organic Synthesis and Catalysis, Department of Chemistry, Central University of Punjab, Bathinda, 151401, India.

School of Advanced Chemical Sciences, Shoolini University, Solan, Himachal Pradesh, 173229, India.

出版信息

Mol Divers. 2025 Jun;29(3):2811-2827. doi: 10.1007/s11030-024-11014-4. Epub 2024 Nov 10.

Abstract

1,2,3-triazole is a vital structural motif of various drugs and therapeutic leads, as well as a linker for bioconjugation and molecular recognition. Cu-catalysed click cycloaddition of azides with terminal alkynes (CuAAc) is an important reaction to construct the triazole core. In recent years, various decarboxylative click strategies utilizing alkynoic acids as stable surrogates for low boiling or gaseous alkynes have been developed. For instance, propiolic acid, which is easy to transport, is a safe alternative for flammable gaseous acetylene. In this review article, we have covered the recent development in the decarboxylative click cycloaddition of alkynoic acids with azides leading to the synthesis of diversely substituted triazoles, including monosubstituted, 1,4-disubstituted and fully substituted 1,2,3-triazoles. Various aspects such as mechanistic insights and optimization conditions/role of catalyst are highlighted.

摘要

1,2,3-三唑是多种药物和治疗先导物的重要结构基序,也是生物共轭和分子识别的连接子。铜催化的叠氮化物与末端炔烃的环加成反应(CuAAc)是构建三唑核心的重要反应。近年来,已经开发了各种利用炔酸作为低沸点或气态炔烃的稳定替代物的脱羧点击策略。例如,易于运输的丙炔酸是易燃气态乙炔的安全替代品。在这篇综述文章中,我们涵盖了炔酸与叠氮化物的脱羧点击环加成反应的最新进展,该反应导致了各种取代的三唑的合成,包括单取代、1,4-二取代和全取代的1,2,3-三唑。文中突出了机理见解、优化条件/催化剂作用等各个方面。

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