Jaiswal Manoj K, Gupta Abhishek, Ansari Faisal J, Pandey Vinay K, Tiwari Vinod K
Department of Chemistry, Institute of Science, Banaras Hindu University, Varanasi, 221005, India.
Curr Org Synth. 2024;21(4):513-558. doi: 10.2174/1570179420666230418123350.
Immediately after the invention of 'Click Chemistry' in 2002, the regioselective 1,2,3- triazole scaffolds resulted from respective organic azides and terminal alkynes under Cu(I) catalysis have been well recognized as the functional heterocyclic core at the centre of modern organic chemistry, medicinal chemistry, and material sciences. This CuAAC reaction has several notable features including excellent regioselectivity, high-to-excellent yields, easy to execute, short reaction time, modular in nature, mild condition, readily available starting materials, etc. Moreover, the resulting regioselective triazoles can serve as amide bond isosteres, a privileged functional group in drug discovery and development. More than hundreds of reviews had been devoted to the 'Click Chemistry' in special reference to 1,4-disubstituted triazoles, while only little efforts were made for an opposite regioisomer i.e., 1,5-disubstituted triazole. Herein, we have presented various classical approaches for an expeditious synthesis of a wide range of biologically relevant 1,5- disubstituted 1,2,3-triazole analogues. The syntheses of such a class of diversly functionalized triazoles have emerged as a crucial investigation in the domain of chemistry and biology. This tutorial review covers the literature assessment on the development of various synthetic protocols for the functionalized 1,5-disubstituted triazoles reported during the last 12 years.
2002年“点击化学”发明后不久,在铜(I)催化下由相应的有机叠氮化物和末端炔烃生成的区域选择性1,2,3-三唑支架,已被公认为现代有机化学、药物化学和材料科学领域的功能性杂环核心。这种铜催化的叠氮化物-炔烃环加成反应(CuAAC)有几个显著特点,包括出色的区域选择性、高产率至优异产率、易于操作、反应时间短、本质上具有模块化、条件温和、起始原料容易获得等。此外,生成的区域选择性三唑可作为酰胺键等排体,这是药物发现和开发中的一个特殊官能团。已有数百篇综述专门论述了“点击化学”,特别是关于1,4-二取代三唑的,而对于相反的区域异构体即1,5-二取代三唑的研究却很少。在此,我们介绍了各种经典方法,用于快速合成一系列与生物相关的1,5-二取代1,2,3-三唑类似物。这类功能多样的三唑的合成已成为化学和生物学领域的一项关键研究。本专题综述涵盖了过去12年中报道的关于功能化1,5-二取代三唑各种合成方法发展的文献评估。