功能化 1,5-二取代三唑合成的最新进展。

IF 1.7 4区 化学 Q3 CHEMISTRY, ORGANIC Current organic synthesis Pub Date : 2024-01-01 DOI:10.2174/1570179420666230418123350
Manoj K Jaiswal, Abhishek Gupta, Faisal J Ansari, Vinay K Pandey, Vinod K Tiwari
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引用次数: 0

摘要

2002 年发明 "点击化学"(Click Chemistry)后,在 Cu(I)催化下由各自的有机叠氮化物和端炔类化合物生成的具有区域选择性的 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中心的功能性杂环核心。这种 CuAAC 反应具有几个显著特点,包括极佳的区域选择性、高至极佳的产率、易于执行、反应时间短、模块化、条件温和、起始材料易得等。此外,生成的具有区域选择性的三唑可以作为酰胺键异构体,是药物发现和开发中的一个重要官能团。关于 "点击化学",特别是关于 1,4-二取代三唑的研究已经发表了数百篇综述,而关于 1,5-二取代三唑的研究却很少。在此,我们介绍了快速合成多种生物相关的 1,5-二取代 1,2,3- 三唑类似物的各种经典方法。合成这类具有多种功能的三唑已成为化学和生物学领域的一项重要研究。本教程综述了过去 12 年中有关功能化 1,5-二取代三唑的各种合成方案的文献评估。
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Recent Progress on Synthesis of Functionalized 1,5-Disubstituted Triazoles.

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.

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来源期刊
Current organic synthesis
Current organic synthesis 化学-有机化学
CiteScore
3.40
自引率
5.60%
发文量
86
审稿时长
6-12 weeks
期刊介绍: Current Organic Synthesis publishes in-depth reviews, original research articles and letter/short communications on all areas of synthetic organic chemistry i.e. asymmetric synthesis, organometallic chemistry, novel synthetic approaches to complex organic molecules, carbohydrates, polymers, protein chemistry, DNA chemistry, supramolecular chemistry, molecular recognition and new synthetic methods in organic chemistry. The frontier reviews provide the current state of knowledge in these fields and are written by experts who are internationally known for their eminent research contributions. The journal is essential reading to all synthetic organic chemists. Current Organic Synthesis should prove to be of great interest to synthetic chemists in academia and industry who wish to keep abreast with recent developments in key fields of organic synthesis.
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