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三唑在有机合成中的新进展:探索其作为胶凝剂的潜力

Emerging Aspects of Triazole in Organic Synthesis: Exploring its Potential as a Gelator.

作者信息

Vasanthan Rabecca Jenifer, Pradhan Sheersha, Thangamuthu Mohan Das

机构信息

Department of Chemistry, School of Basic and Applied Sciences, Central University of Tamil Nadu (CUTN), Thiruvarur, 610 005, India.

出版信息

Curr Org Synth. 2024;21(4):456-512. doi: 10.2174/1570179420666221010094531.

Abstract

Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuAAC) - commonly known as the "click reaction" - serves as the most effective and highly reliable tool for facile construction of simple to complex designs at the molecular level. It relates to the formation of carbon heteroatomic systems by joining or clicking small molecular pieces together with the help of various organic reactions such as cycloaddition, conjugate addition, ring-opening, etc. Such dynamic strategy results in the generation of triazole and its derivatives from azides and alkynes with three nitrogen atoms in the five-membered aromatic azole ring that often forms gel-assembled structures having gelating properties. These scaffolds have led to prominent applications in designing advanced soft materials, 3D printing, ion sensing, drug delivery, photonics, separation, and purification. In this review, we mainly emphasize the different mechanistic aspects of triazole formation, which includes the synthesis of sugar-based and non-sugar-based triazoles, and their gel applications reported in the literature for the past ten years, as well as the upcoming scope in different branches of applied sciences.

摘要

铜(I)催化的叠氮化物-炔烃1,3-偶极环加成反应(CuAAC)——通常被称为“点击反应”——是在分子水平上轻松构建从简单到复杂结构的最有效且高度可靠的工具。它涉及通过各种有机反应,如环加成、共轭加成、开环等,将小分子片段连接或“点击”在一起,形成碳杂原子体系。这种动态策略通过叠氮化物和炔烃生成三唑及其衍生物,五元芳香唑环中有三个氮原子,这些结构通常会形成具有凝胶化特性的凝胶组装结构。这些支架在设计先进的软材料、3D打印、离子传感、药物递送、光子学、分离和纯化等方面有显著应用。在本综述中,我们主要强调三唑形成的不同机理方面,包括糖基和非糖基三唑的合成,以及过去十年文献中报道的它们的凝胶应用,还有应用科学不同分支中的未来发展前景。

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