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Triazines: Syntheses and Inverse Electron-demand Diels–Alder Reactions
Chemical Reviews ( IF 62.1 ) Pub Date : 2021-09-29 , DOI: 10.1021/acs.chemrev.1c00611
Fa-Guang Zhang 1, 2 , Zhen Chen 3 , Xiaodong Tang 1, 2 , Jun-An Ma 1, 2
Affiliation  

Triazines are an important class of six-membered aromatic heterocycles possessing three nitrogen atoms, resulting in three types of regio-isomers: 1,2,4-triazines (a-triazines), 1,2,3-triazines (v-triazines), and 1,3,5-triazines (s-triazines). Notably, the application of triazines as cyclic aza-dienes in inverse electron-demand Diels–Alder (IEDDA) cycloaddition reactions has been established as a unique and powerful method in N-heterocycle synthesis, natural product preparation, and bioorthogonal chemistry. In this review, we comprehensively summarize the advances in the construction of these triazines via annulation and ring-expansion reactions, especially emphasizing recent developments and challenges. The synthetic transformations of triazines are focused on IEDDA cycloaddition reactions, which have allowed access to a wide scope of heterocycles, including pyridines, carbolines, azepines, pyridazines, pyrazines, and pyrimidines. The utilization of triazine IEDDA reactions as key steps in natural product synthesis is also discussed. More importantly, a particular attention is paid on the bioorthogonal application of triazines in fast click ligation with various strained alkenes and alkynes, which opens a new opportunity for studying biomolecules in chemical biology.

中文翻译:

三嗪:合成和逆电子需求 Diels-Alder 反应

三嗪是一类重要的六元芳香杂环,具有三个氮原子,产生三种区域异构体:1,2,4-三嗪(a-三嗪),1,2,3-三嗪(v-三嗪) , 和 1,3,5-三嗪 ( s-三嗪)。值得注意的是,三嗪作为环状氮杂二烯在逆电子需求 Diels-Alder (IEDDA) 环加成反应中的应用已被确立为N-杂环合成、天然产物制备和生物正交化学。在这篇综述中,我们全面总结了通过废除和扩环反应构建这些三嗪的进展,特别强调了最近的发展和挑战。三嗪的合成转化主要集中在 IEDDA 环加成反应上,该反应允许获得广泛的杂环,包括吡啶、咔啉、氮杂环庚烷、哒嗪、吡嗪和嘧啶。还讨论了利用三嗪 IEDDA 反应作为天然产物合成的关键步骤。更重要的是,特别关注三嗪在与各种烯烃和炔烃的快速点击连接中的生物正交应用,这为化学生物学中的生物分子研究开辟了新的机遇。
更新日期:2021-12-08
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