Triazines, tetrazines, and fused ring polyaza systems

Hiebel, Marie‐Aude; Suzenet, Franck

doi:10.1016/b978-0-323-98410-2.00014-x

Cited by 4 publications

(1 citation statement)

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“…This review aims to summarize and analyze the synthesis, IEDDA reactions, and applications of various uncondensed aromatic triazines, while the fused triazines, dihydrotriazines, and triazineones are generally not within this scope. 58 2. 1,2,4-TRIAZINES 1,2,4-Triazines, also known as a-triazines, are an asymmetric type of triazines.…”

Section: Introductionmentioning

confidence: 99%

Triazines: Syntheses and Inverse Electron-demand Diels–Alder Reactions

et al. 2021

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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.

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Section: Introductionmentioning

confidence: 99%