ArticleThe Journal of organic chemistry2022
1,2,3,5-Tetrazines: A General Synthesis, Cycloaddition Scope, and Fundamental Reactivity Patterns.
Article in The Journal of organic chemistry, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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Who cites it
4 citing papers in PubMed.
- A bibliometric review of triazine hybrids: synthesis, reactions, and applications spanning the last quarter-century (2000-2025).RSC advances · 2025Review
- Second-Generation Catalyst System for Ag-Mediated Liebeskind-Srogl Coupling of Tetrazine Thioethers with Arylboronic Acids.The Journal of organic chemistry · 2025Article
- Supernatural Products.The Chemist · 2025Article
- Efficient Approaches to the Design of Six-Membered Polyazacyclic Compounds-Part 1: Aromatic Frameworks.Molecules (Basel, Switzerland) · 2025Review
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Authors and funding
2 authors.
Funding
Abstract
Despite the explosion of interest in heterocyclic azadienes, 1,2,3,5-tetrazines remain unexplored. Herein, the first general synthesis of this new class of heterocycles is disclosed. Its use in the preparation of a series of derivatives, and the first study of substituent effects on their cycloaddition reactivity, mode, and regioselectivity provide the foundation for future use. Their reactions with amidine, electron-rich, and strained dienophiles reveal unique fundamental reactivity patterns (4,6-dialkyl-1,2,3,5-tetrazines > 4,6-diaryl-1,2,3,5-tetrazines for amidines but slower with strained dienophiles), an exclusive C4/N1 mode of cycloaddition, and dominant alkyl versus aryl control on regioselectivity. An orthogonal reactivity of 1,2,3,5-tetrazines and the well-known isomeric 1,2,4,5-tetrazines is characterized, and detailed kinetic and mechanistic investigations of the remarkably fast reaction of 1,2,3,5-tetrazines with amidines, especially 4,6-dialkyl-1,2,3,5-tetrazines, established the mechanistic origins underlying the reactivity patterns and key features needed for future applications.
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