ArticleJournal of the American Chemical Society2019
Synthesis, Characterization, and Cycloaddition Reactivity of a Monocyclic Aromatic 1,2,3,5-Tetrazine.
Article in Journal of the American Chemical Society, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed.
- Computational Study of Ignored Pericyclic Reactions: Rearrangements of 1,2-Bis(Diazo)Alkanes to 1,2,3,4-Tetrazines and Subsequent Fragmentations.Angewandte Chemie (International ed. in English) · 2025Article
- Efficient Approaches to the Design of Six-Membered Polyazacyclic Compounds-Part 1: Aromatic Frameworks.Molecules (Basel, Switzerland) · 2025Review
- Recent advances in metal-free catalysts for the synthesis of N-heterocyclic frameworks focusing on 5- and 6-membered rings: a review.RSC advances · 2025Review
- Synthesis of CThe Journal of organic chemistry · 2024Article
- Site-specific dual encoding and labeling of proteins via genetic code expansion.Cell chemical biology · 2023Review
- 1,2,3,5-Tetrazines: A General Synthesis, Cycloaddition Scope, and Fundamental Reactivity Patterns.The Journal of organic chemistry · 2022Article
- Functionalized Triazines and Tetrazines: Synthesis and Applications.Topics in current chemistry (Cham) · 2022Review
- Mechanistic Insights into the Reaction of Amidines with 1,2,3-Triazines and 1,2,3,5-Tetrazines.Journal of the American Chemical Society · 2022Article
- N1/N4 1,4-Cycloaddition of 1,2,4,5-Tetrazines with Enamines Promoted by the Lewis Acid ZnClThe Journal of organic chemistry · 2022Article
- Reaction Scope of Methyl 1,2,3-Triazine-5-carboxylate with Amidines and the Impact of C4/C6 Substitution.The Journal of organic chemistry · 2021Article
- Selective N1/N4 1,4-Cycloaddition of 1,2,4,5-Tetrazines Enabled by Solvent Hydrogen Bonding.Journal of the American Chemical Society · 2020Article
- Metabolism of a Bioorthogonal PET Tracer Candidate [Molecular pharmaceutics · 2020Article
- Bioorthogonal Ligations and Cleavages in Chemical Biology.ChemistryOpen · 2020Review
- Calculation of magnetic response properties of tetrazines.RSC advances · 2020Article
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Authors and funding
2 authors.
Funding
Abstract
Herein we disclose the synthesis and full characterization of the first monocyclic aromatic 1,2,3,5-tetrazine, 4,6-diphenyl-1,2,3,5-tetrazine. Initial studies of its cycloaddition reactivity, mode, regioselectivity, and scope illustrate that it participates as the 4π-component of well-behaved inverse electron demand Diels-Alder reactions where it preferentially reacts with electron-rich or strained dienophiles. It was found to exhibit an intrinsic reactivity comparable to that of the isomeric 3,6-diphenyl-1,2,4,5-tetrazine, display a single mode of cycloaddition with reaction only across C4/N1 (no N2/N5 cycloaddition observed), proceed with a predictable regioselectivity (dienophile most electron-rich atom attaches to C4), and manifest additional reactivity complementary to the isomeric 1,2,4,5-tetrazines. It not only exhibits a remarkable cycloaddition reactivity, surprisingly good stability (e.g., stable to chromatography, long-term storage, presence of H
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