ArticleOrganic letters2015
Cycloadditions of 1,2,3-Triazines Bearing C5-Electron Donating Substituents: Robust Pyrimidine Synthesis.
Article in Organic letters, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed.
- Molecular Editing of 5-Alkynyl-1,2,3-triazines via a Silver-Mediated Skeletal Remodeling Approach: Solvent-Controlled Switchable Synthesis of Functionalized Pyrroles and Furans.The Journal of organic chemistry · 2025Article
- Cysteine-Specific Multifaceted Bioconjugation of Peptides and Proteins Using 5-Substituted 1,2,3-Triazines.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Unified Access to Pyrimidines and Quinazolines Enabled by N-N Cleaving Carbon Atom Insertion.Journal of the American Chemical Society · 2022Article
- Article
- 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
- 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
- Inverse Electron Demand Diels-Alder Reactions of Heterocyclic Azadienes, 1-Aza-1,3-Butadienes, Cyclopropenone Ketals, and Related Systems. A Retrospective.The Journal of organic chemistry · 2019Review
- Synthesis, Characterization, and Rapid Cycloadditions of 5-Nitro-1,2,3-triazine.Organic letters · 2018Article
- Computational Exploration of Concerted and Zwitterionic Mechanisms of Diels-Alder Reactions between 1,2,3-Triazines and Enamines and Acceleration by Hydrogen-Bonding Solvents.Journal of the American Chemical Society · 2017Article
- Direct Synthesis of β-Aminoenals through Reaction of 1,2,3-Triazine with Secondary Amines.Organic letters · 2017Article
- Catalysis of Heterocyclic Azadiene Cycloaddition Reactions by Solvent Hydrogen Bonding: Concise Total Synthesis of Methoxatin.Journal of the American Chemical Society · 2016Article
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2 authors.
Funding
Abstract
The examination of the cycloaddition reactions of 1,2,3-triazines 17-19, bearing electron-donating substituents at C5, are described. Despite the noncomplementary 1,2,3-triazine C5 substituents, amidines were found to undergo a powerful cycloaddition to provide 2,5-disubstituted pyrimidines in excellent yields (42-99%; EDG = SMe > OMe > NHAc). Even select ynamines and enamines were capable of cycloadditions with 17, but not 18 or 19, to provide trisubstituted pyridines in modest yields (37-40% and 33% respectively).
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