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Mendeleev Communications, 1992, Volume 2, Issue 3, Pages 85–86
DOI: https://doi.org/10.1070/MC1992v002n03ABEH000144
(Mi mendc5415)
 

This article is cited in 11 scientific papers (total in 11 papers)

1-Alkyl-1,2,4-triazinium Ylides as 1,3-Dipoles in a Cycloaddition Reaction with Diethyl Acetylenedicarboxylate

O. N. Chupakhina, B. V. Rudakovb, S. G. Alexeevb, S. V. Shorshnevc, V. N. Charushind

a I. Ya. Postovsky Institute of Organic Synthesis, Urals Branch of the Russian Academy of Sciences, Ekaterinburg, Russian Federation
b Urals State Technical University, Ekaterinburg, Russian Federation
c Ural Scientific Research Institute of Technology of Medical Preparations, Ekaterinburg, Russian Federation
d Department of Organic Chemistry, Urals State Technical University, Ekaterinburg, Russian Federation
Abstract: Deprotonation of 1-alkyl-5-phenyl-1,2,4-triazinium salts by triethylamine results in the formation of azomethyne ylides which undergo a 1,3-dipolar cycloaddition reaction with diethyl acetylenedicarboxylate to yield pyrrolo[2,1-f]1,2,4-triazines
Document Type: Article
Language: English


Citation: O. N. Chupakhin, B. V. Rudakov, S. G. Alexeev, S. V. Shorshnev, V. N. Charushin, “1-Alkyl-1,2,4-triazinium Ylides as 1,3-Dipoles in a Cycloaddition Reaction with Diethyl Acetylenedicarboxylate”, Mendeleev Commun., 2:3 (1992), 85–86
Linking options:
  • https://www.mathnet.ru/eng/mendc5415
  • https://www.mathnet.ru/eng/mendc/v2/i3/p85
  • This publication is cited in the following 11 articles:
    1. Veronika Šlachtová, Simona Bellová, Agustina La‐Venia, Juraj Galeta, Martin Dračínský, Karel Chalupský, Alexandra Dvořáková, Helena Mertlíková‐Kaiserová, Peter Rukovanský, Rastislav Dzijak, Milan Vrabel, “Triazinium Ligation: Bioorthogonal Reaction of N1‐Alkyl 1,2,4‐Triazinium Salts**”, Angewandte Chemie, 135:36 (2023)  crossref
    2. Veronika Šlachtová, Simona Bellová, Agustina La‐Venia, Juraj Galeta, Martin Dračínský, Karel Chalupský, Alexandra Dvořáková, Helena Mertlíková‐Kaiserová, Peter Rukovanský, Rastislav Dzijak, Milan Vrabel, “Triazinium Ligation: Bioorthogonal Reaction of N1‐Alkyl 1,2,4‐Triazinium Salts**”, Angew Chem Int Ed, 62:36 (2023)  crossref
    3. Nataliya N. Mochulskaya, Svetlana K. Kotovskaya, Ilya I. Butorin, Mikhail V. Varaksin, Valery N. Charushin, Vladimir L. Rusinov, Yana L. Esaulkova, Alexander V. Slita, Polina A. Ilyina, Vladimir V. Zarubaev, “Bioactive Pyrrolo[2,1-f][1,2,4]triazines: Synthesis, Molecular Docking, In Vitro Cytotoxicity Assay and Antiviral Studies”, Chemistry, 5:4 (2023), 2657  crossref
    4. Juraj Galeta, Veronika Šlachtová, Martin Dračínský, Milan Vrabel, “Regio- and Diastereoselective 1,3-Dipolar Cycloadditions of 1,2,4-Triazin-1-ium Ylides: a Straightforward Synthetic Route to Polysubstituted Pyrrolo[2,1-f][1,2,4]triazines”, ACS Omega, 7:24 (2022), 21233  crossref
    5. Gregory R. Ott, David A. Favor, “Pyrrolo[2,1-f][1,2,4]triazines: From C-nucleosides to kinases and back again, the remarkable journey of a versatile nitrogen heterocycle”, Bioorganic & Medicinal Chemistry Letters, 27:18 (2017), 4238  crossref
    6. Tho Thieu, Joseph A. Sclafani, Daniel V. Levy, Andrew McLean, Henry J. Breslin, Gregory R. Ott, Roger P. Bakale, Bruce D. Dorsey, “Discovery and Process Synthesis of Novel 2,7-Pyrrolo[2,1-f][1,2,4]triazines”, Org. Lett., 13:16 (2011), 4204  crossref
    7. N. N. Mochulskaya, A. A. Andreiko, V. N. Charushin, B. V. Shulgin, D. V. Raikov, V. I. Solomonov, “Intermolecular and intramolecular cycloaddition reactions of 1-ethyl-1,2,4-triazinium salts with alkynes”, Mendeleev Commun., 11:1 (2001), 19–21  mathnet  crossref
    8. Comprehensive Heterocyclic Chemistry II, 1996, 1169  crossref
    9. Drago R. Sliskovic, Comprehensive Heterocyclic Chemistry II, 1996, 389  crossref
    10. O. N. CHUPAKHIN, B. V. RUDAKOV, S. G. ALEXEEV, S. V. SHORSHNEV, V. N. CHARUSHIN, “ChemInform Abstract: 1‐Alkyl‐1,2,4‐triazinium Ylides as 1,3‐Dipoles in a Cycloaddition Reaction with Diethyl Acetylenedicarboxylate.”, ChemInform, 24:15 (1993)  crossref
    11. DEREK T. Hurst, Progress in Heterocyclic Chemistry, 5, A Critical Review of the 1992 Literature Preceded by two Chapters on Current Heterocyclic Topics, 1993, 239  crossref
    Citing articles in Google Scholar: Russian citations, English citations
    Related articles in Google Scholar: Russian articles, English articles
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