Abstract:
Azomethyne ylides generated from 3-alkylthio substituted 1-alkyl-5-aryl-1,2,4-triazinium salts 4a–c on treatment with triethylamine undergo 1,3-dipolar cycloaddition with dimethyl acetylenedicarboxylate to give pyrrolo[2,1-f] [1,2,4]triazines, while 1-ethyl-5- phenyl-1,2,4-triazinium salts 1a,b bearing the C≡C bond in the side-chain 3-alkynylthio substituent react with acetylenes to undergo either intermolecular 1,3-dipolar cycloaddition or intramolecular inverse electron demand Diels–Alder reactions.
Document Type:
Article
Language: English
Citation:
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
Linking options:
https://www.mathnet.ru/eng/mendc4196
https://www.mathnet.ru/eng/mendc/v11/i1/p19
This publication is cited in the following 7 articles:
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)
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)
Anna V. Gulevskaya, Julia I. Nelina-Nemtseva, “1,3-Dipolar cycloaddition reactions of azomethine ylides and alkynes”, Chem Heterocycl Comp, 54:12 (2018), 1084
A. M. Prokhorov, D. N. Kozhevnikov, “Reactions of triazines and tetrazines with dienophiles (Review)”, Chem Heterocycl Comp, 48:8 (2012), 1153
V. Charushin, V. Rusinov, O. Chupakhin, Comprehensive Heterocyclic Chemistry III, 2008, 95
L. I. Tarkhov, V. A. Potemkin, D. N. Kozhevnikov, “Experimental Investigation and Modeling of the Cathodoluminescence of 1,2,4-Triazine Derivatives”, J Appl Spectrosc, 72:5 (2005), 636
Nataliya N. Mochulskaya, Anatoly A. Andreiko, Valery N. Charushin, Boris V. Shulgin, Dmitry V. Raikov, Vladimir I. Solomonov, “ChemInform Abstract: Intermolecular and Intramolecular Cycloaddition Reactions of 1‐Ethyl‐1,2,4‐triazinium Salts with Alkynes.”, ChemInform, 32:28 (2001)
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