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
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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
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
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
Comprehensive Heterocyclic Chemistry II, 1996, 1169
Drago R. Sliskovic, Comprehensive Heterocyclic Chemistry II, 1996, 389
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)
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