Abstract:
Nucleophilic substitution of hydrogen by cyano and alkoxy groups in 1,2,4-triazine-4-oxides is reported.
Document Type:
Article
Language: English
Citation:
O. N. Chupakhin, V. L. Rusinov, E. N. Ulomsky, D. N. Kozhevnikov, H. Neunhoeffer, “Nucleophilic substitution of hydrogen in the reaction of 1,2,4-triazine-4-oxides with cyanides”, Mendeleev Commun., 7:2 (1997), 66–67
Linking options:
https://www.mathnet.ru/eng/mendc4785
https://www.mathnet.ru/eng/mendc/v7/i2/p66
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A. P. Krinochkin, M. R. Guda, D. S. Kopchuk, N. V. Slovesnova, I. S. Kovalev, M. I. Savchuk, Ya. K. Shtaitz, E. S. Starnovskaya, G. V. Zyryanov, O. N. Chupakhin, “Efficient Synthesis of 5-[3(4)-(5-Phenyl-1,3,4-oxadiazol-2-yl)anilino]-1,2,4-triazines”, Russ J Org Chem, 57:10 (2021), 1753
E. S. Starnovskaya, M. I. Savchuk, Ya. K. Shtaitz, D. S. Kopchuk, I. S. Kovalev, D. E. Pavlyuk, A. F. Khasanov, G. V. Zyryanov, O. N. Chupakhin, “Polynuclear Aromatic Amines as N-Nucleophiles in the ipso-Substitution of the Cyano Group in 1,2,4-Triazines”, Russ J Org Chem, 56:2 (2020), 335
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Alexey P. Krinochkin, Dmitry S. Kopchuk, Kousik Giri, Yaroslav K. Shtaitz, Ekaterina S. Starnovskaya, Igor A. Khalymbadzha, Roman A. Drokin, Eugeny N. Ulomsky, Sougata Santra, Grigory V. Zyryanov, Vladimir L. Rusinov, Oleg N. Chupakhin, “A PASE Approach towards (Adamantyl‐1)‐, Alkyl‐ and (Het)Aryl‐Substituted [1, 2,4]triazolo[1, 5‐d][1, 2,4]triazines: A Sequence of Two Solvent‐Free Reactions Bearing Lower E‐Factors”, ChemistrySelect, 3:28 (2018), 8202
D. S. Kopchuk, A. P. Krinochkin, E. S. Starnovskaya, Ya. K. Shtaitz, I. S. Kovalev, G. V. Zyryanov, V. L. Rusinov, O. N. Chupakhin, “Substitution of Cyano Group in Position 5 of 1,2,4-Triazines by Carboxylic Acid Hydrazide Residues under Solvent-Free Conditions”, Russ J Org Chem, 54:3 (2018), 509
A. P. Krinochkin, D. S. Kopchuk, N. V. Chepchugov, I. S. Kovalev, G. V. Zyryanov, V. L. Rusinov, O. N. Chupakhin, “Effect of substituent in pyridine-2-carbaldehydes on their heterocyclization to 1,2,4-triazines and 1,2,4-triazine 4-oxides”, Russ J Org Chem, 53:7 (2017), 963
A. P. Krinochkin, D. S. Kopchuk, E. S. Starnovskaya, Ya. K. Shtaiz, A. F. Khasanov, I. S. Kovalev, O. S. Taniya, G. V. Zyryanov, V. L. Rusinov, O. N. Chupakhin, “The synthesis of 1,2,4-triazines bearing the residues of higher alcohols in the 5-position via the ipso-substitution of cyano group under the solvent-free conditions”, Chim.Tech.Acta, 4:2 (2017), 112
V. Charushin, V. Rusinov, O. Chupakhin, Comprehensive Heterocyclic Chemistry III, 2008, 95
Dmitry N. Kozhevnikov, Valery N. Kozhevnikov, Tatiana V. Nikitina, Vladimir L. Rusinov, Oleg N. Chupakhin, Igor L. Eremenko, Grigory G. Aleksandrov, “A new route to 6,6′′-dicyano-2,2′:6′,2′′-terpyridines and their complexes with Ni(II)”, Tetrahedron Letters, 43:28 (2002), 4923
Oleg N. Chupakhin, Gennady L. Rusinov, Dmitry G. Beresnev, Valery N. Charushin, Hans Neunhoeffer, “A simple one pot synthesis of condensed 1,2,4‐triazines by using the tandem aN‐SNipso and SNH‐SNipsa reactions”, Journal of Heterocyclic Chem, 38:4 (2001), 901
D. N. Kozhevnikov, A. M. Prokhorov, V. L. Rusinov, O. N. Chupakhin, “Auto-aromatization of the σH-adducts of 1,2,4-triazine 4-oxides with carbanions in reactions of nucleophilic substitution of hydrogen”, Mendeleev Commun., 10:6 (2000), 227–228
D. N. Kozhevnikov, T. V. Nikitina, V. L. Rusinov, O. N. Chupakhin, “The Ritter reaction in the 5-cyano-1,2,4-triazine series”, Mendeleev Commun., 10:3 (2000), 117–118
V. N. Kozhevnikov, D. N. Kozhevnikov, V. L. Rusinov, O. N. Chupakhin, “Nucleophile-induced transformations of 1,2,4-triazines. 3. Anrorc constriction of the ring in the reaction of 6-aryl-3-dimethylamino-1,2,4-triazine 4-oxides with KCN”, Chem Heterocycl Compd, 35:4 (1999), 470
Derek T. Hurst, Progress in Heterocyclic Chemistry, 10, A critical review of the 1997 literature preceded by two chapters on current heterocyclic topics, 1998, 275
O. N. CHUPAKHIN, V. L. RUSINOV, E. N. ULOMSKY, D. N. KOJEVNIKOV, H. NEUNHOEFFER, “ChemInform Abstract: Nucleophilic Substitution of Hydrogen in the Reaction of 1,2,4‐ Triazine‐4‐oxides with Cyanides.”, ChemInform, 28:37 (1997)