aUral Scientific Research Institute of Technology of Medical Preparations, Ekaterinburg, Russian Federation bInstitute of Organic Chemistry, Technical University of Darmstadt, Darmstadt, Germany
Abstract:
Reaction of 6-phenyl-1,2,4-triazine 4-oxide 1a with 1,3-dimethyluracil-6-hydrazones 2a–c in dimethylformamide in the presence of triethylamine affords the pyrazolo[3,4-d]pyrimidines 3a–c; under similar conditions 1,2,4-triazine 4-oxide 1b reacts with 1-phenyl-3-methylpyrazolone 7 to give the hydrazone derivative 8 and the dipyrazolylmethane derivative 9.
Document Type:
Article
Language: English
Citation:
Yu. A. Azev, H. Neunhoeffer, S. Foro, H. J. Lindner, S. V. Shorshnev, “Transformations of 6-Phenyl-1,2,4-triazine 4-Oxides in Reactions with Nucleophiles”, Mendeleev Commun., 5:6 (1995), 229–231
Linking options:
https://www.mathnet.ru/eng/mendc5114
https://www.mathnet.ru/eng/mendc/v5/i6/p229
This publication is cited in the following 18 articles:
Hengchang Ma, Yuan Ma, Jinxia Wang, “The Synthesis of Dipyrazolylmethanes, X-Ray Structure Analysis”, HETEROCYCLES, 89:7 (2014), 1645
Yu. A. Azev, I. S. Kovalev, A. V. Mekhaev, A. M. Gibor, V. I. Baranov, V. A. Bakulev, O. S. Ermakova, “Synthesis, thermal transformations, and mass spectrometric fragmentation of 4,4'-[1,2-bis(5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)ethane-1,2-diyl]-bis(5-methyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one)”, Chem Heterocycl Comp, 49:4 (2013), 545
Yu. A. Azev, E. D. Oparina, I. S. Kovalev, P. A. Slepukhin, R. K. Novikova, “Reactions of quinoxaline with 3-methyl-1-phenylpyrazol-5-one”, Mendeleev Commun., 22:1 (2012), 37–38
Yu. A. Azev, B. V. Golomolzin, S. V. Shorshnev, “Reactions of quinazoline and its 4-oxo- and 4-chloro-substituted derivatives with nucleophiles”, Pharm Chem J, 44:12 (2011), 687
Fung Fuh Wong, Yu-Ying Huang, “Novel Vilsmeier-type methylenation for synthesis of dipyrazolylmethane derivatives using formamide or N-methylformamide”, Tetrahedron, 67:21 (2011), 3863
Wolfgang Holzer, Peter Pfaffenhuemer, Christian Laggner, Stefan Deibl, Barbara Datterl, “Reactions and Tautomeric Behavior of 1-(2-Pyridinyl)-1H-pyrazol-5-ols”, HETEROCYCLES, 83:7 (2011), 1567
Cristina Gómez de la Oliva, Pilar Goya Laza, Carmen Ochoa de Ocariz, Modern Heterocyclic Chemistry, 2011, 1777
Yu. A. Azev, S. V. Shorshnev, “Peculiarities of transformations of unsubstituted quinazoline with C-nucleophiles”, Chem Heterocycl Comp, 45:1 (2009), 115
Yu. A. Azev, T. Duelcks, E. Lork, D. Gabel, “Unusual reactions of 4,6-dichloro-5-nitropyrimidine with C-nucleophiles”, Mendeleev Commun., 15:5 (2005), 193–196
Oleg N Chupakhin, Valery N Kozhevnikov, Anton M Prokhorov, Dmitry N Kozhevnikov, Vladimir L Rusinov, “The amidine rearrangement in 5-amino-6-aryl-1,2,4-triazine-4-oxides initiated by hydroxylamine”, Tetrahedron Letters, 41:38 (2000), 7379
Yu. A. Azev, I. V. Teplyashina, “Reaction of dipyrazolylmethanes with 1-phenyl-3-methylpyrazol-5-one”, Chem Heterocycl Compd, 34:9 (1998), 1091
Yu. A. Azev, I. V. Teplyashina, “Interaction of fervenulin-4-oxide with 1-phenyl-3-methylpyrazol-5-one in the absence of bases”, Pharm Chem J, 32:2 (1998), 97
Yu. A. Azev, I. V. Teplyashina, S. V. Shorshnev, “Unusual reactions of enhydrazinopyrazolones and dipyrazolylmethanes with 5-oxopyrazoles”, Mendeleev Commun., 8:5 (1998), 199–201
Derek T. Hurst, Progress in Heterocyclic Chemistry, 9, 1997, 268
Yu. A. Azev, I. V. Teplyashina, B. V. Golomolzin, “Reaction of 5-azacytosine with 3-methyl-1-phenyl-5-pyrazolone”, Chem Heterocycl Compd, 33:9 (1997), 1114
Yu. A. Azev, “Transformations of 5-azauracil in reactions with some nucleophiles”, Mendeleev Commun., 7:4 (1997), 164–165
YU. A. AZEV, H. NEUNHOEFFER, S. FORO, H. J. LINDNER, S. V. SHORSHNEV, “ChemInform Abstract: Transformations of 6‐Phenyl‐1,2,4‐triazine 4‐Oxides in Reactions with Nucleophiles.”, ChemInform, 27:16 (1996)
Yu. A. Azev, H. Neunhoeffer, S. V. Shorshnev, “Nucleophilic substitution of hydrogen in 3,6-diphenyl-1,2,4-triazine 4-oxide”, Mendeleev Commun., 6:3 (1996), 116–118
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