Abstract:
Treatment of 3-oxo-, 3-thioxo- and 3-imino-5,7-dimethyl-4a,7a-diphenylperhydroimidazo[4,5-e][1,2,4]triazin-6-ones with NaNO2 in the presence of AcOH caused contraction of the perhydrotriazine cycle to the imidazolidine one. The products were transformed into glycolurils and their analogues.
Document Type:
Article
Language: English
Citation:
A. N. Kravchenko, G. A. Gazieva, S. V. Vasilevskii, P. A. Belyakov, Yu. V. Nelyubina, “HNO2-Assisted Triazine Cycle Contraction in 3-oxo-,3-thioxo- and 3-imino-5,7-dimethyl-4a,7a-diphenyl-perhydroimidazo[4,5-e][1,2,4]triazin-6-ones”, Mendeleev Commun., 22:6 (2012), 299–301
Linking options:
https://www.mathnet.ru/eng/mendc2827
https://www.mathnet.ru/eng/mendc/v22/i6/p299
This publication is cited in the following 8 articles:
Vladimir V. Baranov, Anton A. Galochkin, Yulia V. Nelyubina, Angelina N. Kravchenko, Nina N. Makhova, “Synthesis and Structure of 1-Substituted Semithioglycolurils”, Synthesis, 52:17 (2020), 2563
N. N. Makhova, L. I. Belen'kii, G. A. Gazieva, I. L. Dalinger, L. S. Konstantinova, V. V. Kuznetsov, A. N. Kravchenko, M. M. Krayushkin, O. A. Rakitin, A. M. Starosotnikov, L. L. Fershtat, S. A. Shevelev, V. Z. Shirinian, V. N. Yarovenko, “Progress in the chemistry of nitrogen-, oxygen- and sulfur-containing heterocyclic systems”, Russian Chem. Reviews, 89:1 (2020), 55–124
Angelina N. Kravchenko, Sergei V. Vasilevskii, Galina A. Gazieva, Vladimir V. Baranov, Valery A. Barachevsky, Olga I. Kobeleva, Olga V. Venidiktova, Valentina A. Karnoukhova, “Transformations of S-substituted 5,7-dimethyl-4a,5a-diphenyl-3-thioxoperhydroimidazo[4,5-e]-1,2,4-triazin-2-ones under treatment of 1,2-benzoquinones and photochemical properties of reaction products”, Tetrahedron, 74:19 (2018), 2359
A. N. Kravchenko, V. V. Baranov, G. A. Gazieva, “Synthesis of glycolurils and their analogues”, Russian Chem. Reviews, 87:1 (2018), 89–108
G. A. Gazieva, T. B. Karpova, T. V. Nechaeva, A. N. Kravchenko, “Ring contraction of 1,2,4-triazine derivatives in the synthesis of imidazoles”, Russ Chem Bull, 65:9 (2016), 2172
Vladimir V. Baranov, Yulia V. Nelyubina, Angelina N. Kravchenko, Natalya G. Kolotyrkina, Ksenia A. Biriukova, “New access to thioglycolurils by condensation of 4,5-dihydroxyimidazolidin-2-ones(thiones) with HSCN”, Tetrahedron Letters, 56:44 (2015), 6085
Galina A. Gazieva, Angelina N. Kravchenko, “Unexpected Formation of Thioglycolurils Precursors”, J. Heterocyclic Chem., 52:6 (2015), 1858
Angelina N. Kravchenko, Galina A. Gazieva, Sergei V. Vasilevskii, Pavel A. Belyakov, Yulia V. Nelyubina, “ChemInform Abstract: HNO2‐Assisted Triazine Cycle Contraction in 3‐Oxo‐, 3‐Thioxo‐ and 3‐Imino‐5,7‐dimethyl‐4a,7a‐diphenylperhydroimidazo[4,5‐e] [1,2,4]triazin‐6‐ones.”, ChemInform, 44:16 (2013)
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