О-42 1,2,4-triazinones in Interactions with C-nucleophiles [Text] : доклад, тезисы доклада / O. N. Chupakhin, G. V. Zyryanov, T. L. Pilicheva, V. L. Rusinov // International Memorial I.Postovsky Conference on Organic Chemisty, Ekaterinburg, March 17-20, 1998 : program and abstracts. - Ekaterinburg, 1998. - P149 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): 1.2.4-ТРИАЗИНОНЫ -- ВЗАИМОДЕЙСТВИЕ ХИМИЧЕСКОЕ -- ХИМИЧЕСКОЕ ВЗАИМОДЕЙСТВИЕ -- НУКЛЕОФИЛЫ -- C-НУКЛЕОФИЛЫ -- КОНФЕРЕНЦИИ -- ТЕЗИСЫ ДОКЛАДОВ -- ОРГАНИЧЕСКАЯ ХИМИЯ -- ХИМИЯ ОРГАНИЧЕСКАЯ |
A 89 Asymmetric induction in the reactions of 3-aryl-1,2,4-triazin-5(4H)-ones with C-nucleophiles [Electronic resource] / I. N. Egorov, G. V. Zyryanov, E. N. Ulomskii, V. L. Rusinov, O. N. Chupakhin // Tetrahedron Letters. - 2006. - Vol. 47, № 42. - P7485-7487 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: 3-Aryl-1,2,4-triazin-5(4H)-ones, in the presence of N-protected amino acids, react with C-nucleophiles to form 1-acyl-6-Nu-3-aryl-1,6-dihydro-1,2,4-triazin-5(4H)-ones in high diastereomeric excess. This is the first case of the use of amino acids as chiral auxiliaries in nucleophilic additions to triazinones. \\\\Expert2\\nbo\\Tetrahedron Letters\\2006, v. 47, p.7485.pdf |
D 62 Direct modification of benzoannelated crown ethers with 1,2,4-triazin-5(2H)-one moieties [Text] / G. L. Rusinov, D. G. Beresnev, N. A. Itsikson, O. N. Chupakhin // Heterocycles. - 2001. - Т. 55, № 12. - P2349-2359 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A convenient method for one-step coupling of benzoannelated crown ethers with 1,2,4-triazinones based on the reaction of nucleophilic addition to unsubstituted carbon atom of the triazine ring has been worked out. It has been shown that the reaction of 3-substituted 1,2,4-triazin-5(2H)-ones (1) with benzocrown ethers (benzo-12-crown-4, benzo-15-crown-5, benzo-18-crown-6) in the presence of acetic or trifluoroacetic anhydride is accompanied by acylation of triazine ring and results in formation of 3-(1-acyl-5-oxo-1,4,5,6-tetrahydro-1,2,4-triazin-6-yl)benzocrown ethers (7-12). The latters were converted to 3-(5-oxo-2,5-dihydro-1,2,4-triazin-6-yl)benzocrown ethers (18-20) using two alternative routes: the elimination of acetic or trifluoroacetaldehyde or the deacylation followed by the oxidation of the 1,4,5,6-tetrahydro derivatives (13-15). |
C 57 Chupakhin, O. N. One-step hetarylation of steroids: regioselective synthesis of new estrone derivatives [Electronic resource] / O. N. Chupakhin, D. G. Beresnev, N. A. Itsikson // Mendeleev Communications. - 2006. - Vol. 16, № 2. - P95-96 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: New estrone derivatives containing 1,2,4-triazin-5-one moieties were synthesised through direct CC coupling of estrone 3-methyl ether with 1,2,4-triazinones \\\\Expert2\\nbo\\Mendeleev Communications\\2006, v.16, p.95.pdf |
D 53 Diastereoselective synthesis of 3-substituted acylamino-3,4-dihydro-1,2,4-triazinones [Electronic resource] / I. N. Egorov, B. Konig, V. L. Rusinov, O. N. Chupakhin // Mendeleev Communications. - 2008. - Vol. 18, № 2. - P99-101 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: 6-Phenyl-1,2,4-triazin-5(4H)-one 1 reacts with C-nucleophiles, such as indole, in the presence of N-acetylamino acids, to yield 2-acyl-3-indolyl-6-phenyl-3,4-dihydro-1,2,4-triazin-5(4H)-ones 2–6 with high diastereoselectivity \\\\Expert2\\nbo\\Mendeleev Communications\\2008, v.18, p.99.pdf |
T 19 Tandem AN—AN reactions in the synthesis of 1H-pyrrolo[3,2-e]-1,2,4-triazines and products of their oxidative transformations [Electronic resource] / V. N. Charushin, N. N. Mochul`skaya, A. A. Andreiko, M. I. Kodess, I. A. Litvinov, O. G. Sinyashin, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2003. - Vol. 52, № 8. - P1740-1749 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The reactions of 3-aryl-1,2,4-triazines with -aminovinyl ketones or ethyl -aminocrotonates in acetic anhydride at room temperature afforded cyclic products of the tandem nucleophilic addition, viz., 3a,4,7,7a-tetrahydro-1H-pyrrolo[3,2-e]-1,2,4-triazines, in good yields. Under oxidative conditions, the latter compounds underwent the pyrrole-ring opening under the action of potassium permanganate to form the corresponding triazinones and were transformed into thriazolyl-substituted pyridines under the action of selenious acid \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2003, 52 (8), 1740.pdf |
A 99 Azolo[5,1-c]-1,2,4-triazines as a new class of antiviral compounds [Electronic resource] / V. L. Rusinov, E. N. Ulomskii, V. N. Charushin, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2008. - Vol. 57, № 5. - P985-1014 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Synthetic methods, reactivity, and the properties of a new class of antiviral compounds, pyrazolo-, imidazo-, 1,2,4-triazolo[5,1-c]-1,2,4-triazinones, tetrazolo[5,1-b]-1,2,4-triazinones, and azoloannulated amino-1,2,4-triazines having structural similarity with biogenic purines and capable of mimicking them in metabolic processes are considered \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2008, 57 (5), 985.pdf |
N 52 New 1,2,4-triazine-containing podands: synthesis and properties [Electronic resource] / O. N. Chupakhin, G. L. Rusinov, N. A. Itsikson, D. G. Beresnev, O. V. Fedorova, I. G. Ovchinnikova // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2004. - Vol. 53, № 10. - P2308-2313 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A method of one-step C-C coupling of 1,5-bis(2,6-dimethylphenoxy)-3-oxapentane (1a) and 1,8-bis(2,6-dimethylphenoxy)-3,6-dioxaoctane (1b) with 3-methylthio- (2) and 3-amino-1,2,4-triazine (3) and 3-aryl-1,2,4-triazin-5-one (6-8) has been described. The reaction of compounds 1a,b with compounds 2 and 3 in the presence of trifluoroacetic acid results in the addition of the dimethylphenoxy group to the unsubstituted C(5) carbon atom of the triazine ring. The reactions of triazinones 6-8 with compounds 1a,b in a mixture of trifluoroacetic acid and organic anhydrides are accompanied by the acylation of the nitrogen atom adjacent to the reaction center and affords bis[(3-R-1-acyl-5-oxo-1,4,5,6-tetrahydro-1,2,4-triazin-6-yl)-2,6-dimethylphenoxy]-3-oxapentane or -3,6-dioxaoctane. The obtained adducts can smoothly be oxidized under mild conditions to form more stable products of nucleophilic hydrogen substitution in the triazine ring. The extraction and transport of Ca2+ and Mg2+ cations through an organic membrane by the compounds synthesized are discussed. \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2004, 53 (10), 2308.pdf |
A 89 Asymmetric induction in the reactions of azinones with C-nucleophiles [Electronic resource] / O. N. Chupakhin, I. N. Egorov, V. L. Rusinov, P. A. Slepukhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2010. - Vol. 59, № 5. - P991-1001 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): TRIAZINONES -- QUINOXALIN -- C-NUCLEOPHILES -- INDOLES Аннотация: Effect of acylating agents on the course of addition of C-nucleophiles to 1,2,4- and 1,3,5-triazinones, as well as to quinoxalin-2(1H)-one, was studied. A series of new azinone derivatives was obtained. A method for the preparation of diastereomerically pure addition products of indoles to 1,2,4-triazinones and quinoxalin-2(1H)-one in the presence of N-Ts-L-amino acid acyl chlorides was suggested \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2010, 59 (5), 991-1001.pdf |
E 31 Egorov, I. N. Asymmetric induction in reactions of chiral acylazinium salts (review) [Электронный ресурс] / I. N. Egorov, V. L. Rusinov, O. N. Chupakhin // Chemistry of Heterocyclic Compounds. - 2012. - Vol.48, №5. - P684-697 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): 1,2,4-TRIAZINES -- ACYLAZINIUM SALTS -- ASYMMETRIC INDUCTION Аннотация: The effectiveness of asymmetric induction in the reactions of chiral acylazinium salts produced from pyridines, quinolines, isoquinolines, 1,2,4-triazinones, and a series of chiral acylating agents is analyzed \\\\Expert2\\NBO\\Chemistry of Heterocyclic Compounds\\2012, v.48, N 5, p.684-697.pdf |