O-57 One-Step Heterylation at the Upper Rim of Calix[4]arene with 1,2,4-Triazin-5(2H)-ones [Electronic resource] / D. G. Beresnev, N. A. Itsikson, O. N. Chupakhin, V. N. Charushin, M. I. Kodess, A. I. Butakov, G. L. Rusinov, Yu. Yu. Morzherin, A. I. Konovalov, I. S. Antipin // Journal of Organic Chemistry. - 2006. - Vol. 71, № 21. - P8272-8275 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A convenient way to modify calix[4]arenes based on the direct C-C coupling reaction of their phenol moiety with 1,2,4-triazines has been advanced, and the ability of modified calixarenes to provide transport of La3+ and Ga3+ cations through organic membranes has been examined. ?? \\\\Expert2\\nbo\\Journal of Organic Chemistry\\2006, v.71, N 21, p.8272.pdf |
D 62 Direct C-C coupling of meso-octamethylcalix[4]pyrrole with 6-nitroazolopyrimidines [Text] / O. N. Chupakhin, N. A. Itsikson, S. S. Bashirov, D. G. Beresnev, G. L. Rusinov // Heterocycles. - 2005. - № 66. - P543-548 Рубрики: ХИМИЧЕСКИЕ НАУКИ |
A 18 Acid-promoted direct C-C coupling of 1,3-diazines and 1,2,4-triazines with aryl-containing macrocyclic compounds and their open-chain analogues [Text] / N. A. Itsikson, D. G. Beresnev, G. L. Rusinov, O. N. Chupakhin // ARKIVOC. - 2004. - № 12. - P6-13. - Библиогр. : с. 12 (13 назв.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A method of direct C-C coupling of azahetarenes with macrocycles (calix[4]arene, benzo-12-??crown-4, 1,5-bis(2,6-dimethylphenoxy)-3-oxapentane), based on the nucleophilic addition to ??unsubstituted carbon atom in azines, has been developed. |
D 62 Direct C-C coupling of ferrocenyllithium and azaheterocycles by nucleophilic substitution of hydrogen - synthesis of mono- and 1,1'-diazinylferrocenes [Text] / O. N. Chupakhin, I. A. Utepova, I. S. Kovalev, V. L. Rusinov, Z. A. Starikova // European Journal of Organic Chemistry. - 2007. - № 5. - P857-862 Рубрики: ХИМИЧЕСКИЕ НАУКИ |
S 98 Synthesis, analgesic and antipyretic activity of 2-(antipyrin-4-yl)hydrazones of 1,2,3-triketones and their derivatives [Electronic resource] / E. V. Shchegol'kov, O. G. Khudina, L. V. Anikina, Ya. V. Burgart, V. I. Saloutin // Pharmaceutical Chemistry Journal. - 2006. - Vol. 40, № 7. - P373-376. - Библиогр. : с. 376 (10 назв.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: 1,2,3-Triketone 2-(antipyrin-4-yl)hydrazones were synthesized via the azo-coupling reactions of 1,3-diketones with 2-(antipyrin-4-yl)diazonium chloride. The fluoroalkyl-containing hetarylhydrazone enters into cyclocondensation with hydrazines at the 1,3-dicarbonyl fragment to yield 3-tetrafluoroethyl derivatives of pyrazole. It was found that 1,2,3-triketone 2-(antipyrin-4-yl)hydrazones and N-(2-hydroxyethyl)-substituted pyrazole exhibit analgesic activity comparable with that of their structural analog analgin (metamizole sodium), but do not possess antipyretic properties. In contrast, N-phenyl-substituted pyrazole did not exhibit analgesic properties but produced a certain antipyretic effect four hours after pyrogenic administration. Fluoroalkyl-containing compounds are less toxic substances than nonfluorinated 2-(antipyrin-4-yl)hydrazone and analgin. \\\\Expert2\\nbo\\Pharmaceutical Chemistry Journal\\2006, 40 (7), 373-376.pdf |
S 98 Synthesis and the reactions of trifluoromethylated 1,2,3-triketones 2-(het)arylhydrazones and 4,7-dihydroazolo[5,1-c]triazines [Electronic resource] / O. G. Khudina, E. V. Shchegol'kov, Ya. V. Burgart, M. I. Kodess, O. N. Kazheva, A. N. Chekhlov, G. V. Shilov, O. A. Dyachenko, V. I. Saloutin, O. N. Chupakhin // Journal of Fluorine Chemistry. - 2005. - Vol. 126, № 8. - P1230-1238 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The coupling of trifluoromethylated 1,3-diketones with (het)aryldiazonium chlorides results mainly in the formation of 1,2,3-triketones 2-(het)arylhydrazones while using hetarylamine with a NH-group at the ?-position of the heterocycle as the diazonium component gives 4,7-dihydroazolo[5,1-c]triazines due to cyclization at the trifluoroacetyl fragment. Trifluoromethylated 1,2,3-triketones 2-(het)arylhydrazones and 7-hydroxy-4,7-dihydroazolo[5,1-c]triazines react regio-selectively with methyl hydrazine and phenyl hydrazine to form 3-CF3-pyrazoles. The long-range coupling constants (JF-H) of 1-methylpyrazoles and the chemical shifts of trifluoromethyl groups in the 19F NMR spectra can be used for the determination of regio-isomeric structures of mono(trifluoromethyl)-substituted pyrazoles. 2-(Het)arylhydrazones and 4,7-dihydroazolo[5,1-c]triazines with two trifluoromethyl substituents afford the mixtures of cis- and trans-azopyrazoles in the reactions with hydrazines. \\\\Expert2\\nbo\\Journal of Fluorine Chemistry\\2005, v.126, p.1230.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). |
F 98 Fused fluoroquinolones: synthesis and 1H and 19F NMR studies [Text] / V. N. Charushin, E. V. Nosova, G. N. Lipunova, M. I. Kodess // Journal of Fluorine Chemistry. - 2001. - Vol. 110, № 1. - P25-30. - Bibliogr. : p. 30 (19 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: New derivatives of fused fluoroquinolones bearing five aromatic rings have been obtained. The 19F NMR spectra of these pentacyclic fluoroquinolones demonstrate unusual through space 1H–19F and 19F–19F spin–spin interactions with coupling constants 6J(F, H)=2.0–3.0 Hz, 7J(F, F)=3.5–4.0 Hz and 9J(F, H)=3.0–3.5 Hz. Relative reactivities of fluorine atoms in pentacyclic fluoroquinolones in the amino-defluorination reactions are also different relative to bi- and tricyclic fluoroquinolones???? \\\\Expert2\\nbo\\Journal of Fluorine Chemistry\\2001.v.110. p. 25.pdf |
T 44 The first case of direct coupling of heterocycles with calixarenes. Reaction of resorcinarenes with 1,2,4-triazin-5(2H)-ones [Text] / O. N. Chupakhin, G. L. Rusinov, N. A. Itsikson, D. G. Beresnev, I. L. Nikolaeva, A. R. Burilov, A. I. Konovalov // Heterocyclic Communications. - 2004. - Vol. 10, № 1. - P15-18 : ил. - Библиогр.: с. 18 (8 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): CALIXARENE -- CARBON -- RESORCINOL DERIVATIVE -- TRIAZINE DERIVATIVE Аннотация: A convenient method for an one-step coupling of resorcinarenes with 3-R-1,2,4-triazin-5(2H)-ones, involving nucleophilic addition to the unsubstituted carbon atom C-6 of triazine ring, has been worked out. |
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 62 Direct introduction of heterocyclic units into porphyrin derivatives [Electronic resource] / O. N. Chupakhin, G. L. Rusinov, D. G. Beresnev, S. Sh. Bashirov, M. G. P. M. S. Neves, J. A. S. Cavaleiro // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2004. - Vol. 53, № 1. - P160-163 : ил. - Библиогр.: с. 163 (10 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): 1,2,4-TRIAZHIES -- HETERYLPORPHYRINS -- MESO-TETRAARYLPORPHYRINS -- NONSYMMETRICAL PORPHYRINS -- QUINAZOLINE Аннотация: In the reaction with quinazoline and 5-phenyl-1,2,4-triazin-5(2H)-one, 5,10,15,20-tetra(4-methoxyphenyl)porphyrin exhibits nucleophilic properties. In quinazoline excess, C-C coupling occurs at the C=N bond of azines and position 3 of the aryl ring to form 5,10,15,20-tetrakis(3-heteryl-4-methoxyphenyl) porphyrins. Monoheteryl-substituted porphyrin was obtained by the reaction of equimolar amounts of 5,10,15,20-tetra(4-methoxyphenyl)porphyrin and 5-phenyl-1,2,4-triazin-5(2H)-one. \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2004, 53 (1), 160.pdf |
S 10 S-N(H) Reactions of ferrocenyllithium and azine N-oxides [Text] / O. N. Chupakhin, M. V. Varaksin, I. A. Utepova, V. L. Rusinov // ARKIVOC. - 2009. - Vol. 2009, № 6. - P208-220 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A non-catalytic C-C coupling of ferrocenyllithium and heterocyclic N-oxides 2 was carried out for the first time using the reaction of nucleophilic substitution of hydrogen (SNH) in azines |
R 30 Reactions of radicals generated from 1-ethyl-1,4-diazinium salts: Addition to the C-C triple bond versus dimerization [Text] / G. L. Rusinov, E. V. Verbitskiy, P. A. Slepukhin, O. N. Zabelina, M. I. Kodess, M. A. Ezhikova, V. N. Charushin, O. N. Chupakhin // Heterocycles. - 2009. - Vol. 78, № 9. - P2315-2324 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Radical species generated from 5-aryl-substituted 1-ethyl-2,3-dicyano-1,4-diazinium salts by action of sodium iodide undergo dimerization into [2,2?]bipyrazinyl derivatives, as evidenced by NMR and X-ray crystallography data. The pyrazinyl radicals can also be involved into the addition reaction on the C-C triple bond, thus demonstrating a new synthetic route to modify the structure of pyrazines. The structures of E- and Z-isomers of 1-(1?,2?-dihydropyrazinyl-2?)-2-iodoethenes have been proved by 1H and 13C NMR spectroscopy and X-ray analysis |
S 98 Synthesis of fluorinated 2(3)-arylhydrazones of 1,2,3-tri(1,2,3,4-tetra)carbonyl compounds and their heterocyclization reactions [] / Ya. V. Burgart, A. S. Fokin, O. G. Kuzueva, O. N. Chupakhin, V. I. Saloutin // Journal of Fluorine Chemistry. - 1998. - Vol. 92, № 2. - С. 101-108 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: New fluorinated 2-arylhydrazones of 1,2,3-triketones, 2-arylhydrazone-1,2,3-diketo esters and 3-arylhydrazone-1,2,3,4-triketo esters have been prepared by the coupling of fluorine-containing 1,3-keto esters, 1,3-diketones, acyl(aroyl)pyruvic esters and their chelates with aryldiazonium chlorides. The arylhydrazones react with hydrazine hydrate, phenylhydrazine, thiosemicarbazide and hydroxylamine to form the corresponding pyrazole and isoxazole derivatives. Interaction of 3-arylhydrazone-1,2,3,4-diketo esters with o-phenylenediamine results in quinoxaline products. Intramolecular cyclization of the arylhydrazones with pentafluorophenyl substituents leads to cinnolone derivatives |
G 37 Geometric isomerism in the series of fluoroalkyl-containing 1,2,3-trione 2-arylhydrazones [Electronic resource] / O. G. Khudina, E. V. Shchegol'kov, M. I. Kodess, Ya. V. Burgart, V. I. Saloutin, O. N. Chupakhin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2007. - Vol. 43, № 3. - P380-387 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): 2-ARYLHYDRAZONES -- X-RAY DIFFRACTION Аннотация: According to the 1H, 13C, and 19F NMR data, fluoroalkyl-containing 1,2,3-trione 2-arylhydrazones in CDCl3 exist exclusively, while in (CD3)2CO preferentially, as isomers in which the acyl or aroyl group is involved in intramolecular hydrogen bond. The isomer structure was assigned on the basis of the chemical shifts of the carbonyl carbon atoms and fluorine atoms and carbon-fluorine spin-spin coupling constants J C-F. X-Ray diffraction data showed that 1,2,3-trione 2-arylhydrazones in crystal have the same structure as in CDCl3 solution. Quantum-chemical calculations were performed to rationalize predominant formation of 1,2,3-trione 2-arylhydrazone isomers with a free polyfluoroacyl group \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2007, 43 (3), 380-387.pdf |
S 98 Synthesis and structure of 4-hydroxy-4-fluoroalkyl-1,4-dihydroimidazo[5,1-c][1,2,4]triazines [Electronic resource] / E. V. Shchegol'kov, E. V. Sadchikova, Ya. V. Burgart, V. I. Saloutin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2009. - Vol. 45, № 4. - P572-580 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Azo coupling of fluorinated 1,3-diketones with 4-ethoxycarbonyl-1H-imidazole-5-diazonium chloride led to the formation of 4-hydroxy-4-polyfluoroalkyl-1,4-dihydroimidazo[5,1-c][1,2,4]triazines. According to the 1H and 19F NMR data, these compounds in solution give rise to ring-chain tautomerism via opening of the C4-N5 bond, which is especially characteristic of dihydroimidazotriazines with a polyfluoroalkyl substituent longer than trifluoromethyl group \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2009, 45 (4), 572.pdf |
S 98 Synthesis, structure, and complexing ability of fluoroalkyl-containing 2,2-(biphenyl-4,4-diyldihydrazono)bis(1,3-dicarbonyl) compounds [Electronic resource] / I. V. Shchur, O. G. Khudina, Ya. V. Burgart, V. I. Saloutin, M. A. Grishina, V. A. Potemkin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2007. - Vol. 43, № 12. - P1781-1787 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: New fluoroalkyl-containing 2,2?-(biphenyl-4,4?-diyldihydrazono)bis(1,3-diketones) and 2,2?-(biphenyl-4,4?-diyldihydrazono)bis(3-oxopropionates) were synthesized by azo coupling of the corresponding 1,3-dicarbonyl compounds with biphenyl-4,4?-bis(diazonium) dichloride. Complexing ability of the obtained bis-hydrazones was studied, and new coordination compounds of the general formula M2L2 [where M = Ni(II), Cu(II); L = fluoroalkyl-containing 2,2?-(biphenyl-4,4?-diyldihydrazono)bis(1,3-diketone)] were obtained \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2007, 43 (12), 1781.pdf |
K 96 Kuzueva, O. G. Synthesis of 2-arylhydrazones of aliphatic fluorine-containing 1,2,3-tricarbonyl compounds and their reactions with dinucleophiles [Electronic resource] / O. G. Kuzueva, Ya. V. Burgart, V. I. Saloutin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 1998. - Vol. 47, № 4. - P673-678 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: New fluorinated 2-arylhydrazones of 1,2,3-tricarbonyl compounds were obtained by coupling fluorine-containing 3-oxo esters, 1,3-diketones, and their copper chelates with aryldiazonium chlorides. Reactions of these arylhydrazones with hydrazine hydrate, phenylhydrazine, thiosemicarbazide, and hydroxylamine gave the corresponding pyrazole and isoxazole derivatives \\\\Expert2\\nbo\\Russian Chemical Bulletin\\1998, 47 (4), 673.pdf |
S 98 Synthesis of fluoroalkyl-containing 1,2,3-triketone 2-hetarylhydrazones and their reactions with hydrazines [Electronic resource] / E. V. Shchegol'kov, Ya. V. Burgart, O. G. Khudina, V. I. Saloutin, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2004. - Vol. 53, № 11. - P2584-2590 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Fluoroalkyl-containing 1,2,3-triketone 2-(2,3-dimethyl-5-oxo-1-phenyl-1,2-dihydropyrazol-4-yl)-, 2-(4-ethoxycarbonylpyrazol-3-yl)-, and 2-(1,2,4-triazol-3-yl)hydrazones were synthesized by the azo coupling reactions of fluorinated 1,3-diketones with the corresponding hetaryldiazonium chlorides. The hetarylhydrazones thus synthesized were subjected to cyclocondensation with hydrazines at the 1,3-dicarbonyl fragment to give 3-fluoroalkyl-4-hetarylazopyrazoles \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2004, 53 (11), 2584-2590.pdf |
P 93 Protolytic Equilibria of Some N,N-Bis(2-carboxyethyl)aminoazobenzenesulfonic Acids in Aqueous Solution [Electronic resource] / Yu. A. Skorik, L. K. Neudachina, A. V. Osintsev, Yu. G. Yatluk, A. A. Vshivkov, E. V. Osintseva // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2002. - Vol. 38, № 3. - P385-389 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: 4-[4-Bis(2-carboxyethyl)aminophenylazo]benzenesulfonic acid and 4-[2-bis(2-carboxyethyl)amino-4,5-dimethylphenylazo]benzenesulfonic acid were synthesized for the first time by azo coupling of diazosulfanilic acid with N,N-bis(2-carboxyethyl)aniline and N,N-bis(2-carboxyethyl)-3,4-xylidine, respectively. The acid ionization constants of the products were determined, their electron absorption spectra were measured, and schemes of acid-base equilibria in aqueous solution were proposed \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2002, 38 (3), 385.pdf |