О-42 1-Alkyl-1,2,4-triazinium ylides as 1,3-dipoles in a cycloaddition reaction with diethyl acetylenedicarboxylate [Electronic resource] / O. N. Chupakhin, B. V. Rudakov, S. G. Alexeev, S. V. Shorshnev, V. N. Charushin // Mendeleev Communications. - 1992. - N 3. - P85-86 . - ISSN 0959-9436 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): 1-АЛКИЛ-1.2.4-ТРИАЗИНИЛИДЫ -- ИЛИДЫ -- ДИПОЛИ -- 1.3-ДИПОЛИ -- ЦИКЛОПРИСОЕДИНЕНИЕ -- ДИЭТИЛАЦЕТИЛЕНДИКАРБОКСИЛАТ -- ДЕПРОТОНАЦИЯ -- 1-АЛКИЛ-5-ФЕНИЛ-1.2.4-ТРИАЗИНА СОЛИ -- триэтиламины -- АЗОМЕТИНИЛИДЫ -- ЦИКЛОПРИСОЕДИНЕНИЕ ДИПОЛЯРНОЕ -- ДИПОЛЯРНОЕ ЦИКЛОПРИСОЕДИНЕНИЕ -- ПИРРОЛО[2.1-F]1.2.4-ТРИАЗИНЫ -- СОЛИ -- ОРГАНИЧЕСКАЯ ХИМИЯ -- ХИМИЯ ОРГАНИЧЕСКАЯ Аннотация: Deprotonation of 1-alkyl-5-phenyl-1,2,4-triazinium salts by triathylamine results in the formation of azomethyne ylides which undergo a 1,3-dipolar cycloaddition reaction with diethyl acetylenedicarboxylate to yield pyrrolo[2,1-f]1,2,4-triazines |
H 99 Interaction of 5-methoxy-1,2,4-triazines with ureas as a new route to 6-azapurines [Electronic resource] / D. G. Beresnev, G. L. Rusinov, O. N. Chupakhin, H. Neunhoeffer // Mendeleev Communications. - 2000. - Vol. 10, N 2. - P58-59 . - ISSN 0959-9436 Рубрики: ХИМИЧЕСКИЕ НАУКИ |
N 91 Nucleophilic Substitution of the Cyano Group in 1,2,4-triazines [Text] : доклад, тезисы доклада / O. N. Chupakhin, I. S. Kovalev, V. N. Kozhevnikov, D. N. Kozhevnikov, V. L. Rusinov // International Memorial I.Postovsky Conference on Organic Chemisty, Ekaterinburg, March 17-20, 1998 : program and abstracts. - Ekaterinburg, 1998. - P78 Рубрики: ХИМИЧЕСКИЕ НАУКИ |
H 99 Interaction of 5-methoxy-1,2,4-triazines with Urea: a New Way to the Synthesis of Azapurine Derivatives [Text] : доклад, тезисы доклада / D. G. Beresnev, G. L. Rusinov, O. N. Chupakhin, H. Neunhoeffer // International Memorial I.Postovsky Conference on Organic Chemisty, Ekaterinburg, March 17-20, 1998 : program and abstracts. - Ekaterinburg, 1998. - P50 Рубрики: ХИМИЧЕСКИЕ НАУКИ |
C 73 Condensed 1,2,4-Triazines from the Reaction of 5-methoxy-1,2,4-triazinium Salts with 1,3-dinucleophiles [Text] : доклад, тезисы доклада / D. G. Beresnev, G. L. Rusinov, O. N. Chupakhin, H. Neunhoeffer // International Memorial I.Postovsky Conference on Organic Chemisty, Ekaterinburg, March 17-20, 1998 : program and abstracts. - Ekaterinburg, 1998. - P49 Рубрики: ХИМИЧЕСКИЕ НАУКИ |
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 |
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. |
F 94 From 1,2,4-triazines towards Substituted pyridines and their cyclometalled Pt complexes [Electronic resource] / V. N. Kozhevnikov, M. M. Ustinova, P. A. Slepukhin, D. N. Kozhevnikov, Amedeo Santoro, W. Dunkan // Tetrahedron Letters. - 2008. - Vol. 49, № 26. - P4096-4098 : рис. - Библиогр. : с. 4098 (28 назв.) . - ISSN 0040-4039 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A new, efficient methodology for the synthesis of substituted thienylpyridines includes the synthesis of 3-thienyl-1,2,4-triazines using simple heterocyclisation followed by easy transformation of the triazine ring to a pyridine through an aza Diels–Alder approach. A variety of substituted pyridines can be easily achieved using cheap, commercially available reagents such as bromoacetylarenes, aroyl hydrazides, norbornadiene, and enamines in various combinations. New thienylpyridines form phosphorescent cyclometallated Pt complexes.?? \\\\Expert2\\nbo\\Tetrahedron Letters\\2008, v. 49, p.4096.pdf |
F 12 Facile Synthesis of 6-aryl-3-pyridyl-1,2,4-triazines as a key step towards hightly fluorescent 5-substituted bipyridines and their Zn(II) and Ru(II) complexes [Electronic resource] / V. N. Kozhevnikov, O. V. Shabunina, D. S. Kopchuk, M. M. Ustinova, B. Konig, D. N. Kozhevnikov // Tetrahedron. - 2008. - Vol. 64, № 37. - P8963-8973 : рис., табл. - Библиогр. : с. 8973 (21 назв.) . - ISSN 0040-4020 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A wide series of substituted bipyridines were obtained through the synthesis of 1,2,4-triazines and their aza Diels–Alder reactions. The reported method facilitates the synthesis of functionally diverse bipyridines that provides fine-tuning of photophysical properties of new ligands and their Zn(II) and Ru(II) complexes. Some of substituted bipyridines exhibit ‘off–on’ fluorescence response toward Zn2+ cations.???? \\\\Expert2\\nbo\\Tetrahedron\\2008, v. 64, N37, p. 8963.pdf |
Д 26 9-Allyl-1,7-dicarbadodecaborane as a dienophile in aza Diels-Alder reactions of 1,2,4-triazines: synthesis of pyridines bearing a carborane cage [Electronic resource] / A. M. Prokhorov, P. A. Slepukhin, V. L. Rusinov, V. N. Kalinin, D. N. Kozhevnikov // Tetrahedron Letters. - 2008. - Vol. 49, № 23. - P3785-3789 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): TRIAZINES -- PYRIDINES Аннотация: The synthesis of pyridine and bipyridine derivatives of m-carborane via aza Diels–Alder reaction of 1,2,4-triazines with 9-allyl m-carborane and their structural characterization and photophysical properties are described. The products 3- and 4-(m-carborane-9-ylmethyl)-2,2`-bipyridines form Zn(II) complexes on reaction with ZnCl2, which increases significantly their fluorescence intensity. \\\\Expert2\\nbo\\Tetrahedron Letters\\2008, v. 49, p.3785.pdf |
F 94 From 3-chloromethyl-1,2,4-triazine 4-oxides to various substituted pyridines and 1,2,4-triazines [Electronic resource] / V. N. Kozhevnikov, D. N. Kozhevnikov, O. V. Shabunina, N. N. Kataeva, S. A. Yushchuk, V. L. Rusinov, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2005. - Vol. 54, № 9. - P2187-2196. - Библиогр. : с. 2196 (24 назв.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: An efficient strategy for the synthesis of new pyridine and 1,2,4-triazine derivatives starting from available 6-aryl-3-chloromethyl-1,2,4-triazine 4-oxides was proposed. The deoxygenative nucleophilic hydrogen substitution in the triazine-oxide ring, nucleophilic substitution of the chlorine atom in the side chain, and transformations of the 1,2,4-triazine ring into the pyridine ring via the inverse-electron-demand Diels-Alder reactions, being used in different orders, are a rather flexible tool for the functionalization of the titled heterocycles. The cyanide anion, indoles, thiophenols, amines, and triphenylphosphine were used as nucleophiles. The direct introduction of indole residues into the 1,2,4-triazine ring followed by the substitution of the chlorine atom by a residue of the primary or secondary aliphatic amine was found to be the most convenient method for the library synthesis. \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2005, 54 (9), 2187-2196.pdf |
T 82 Transformations of 1,2,4-triazine 4-oxides to pyridazines and triazolo[4,3-b]pyridazines by the action of substituted acetonitriles [Electronic resource] / D. N. Kozhevnikov, N. N. Kataeva, V. L. Rusinov, O. N. Chupakhin, G. G. Aleksandrov // Mendeleev Communications. - 2005. - Vol. 15, № 1. - P31-33 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Two types of ring transformations of 1,2,4-triazine to pyridazine were found: 1,2,4-triazine 4-oxides bearing ortho-halophenyl in the 3-position react with phenylacetonitrile under basic conditions to form 3-(2-oxyphenyl)[1,2,4]triazolo[4,3-b]pyridazines, while the reactions of 3,6-diaryl-1,2,4-triazin 4-oxides with sodium ethyl cyanoacetate afforded 2-aminopyridazines. \\\\Expert2\\nbo\\Mendeleev Communications\\2005, v.15, p.31.pdf |
A 53 An efficient route to 5-(hetero)aryl-2,4'- and 2,2'-bipyridines through readily available 3-pyridyl-1,2,4-triazines [Electronic resource] / V. N. Kozhevnikov, D. N. Kozhevnikov, O. V. Shabunina, V. L. Rusinov, O. N. Chupakhin // Tetrahedron Letters. - 2005. - Vol. 46, № 11. - P1791-1793 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A new route to substituted bipyridines based on a new method for the synthesis of substituted 3-pyridyl-1,2,4-triazines and their aza-Diels-Alder reactions is shown to be an efficient strategy for the preparation of structurally diverse bipyridine ligands. \\\\Expert2\\nbo\\Tetrahedron Letters\\2005, v. 46, p.1791.pdf |
R 31 Recyclization of 7-fluoroalkyl-4,7-dihydroazolo[5,1-c][1,2,4]triazines into 5-(pyrazolinylhydrazono)azoles in the reactions with hydrazides and thiosemicarbazide [Text] / O. G. Khudina, E. V. Shchegol'kov, Ya. V. Burgart, M. I. Kodess, V. I. Saloutin, O. N. Chupakhin // Heterocycles. - 2006. - Vol. 68, № 12. - P2515-2525 Рубрики: ХИМИЧЕСКИЕ НАУКИ |
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 |
A 94 Auto-aromatization of the sigma(H)-adducts of 1,2,4-triazine 4-oxides with carbanions in reactions of nucleophilic substitution of hydrogen [Electronic resource] / D. N. Kozhevnikov, A. M. Prokhorov, V. L. Rusinov, O. N. Chupakhin // Mendeleev Communications. - 2000. - Vol.10, N6. - P227-228 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: 1,2,4-triazine 4-oxides react with stable carbanions to form 5-substituted 1,2,4-triazines as the products of deoxygenation nucleophilic substitution of hydrogen |
A 10 A simple one pot synthesis of condensed 1,2,4-triazines by using the tandem AN-SNipso and SNH-SNipso reactions [Text] / O. N. Chupakhin, G. L. Rusinov, D. G. Beresnev, V. N. Charushin, H. Neunhoeffer // Journal of Heterocyclic Chemistry. - 2001. - Т. 38, № 4. - P901-907 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A new synthetic approach to condensed 1,2,4-triazines based on using the tandem AN-SNipso and SNH-SNipso reactions has been developed. 5-Methoxy-3-penyl-l,2,4 1,2,4-triazine and its N1-methyl quaternary salt were found to react with C,N-, C,O- and N,N?-bifunctional nucleophiles (m-phenylenediamine, resorcinol, semicarbazide and ureas) into triazacarbazoles, benzofuro[2,3-e][1,2,4]-triazines, and 6-azapurine derivatives. In all cases nucleophiles attack first the unsubstituted C-6 carbon of the triazine ring, while the final stage is replacement of the methoxy group affording cyclization products. \\\\Cserver\\dist\\НБО\\Электронная библиотека_Библиогр1\\Journal of Heterocyclic Chemistry\\2001.v.38.p.901.Chupachin.pdf |
R 30 Deoxygenative vs. vicarious nucleophilic substitution of hydrogen in reactions of 1,2,4-triazine 4-oxides with - alpha-halocarbanions [Text] / D. N. Kozhevnikov, V. L. Rusinov, O. N. Chupakhin, M. Makosza, A. Rykowski, E. Wolinska // European Journal of Organic Chemistry. - 2002. - № 8. - P1412-1416 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): AROMATIC SUBSTITUTION -- NUCLEOPHILIC SUBSTITUTION -- NITROGEN HETEROCYCLES Аннотация: The 3,6-diaryl-1,2,4-triazine 4-oxides 1a-e undergo a nucleophilic substitution of hydrogen with the -halomethyl aryl sulfones 2, 3 and 7 by two alternative pathways: vicarious nucleophilic substitution (VNS) and/or an intramolecular deoxygenative process. The former pathway is found to dominate in the reaction of 1 with bromomethyl tolyl sulfone (7) yielding the 5-tosylmethyl-1,2,4-triazine 4-oxides 6, while the reaction with the chloromethyl aryl sulfones 2 and 3 leads to the 5-arylsulfonylchloromethyl-1,2,4-triazines 4 and 5, respectively, as the products of deoxygenative substitution. The reaction of 6-phenyl-1,2,4-triazine 4-oxide (1f) with the chloromethyl aryl sulfones 2 and 3 proceeds differently. At low temperature (-75 C) the products of the VNS reaction at position 5 (6f and 12f) are formed. At room temperature the 7-chloro-1-hydroxy-3-phenyl-7-(arylsulfonyl)-1,4,5-triazahepta-1,3,6-trienes 10f and 11f are obtained by addition of the carbanions 2 and 3 in the 3-position, followed by the ring opening of the resulting adduct. © Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)???????? |
A 10 A versatile strategy for the synthesis of functionalized 2,2 '-bi- and 2,2 ': 6 ',2 '-terpyridines via their 1,2,4-triazine analogues [Text] / V. N. Kozhevnikov, D. N. Kozhevnikov, T. V. Nikitina, V. L. Rusinov, O. N. Chupakhin, M. Zabel, B. Konig // Journal of Organic Chemistry. - 2003. - Vol. 68, № 7. - P2882-2888 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): ALDEHYDES -- OXIDATION -- SUBSTITUTION REACTIONS Аннотация: A general synthetic route for the synthesis of functionalized bi- and terpyridines is reported. Functionalized 1,2,4-triazene 4-oxides 7 and 8 - obtained from the reaction of hydrazones 1 with pyridine aldehydes and followed by oxidation - are functionalized by introduction of a cyano group via nucleophilic aromatic substitution. The thus-obtained 5-cyano-1,2,4-triazines 9 and 10 undergo facile inverse-electron-demand Diels-Alder reactions with enamines and alkenes to yield functionalized bi- and terpyridines, respectively. The substituent at position 6 of the 1,2,4-triazene 4-oxides must be aromatic or heteroaromatic in order to allow their facile synthesis, but other substituents and reagents may vary. Each step of the synthetic route allows diversification, which makes the approach particularly useful for the facile synthesis of a large variety of functionalized bi- and terpyridines. \\\\Expert2\\nbo\\Journal of Organic Chemistry\\2003, v.68, N 7, p.2882. Chupakhin.pdf |
P 93 Protolytic equilibrium of the isomeric phenyl-1,2,4-triazines [Electronic resource] / I. V. Khabibulina, A.P. Volovodenko, R. E. Trifonov, G. V. Yashukova, N. N. Mochul`skaya, V. N. Charushin, G. L. Rusinov, D. G. Beresnev, N. A. Itsikson, V. A. Ostrovskii // Chemistry of Heterocyclic Compounds. - 2003. - Vol. 39, № 5. - P616-623 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The protonation constants for the first and second stages (pK BH+, pKBH2+) of a series of 1,2,4-triazines with a phenyl substituent at various positions in the ring were determined in aqueous solution by a spectrophotometric method. The values of the basicity constants characterizing the first protonation of the heterocycles investigated was in the range of acidity of the medium of pH 3.5 to H0 -2, and the second from H0 -7.3 to H0 -8.7. The position of the phenyl substituent proved to have a significant effect on the size of pK BH+. According to the results of ab initio calculations using HF/6-31G** for the heterocycles investigated the 1H+ form is thermodynamically most stable among the monocations, with the exception of 6-phenyl-1,2,4-triazine for which the existence of the monocation in the 1H+ and 2H+ forms are equally probable. In the case of the dications of all the triazines the 2,4-H,H2+ tautomer is the most preferred. The aromaticity of the 1,2,4-triazine ring is changed insignificantly on mono- and diprotonation. \\\\Expert2\\nbo\\Chemistry of Heterocyclic Compounds\\2003, v.39, N 5, p.616. .pdf |