S 59 Sigma-adducts of 1,2,4-triazine 4-oxides with Nucleophiles. II.Oxidation and Elimination as Two Pathways of sigma-adducts Aromatization [Text] : доклад, тезисы доклада / O. N. Chupakhin, I. S. Kovalev, D. N. Kozhevnikov, V. L. Rusinov // International Memorial I.Postovsky Conference on Organic Chemisty, Ekaterinburg, March 17-20, 1998 : program and abstracts. - Ekaterinburg, 1998. - P80 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 |
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 and antiviral activity of 2-amino-3-ethoxycarbonylpyrazine derivatives [Electronic resource] / V. L. Rusinov [et al.] // Pharmaceutical Chemistry Journal. - 2005. - Vol. 39, № 12. - P630-635. - Библиогр. : с. 635 (6 назв.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A series of substituted 2-amino-3-ethoxycarbonylpyrazines containing indole, resorcinol, thiophenol, ethyl cyanoacetate, indandione, and antipyrine moieties was obtained via reactions of nucleophilic substitution of hydrogen in the initial 2-aminopyrazine-1-oxides. Some of the synthesized compounds inhibit the reproduction of measles viruses and exhibit a weak antiviral activity with respect to Marburg virus. However, most of the new substituted pyrazines are not cytotoxic and exhibit no activity against ortho-poxviruses and measles viruses. \\\\Expert2\\nbo\\Pharmaceutical Chemistry Journal\\2005, 39 (12), 630.pdf |
D 62 Direct introduction of indoles into 2-aminopyrazine 1-oxides [Electronic resource] / I. S. Kovalev, D. N. Kozhevnikov, V. L. Rusinov, O. N. Chupakhin, D. V. Raikov, V. A. Pustovarov, B. V. Shul'gin // Mendeleev Communications. - 2000. - Vol.10, N6. - P229-230 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The synthesis of indolyl derivatives of 2-aminopyrazine, analogues of the bioluminescent natural product Cypridina etioluciferamine, with enhanced photoluminescent properties, is reported. |
S 81 Stable sigma(H)-adducts in reactions of ferrocenyllithium with azines [Electronic resource] / I. A. Utepova, A. E. Lakhina, M. V. Varaksin, I. S. Kovalev, V. L. Rusinov, P. A. Slepukhin, M. I. Kodess, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2008. - Vol. 57, № 10. - P2156-2161 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Stable sigma(H)-adducts as intermediates of the nucleophilic substitution of hydrogen in 3-(2-pyridyl)-1,2,4-triazines were obtained for the first time using ferrocenyllithium as a nucleophilic reagent. The three-dimensional structures of the reaction products were established based on the X-ray diffraction study of 1-[4-ethyl-6-phenyl-3-(2-pyridyl)-5(H)-1,2,4-triazin-5-yl]f \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2008, 57 (10), 2156.pdf |
T 82 Transformations of 1,2,4-Triazines in Reactions with Nucleophiles: V. SNH and ipso-Substitution in the Synthesis and Transformations of 5-Cyano-1,2,4-triazines [Electronic resource] / D. N. Kozhevnikov, V. N. Kozhevnikov, I. S. Kovalev, V. L. Rusinov, O. N. Chupakhin, G. G. Aleksandrov // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2002. - Vol. 38, № 5. - P744-750 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The scope of functionalization of 1,2,4-triazines can be considerably extended via successive nucleophilic substitution of hydrogen (SN H) and ipso-substitution. A convenient procedure has been developed for direct cyanation of 1,2,4-triazine 4-oxides with acetone cyanohydrin in the presence of triethylamine. The cyano group in the resulting 5-cyano-1,2,4-triazines is readily replaced by reactions with various aliphatic alcohols and amines \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2002, 38 (5), 744.pdf |
S 10 S-N(H) reactions of pyrazine N-oxides and 1,2,4-triazine 4-oxides with CH-active compounds [Electronic resource] / D. N. Kozhevnikov, I. S. Kovalev, A. M. Prokhorov, V. L. Rusinov, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2003. - Vol. 52, № 7. - P1588-1594 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Nucleophilic substitution of hydrogen in pyrazine N-oxides under the action of CH-active compounds requires activation with acylating agents. This activation facilitates aromatization of intermediate H adducts via elimination of the acid residue to form substituted pyrazines. More electrophilic 1,2,4-triazine 4-oxides react with carbanions derived from CH-active compounds without additional activation according to a scheme, which has previously been unknown for azine N-oxides. This scheme involves aromatization of H adducts through elimination of water by the E1cb mechanism. The reaction products occur in DMSO-d6 solutions predominantly as 6-methylene-1,6-dihydropyrazines and 5-methylene-4,5-dihydro-1,2,4-triazines.??nucleophilic substitution of hydrogen - 1,2,4-triazine 4-oxide - pyrazine 1-oxide - carbanion - CH-active compounds?? \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2003, 52 (7), 1588.pdf |
S 10 S-N(H) reactions of 1,2,4-triazine N-oxides, pyrazine N-oxides, and pterin N-oxides with arenethiols [Electronic resource] / D. N. Kozhevnikov, I. S. Kovalev, V. L. Rusinov, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2001. - Vol. 50, № 6. - P1068-1071 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: 1,2,4-Triazine 4-oxides were found to enter into the reactions of nucleophilic substitution of hydrogen with S-nucleophiles (arenethiols) in the presence of acylating agents and trifluoroacetic acid. The reactions proceeded with loss of the N-oxide function to form 5-arylthio-1,2,4-triazines. 2-Amino-3-ethoxycarbonylpyrazine 1-oxides and 2-amino-4-oxopterin 8-oxides react with arenethiol analogously \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2001, 50 (6), 1068.pdf |
S 10 S- N(H) Reaction of lithiated nitronyl nitroxide with quinoline N-oxide [Electronic resource] / V. Ovcharenko, O. N. Chupakhin, I. S. Kovalev, E. V. Tretyakov, G. V. Romanenko // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2008. - Vol. 57, № 10. - P2227-2229 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The SNH reaction of lithiated 4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazole-1-oxyl 3-oxide with quinoline N-oxide affords 4,4,5,5-tetramethyl-2-(1-oxidoquinolin-2-yl)-4,5-dihydro-1H-imidazole-1-oxyl 3-oxide \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2008, 57 (10), 2227-2229.pdf |
K 79 Kovalev, I. S. Reaction of 2-pyridyllithium with azine N-oxides. Simple and convenient method for the synthesis of 2,2-bipyridine 1-oxide and 2,2:6,2:62-tetrapyridine 1-oxide [Electronic resource] / I. S. Kovalev, V. L. Rusinov, O. N. Chupakhin // Chemistry of Heterocyclic Compounds. - 2009. - Vol. 45, № 2. - P176-181 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: In the reaction of 2-pyridyllithium with quinoline 1-oxide and isoquinoline 2-oxide a nucleophilic substitution of hydrogen occurs to form the corresponding pyridin-2-ylquinolines. A dimerization of the substrate occurs with pyridine 1-oxide, 2,2-bipyridine 1-oxide or quinoxaline N-oxide. A similar dimerization in good yield occurs when treating azine N-oxides with tert-butyllithium and this serves as a simple and convenient method for preparing bi- and tetrapyridines \\\\Expert2\\nbo\\Chemistry of Heterocyclic Compounds\\2009, v.45, N 2, p.176.pdf |
T 82 Transformations of 1,2,4-triazines in reactions with nucleophiles: IV. Nucleophilic substitution of hydrogen in 1,2,4-triazine 4-oxides under acylation conditions [Text] / V. L. Rusinov, D. N. Kozhevnikov, I. S. Kovalev, O. N. Chupakhin, G. G. Aleksandrov // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2000. - Vol. 36, № 7. - P1050-1060. - Bibliogr. : p. 1060 (13 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): 3-SUBSTITUTED 6-PHENYL-1,2,4-TRIAZINE 4-OXIDES -- AROMATIC NUCLEOPHILES -- AUTOAROMATIZATION -- KINETIC REGIOSELECTIVITY -- THERMODYNAMIC REGIOSELECTIVITY |
T 44 The C-C coupling of ferrocenes with electron-deficlent azaaromatics - a new route for construction of heterocyclic ligands and complexes [] / O. N. Chupakhin, I. S. Kovalev, I. A. Utepova, V. L. Rusinov, V. N. Charushin // 20-th International Congress of Heterocyclic Chemistry, Palermo, July 31-August 5, 2005 : book of abstracts . - Palermo, Italy, 2005. - С. 507. - Библиогр.: с. 507 (3 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ |
D 62 Direct introduction of ferrocene moiety into azaheterocycles [Text] / O. N. Chupakhin, I. S. Kovalev, I. A. Utepova, V. L. Rusinov // 14th European Symposium on Organic Chemistry, Helsinki, Finland, 4-8 July 2005 : abstracts . - Helsinki, Finland, 2005. - P293. - Bibliogr. : p. 293 (2 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ |
R 30 Reactions of quinoxaline with 3-methyl-1-phenylpyrazol-5-one / Y. A. Azev, E. D. Oparinaa, I. S. Kovalev, P. A. Slepukhin, R. K. Novikova // Mendeleev Communications. - 2012. - Vol.22, №1. - С. 37-38 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): QUINOXALINES -- PHENYLPYRAZOL -- TRIETHYLAMINE Аннотация: Quinoxaline during the reaction with 3-methyl-1-phenylpyrazol-5-one in the presence of triethylamine at room temperature in dimethylsulfoxide eliminates o-phenylenediamine and gives 4,4’-methylene-bis(3-methyl-1-phenylpyrazol-5-one) and 1,1,2,2-tetrakis(5-methyl-2-oxo-2-phenyl-1,2-dihydro-3H-pyrazol-4-yl)ethane. The latter was proved to be the intermediate to form the above dipyrazolylmethane derivative \\\\Expert2\\nbo\\Mendeleev Communications\\2012, v.22, p. 37.pdf |
A 81 Aryne intermediates in the synthesis of polynuclear heterocyclic systems (Review) / I. S. Kovalev, D. S. Kopchuk, G. V. Zyryanov, P. A. Slepukhin, V. L. Rusinov, O. N. Chupakhin // Chemistry of Heterocyclic Compounds. - 2012. - Vol.48, №4. - С. 536-547 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): ARYNE INTERMEDIATES -- DIENOPHILES -- DIELS-ALDER REACTIONS Аннотация: Published examples of the polynuclear fused heterocyclic systems production by cycloaddition reactions involving aryne intermediates generated in situ are reviewed \\\\Expert2\\nbo\\Chemistry of Heterocyclic Compounds\\2012, v.48, N 4, p.536-547.pdf |
C 52 Chichibabin-Type Condensation of Cyclic Ketones with 3-R-1,2,4-triazin-5(4H)-ones / I. N. Egorov, T. A. Tseitler, I. S. Kovalev, P. A. Slepukhin, V. L. Rusinov, O. N. Chupakhin // Journal of Organic Chemistry. - 2012. - Vol.77, №14. - С. 6007-6013 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): CYCLIC KETONES -- TRIAZINE -- KETONES Аннотация: Reactions between substituted 1,2,4-triazines and ketones were investigated. General procedures for one-pot synthesis of hydrogenated derivatives of such polycyclic systems as benzo[c][1,2,4]triazino[1,6-a][2]azecine, [1,2,4]triazino[1,6-f]phenantridine, and dicyclopenta[b,d]pyrido[1,2-f][1,2,4]triazine are described \\\\Expert2\\nbo\\Journal of Organic Chemistry\\2010, v.77, p.6007.pdf |
P 91 Preparation of (benzo)isoquinolines using in situ generated aryne intermediates [Electronic resource] / D. S. Kopchuk, G. V. Zyryanov, I. S. Kovalev, V. L. Rusinov, I. N. Egorov, O. N. Chupakhin // Chemistry of Heterocyclic Compounds. - 2013. - Vol.48, №12. - P1871-1873 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): (BENZO)ISOQUINOLINE -- 1,2,4-TRIAZINE -- ARYNE INTERMEDIATES -- CYCLOADDITION -- DIELS-ALDER REACTION \\\\expert2\\NBO\\Chemistry of Heterocyclic Compounds\\2013, v.48, N 12, p. 1871-1873.pdf |
P 91 Preparation of Pyridyl-substituted Monoazatriphenylenes [Electronic resource] / D. S. Kopchuk, G. V. Zyryanov, I. S. Kovalev, A. F. Khasanov, A. S. Medvedevskih, V. L. Rusinov, O. N. Chupakhin // Chemistry of Heterocyclic Compounds. - 2013. - Vol.49, №3. - P500-502. - Библиогр.: с. 502 (18 ref/) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): MONOAZATRIPHENYLENES -- PYRIDYL \\\\expert2\\NBO\\Chemistry of Heterocyclic Compounds\\2013, v.49, N 3, p. 500-502.pdf |
P 91 Preparation of triazatriphenylene cations, promising chemosensors for nitro compounds [Electronic resource] / D. S. Kopchuk, I. N. Egorov, T. A. Tseitler, A. F. Khasanov, I. S. Kovalev, G. V. Zyryanov, V. L. Rusinov, O. N. Chupakhin // Chemistry of Heterocyclic Compounds. - 2013. - Vol.49, №3. - P503-505. - Библиогр.: с. 505 (10 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): TRIAZATRIPHENYLENE -- CATIONS -- NITRO COMPOUNDS \\\\expert2\\NBO\\Chemistry of Heterocyclic Compounds\\2013, v.49, N 3, p. 503-505.pdf |