П 71 Превращения 8-замещенных тетразоло[1,5-a]пиразинов [] = Transformations of 8-substituted tetrazolo[1,5-a]pyrazines / П. А. Слепухин, Г. Л. Русинов, С. С. Деденева, В. Н. Чарушин // Изв. АН. Сер. Химическая. - 2007. - № 2. - С. 334-338 : рис., табл. - Библиогр. : с. 338 (12 назв.) . - ISSN 0002-3353 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 |
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 |
T 82 Transformations of 8-substituted tetrazolo[1,5-a]pyrazines [Electronic resource] / P. A. Slepukhin, G. L. Rusinov, S. Dedeneva, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2007. - Vol. 56, № 2. - P345-350 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The reactions of 8-chlorotetrazolo[1,5-a]pyrazine with N-, O-, and S-nucleophiles involve the ipso substitution of the chlorine atom. Heating of this compound with benzotriazole or phenyltetrazole results in elimination of the nitrogen molecule from one of the tetrazole rings to form new annelated azapentalenes \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2007, 56 (2), 345.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 |
R 30 Reactions of sigma(H)-adducts of 1-ethyl-1,4-diazinium salts with arylalkynes as a one-step approach to pyrrolo[1,2-a]pyrazine derivatives [Electronic resource] / E. V. Verbitskiy, P. A. Slepukhin, M. A. Ezhikova, M. I. Kodess, G. L. Rusinov, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2009. - Vol. 58, № 6. - P1291-1293 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The O- and C-adducts of 5-aryl and 5-hetaryl-2,3-dicyano-1-ethylpyrazinium salts are hidden sources of ylides, which can be used for the cyclization with arylacetylenes giving rise to pyrrolo[1,2-a]pyrazines \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2009, 58 (6), 1291-1293.pdf |
R 30 Reactions of radicals generated from 1-ethyl-1,4-diazinium salts: addition to the C-C triple bond 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 : an International Journal for Reviews and communications in Heterocyclic Chemistry. - 2011. - V. 78, № 9. - P2315-2324 : граф., табл. - Библиогр.: с. 2323-2324 (32 назв.) 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 pyraziny! radicals can also be involved into the addition reaction on the C-C tziple 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. |
D 62 Direct C—C-coupling of ferrocenyl- and cymantrenyllithium [Electronic resource] / I. A. Utepova, A. A Musikhina, Yu. A. Kvashnin, M. A. Shcherbakova, P. O. Serebrennikova, G. L. Rusinov, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2011. - Vol.60, №12. - С. 2531-2535. - Bibliogr. : p. 2535 (15 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): FERROCENYLLITHIUM -- CYMANTRENYLLITHIUM -- HYDROGEN Аннотация: A direct C—C coupling of ferrocenyl and cymantrenyllithium with 5 (het)aryl 1,2,5 oxadiazolo[3,4 b]pyrazines was accomplished. Main characteristics of the SN H reaction prod ucts were obtained, as well as crystallographic data on the spatial structure of oxadiazolopyr azinylferrocenes and cymantrenes synthesized \\\\expert2\\NBO\\Russian Chemical Bulletin\\2011, 60 (12), 2531-2535.pdf |
D 62 Direct arylalkenylation of furazano[3,4-b]pyrazines via a new C-H functionalization protocol [Electronic resource] / N. A. Kazin, Yu. A. Kvashnin, R. A. Irgashev, W. Dehaen, G. L. Rusinov, V. N. Charushin // Tetrahedron Letters. - 2015. - Vol. 56, № 14. - С. 1865-1869. - Bibliogr. : p. 1869 (20 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): NUCLEOPHILIC-SUBSTITUTION -- DERIVATIVES -- HYDROGEN Аннотация: 6-Styryl-5-(het)arylfurazano[3,4-b]pyrazines have been obtained by novel C-H functionalization, which is a particular case of the nucleophilic substitution of hydrogen (S-N(H)). The process is initiated by the Michael addition of morpholine at the C=C double bond of beta-nitrostyrenes, and the subsequent addition of the generated carbanion to C-6 of 5-(het)arylfurazano[3,4-b]pyrazines, followed by elimination of nitrous acid and morpholine. It has been shown that in this case, only beta-nitrostyrenes bearing electron-rich substituents on the aromatic ring are involved in arylalkenylation of furazano[3,4-b]pyrazines \\\\expert2\\nbo\\Tetrahedron Letters\\2015, v. 56, p. 1865.pdf |
S 98 Synthesis, antimycobacterial and antifungal evaluation of some new 1-ethyl-5-(hetero)aryl-6-styryl-1,6-dihydropyrazine-2,3-dicarbonitriles [Electronic resource] / E. V. Verbitskiy, P. A. Slepukhin, M. A. Kravchenko, S. N. Skornyakov, N. P. Evstigneeva, N. V. Kungurov, N. V. Zil'berberg, G. L. Rusinov, O. N. Chupakhin, V. N. Charushin // Bioorganic and Medicinal Chemistry Letters. - 2015. - Vol. 25, № 3. - С. 524-528. - Bibliogr. : p. 528 (16 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): PYRAZINES -- ANTITUBERCULOSIS ACTIVITY -- PETASIS REACTION Аннотация: The Petasis reaction of 6-hydroxy adducts of 1-alkyl-2,3-dicyano-5-arylpyrazinium salts with trans-styrylboronic acids proved to proceed smoothly at room temperature to give the corresponding 5-(hetero)aryl-6-styryl substituted 1,6-dihydropyrazine derivatives. Also it has been found that C(6) unsubstituted 1,6-dihydro- or 1,4,5,6-tetrahydropyrazine derivatives can be easy prepared in high yields from the corresponding pyrazinium salts by reduction with triethylsilane. All synthesized compounds were screened in vitro for their antifungal activities against seven pathogenic fungal strains and antimycobacterial activities against Mycobacterium tuberculosis H(37)Rv, avium, terrae and multi-drug-resistant strains isolated from tuberculosis patients in the Ural region (Russia) \\\\expert2\\nbo\\Bioorganic and Medicinal Chemistry Letters\\2015, v. 25, p. 524.pdf |
A 10 A facile, metal-free, oxidative coupling of new 6-(hetero)aryl-[1,2,5]oxadiazolo[3,4-b]pyrazines with pyrroles, indoles and carbazoles. / Yu. A. Kvashnin, N. A. Kazin, E. V. Verbitskiy, T. S. Svalova, A. V. Ivanova, A. Kozitsina, P. A. Slepukhin, G. L. Rusinov, O. N. Chupakhin, V. N. Charushin // ARKIVOC. - 2016. - Vol. V. - С. 279-300. - Bibliogr. : p. 297-300 (45 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): PYRAZINES -- PYRROLES -- INDOLES \\\\expert2\\NBO\\ARKIVOC\\2016, p.279-300.pdf |
S 98 Synthesis and Antitubercular Evaluation on Novel 1-Ethyl-5-(hetero)aryl- 1,6-dihydropyrazine-2,3-dicarbonitriles and 3-Cyano-1-ethyl-5-(hetero) aryl-2(1H)-pyrazinones / M. A. Kravchenko, E. V. Verbitskiy, S. N. Skornyakov, P. A. Slepukhin, G. L. Rusinov, O. N. Chupakhin, V. N. Charushin // Anti-Infective Agents. - 2016. - Vol. 14, № 2. - С. 139-144 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): PYRAZINES -- ANTITUBERCULOSIS ACTIVITY -- 2(1H)-PYRAZINONE Аннотация: A simple method based on hydrolysis of 2,3-dicyanopyrazinium salts has been used for the synthesis of the corresponding 5-(hetero)aryl-3-cyano-1-ethyl-2(1H)-pyrazinones. Also, the series of novel 1-ethyl-5-(hetero)aryl-1,6-dihydropyrazine-2,3-dicarbonitriles have been obtained through reduction of the same pyrazinium salts with triethylsilane. The obtained compounds proved to be active in micromolar concentrations in vitro against Mycobacterium tuberculosis H37Rv, Mycobacterium avium, Mycobacterium terrae, as well as against rifampicin and isoniazid-resistance strains of Mycobacterium tuberculosis. The data for acute in vivo toxicity in mice have been obtained for these compounds which appear to be promising antitubercular agents |