Ч-92 Чупахин, О. Н. Нуклеофильная атака на незамещенный атом углерода азинов и нитроаренов - эффективная методология построения гетероциклических систем [] = Nucleophilic attack on the unsubstituted carbon atoms of azines and nitroarenes as an efficient strategy for constructing heterocyclic systems : обзор / О. Н. Чупахин, Д. Г. Береснев // Успехи химии. - 2002. - Т. 71, N 9. - 803-818: схем. - Библиогр. : с. 817-818 (69 назв.) . - ISSN 0042-1308 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Обобщены данные о новых методах синтеза конденсированных азинов с помощью нуклеофильной атаки на незамещенный атом углерода азинов и нитроаренов. Рассмотрены тандемы реакций нуклеофильного присоединения AN-AN, нуклеофильного присоединения-замещения AN-S(ipso)N, нуклеофильного замещения S(H)N-S(ipso)N и S(H)N-S(H)N, протекающих между азинами и бинуклеофилами; внутримолекулярные S(H)N-реакции в ряду азинов и нитроаренов, а также другие методы синтеза конденсированных гетероциклов, основанные на процессах нуклеофильного замещения типа S(H)N |
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 70 Fluorine-containing heterocycles. XV. Reactions of polyfluorobenzoyl isothiocyanates with amino azines and amino azoles [Electronic resource] / E. V. Nosova, G. N. Lipunova, A. A. Laeva, V. N. Charushin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2006. - Vol. 42, № 10. - P1544-1550. - Библиогр. : с. 1550 (9 назв.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Reactions of tetra-and pentafluorobenzoyl isothiocyanates with aminoazoles and aminoazines led to the formation of fluorinated 1,3-benzothiazin-4-ones which reacted with cyclic amines in different ways. Replacement of the N=C=S fragment was observed in some reactions of polyfluorobenzoyl isothiocyanates with nucleophiles. \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2006, 42 (10), 1544.pdf |
A 89 Asymmetric induction in the nucleophilic addition in the series of aromatic azines [Electronic resource] / I. N. Egorov, G. V. Zyryanov, V. L. Rusinov, O. N. Chupakhin // Russian Chemical Reviews. - 2005. - Vol. 74, № 12. - P1073-1087 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Stereoselective reactions of nucleophilic addition to the C=N bond in aromatic azines resulting in chiral products are reviewed. Various methods of inducing the optical activity are discussed. \\\\Expert2\\nbo\\Russian Chemical Reviews\\2005, V.74, p.1073.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 |
P 93 Prokhorov, A. M. Direct introduction of acetylene moieties into azines by S(N)H methodology [Text] / A. M. Prokhorov, M. Makosza, O. N. Chupakhin // Tetrahedron Letters. - 2009. - Vol. 50, № 13. - P1444-1446 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The N-oxides of azines 1a–g react with lithium and/or potassium acetylides to give the corresponding ethynylazines 2a–g. Reaction with lithium acetylide requires subsequent acylation of the intermediate anionic adduct for rearomatization whereas in the case of potassium acetylide, auto-aromatization takes place?? \\\\Expert2\\nbo\\Tetrahedron Letters\\2009, V. 50, N 13, p.1444.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 |
А 90 Асимметрическая индукция в реакциях нуклеофильного присоединения в ряду ароматических азинов [] = Asymmetric induction in the nucleophilic addition in the series of aromatic azines / И. Н. Егоров, Г. В. Зырянов, В. Л. Русинов, О. Н. Чупахин // Успехи химии. - 2005. - Т. 74, № 12. - С. 1176-1192. - Библиогр.: с. 1192 (60 назв.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): АСИММЕТРИЧЕСКАЯ ИНДУКЦИЯ -- ОПТИЧЕСКАЯ АКТИВНОСТЬ -- АРОМАТИЧЕСКИЕ АЗИНЫ Аннотация: Представлены стереоселективные реакции нуклеофильного присоединения по связи C=N ароматических азинов, приводящие к хиральным продуктам. Рассмотрены различные пути наведения оптической активности |
N 52 New method for the annelation of the pyridine fragment to azines [Electronic resource] / V. N. Charushin, A. M. Boguslavskii, M. G. Ponizovskii, M. I. Kodess, A. N. Chekhlov, Sh. G. Mkoyan, S. M. Aldoshin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2004. - Vol. 53, № 6. - P1267-1271 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The reaction of quinoxaline-2-carbaldehyde with ethyl (E)-3-aminocrotonate afforded ethyl 4-oxo-1,4-dihydropyrido[2,3-b]quinoxaline-3-carboxylate, which is a structural analog of nalidixic and 4-quinolone-3-carboxylic acids representing the basis of the known antibacterial drugs of the fluoroquinolone series \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2004, 53 (6), 1267.pdf |
S 73 Sosnovskikh, V. Ya. Reaction of 3,3-dialkyl-6-trifluoromethyl-2,3-dihydro-4-pyrones with hydrazine hydrate [Electronic resource] / V. Ya. Sosnovskikh, M. Yu. Mel'nikov, M. I. Kodess // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 1998. - Vol. 47, № 7. - P1365-1368 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: 3,3-Dialkyl-2,3-dihydro-6-trifluoromethyl-4-pyrones react with hydrazine hydrate to give 2-hydrazino-2-trifluoromethyl-4-tetrahydropyrone hydrazones. When heated, the latter are transformed into 3(5)-(2-hydroxyethyl)-5(3)-trifluoromethylpyrazoles, while their treatment with HCl in ether leads to 3,3-dialkyl-2,3-dihydro-6-trifluoromethyl-4-pyrone azines \\\\Expert2\\nbo\\Russian Chemical Bulletin\\1998, 47 (7), 1365.pdf |
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 |
F 70 Fluorinated azines and benzazines containing oxygen or sulfur atoms [Text] / E. V. Nosova, G. N. Lipunova, V. N. Charushin, O. N. Chupakhin // Journal of Fluorine Chemistry. - 2010. - Vol. 131, № 12. - P1267-1288 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: In the frames of this review article the recently obtained data on synthetic approaches to fluorinated oxa(thia)azines and benzazines, their chemical properties, structure, and biological activity have been analyzed \\\\Expert2\\nbo\\Journal of Fluorine Chemistry\\2010, v. 131, p.1267.pdf |
C 57 Chupakhin, O. N. Nucleophilic attack on the unsubstituted carbon atom of azines and nitroarenes as an efficient methodology for constructing heterocyclic systems [Electronic resource] / O. N. Chupakhin, D. G. Beresnev // Russian Chemical Reviews. - 2002. - Vol. 71, № 9. - P707-720. - Bibliogr. : p. 720 (69 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Data on new methods for the synthesis of fused azines by nucleophilic attack on the unsubstituted carbon atom of azines and nitroarenes are generalised. The review surveys tandem reactions of azines with binucleophiles comprising nucleophilic addition AN–AN nucleophilic addition–substitution AN–SipsoN, and nucleophilic substitutions SHN–SipsoN and SHN-SHN. Intramolecular SHN reactions of azines and nitroarenes and other methods for the synthesis of fused heterocycles based on SHN nucleophilic substitution are also discussed |
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 |
S 98 Synthesis of chiral ferrocenylazines. Negishi cross-coupling or S N H reactions? [Electronic resource] / A. A Musikhina, I. A. Utepova, N. S. Serebryakov, O. N. Chupakhin, V. N. Charushin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2013. - Vol.49, №8. - С. 1191-1194. - Bibliogr. : p. 1194 (28 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): SYNTHESIS -- CHIRAL FERROCENYLAZINES -- NEGISHI Аннотация: Preparation of new hetaryl-containing planar chiral ferrocene by a nucleophilic substitution of hydrogen in azines was performed using a lithium derivative of (S)-ferrocenyl-p-tolylsulfoxide as s nucleophilic reagent \\\\expert2\\NBO\\Russian Journal of Organic Chemistry\\2013, 49, (8), 1191-1194.pdf |
A 89 Asymmetric Reactions of a Series of Aromatic Azines with Nucleophiles / I. N. Egorov, T. A. Tseitler, G. V. Zyryanov, V. L. Rusinov, O. N. Chupakhin // Heterocycles. - 2012. - Vol.86, №2. - С. 821-889 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): NUCLEOPHILIC ADDITION -- AZINE SERIES -- STEREOSELECTIVE FORMATION Аннотация: Current review is devoted to the reactions of nucleophilic addition in azine series, leading to the stereoselective formation of optically active products. Three types of reactions are reviewed: the reactions of achiral nucleophiles with chiral azines; the reactions of chiral nucleophiles with achiral azines; reactions of achiral nucleophiles with achiral azines in the presence of chiral catalysts |
S 98 Synthesis of new meso-substituted heterocyclic calix[4]arenes via SN H approach [Electronic resource] / M. V. Varaksin, I. A. Utepova, G. N. Chupakhin, V. N. Charushin // Macroheterocycles . - 2013. - Vol.6, №4. - С. 308-314. - Bibliogr. : p. 313-314 (42 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): AZINES -- C-C COUPLING -- CALIX[4]ARENES Аннотация: An effective synthetic approach to heterocyclic derivatives of meso-substituted calixarenes has been suggested by using the SN H methodology based on the direct, non-catalyzed by transition metals, C-C coupling of 1,2,4-triazines with the lithium salts of tetramethoxycalix[4]arenes |
D 62 Direct Nucleophilic Functionaliation of Arines and their N-Oxidesby Lithiumaldonitrones / S. V. Mikhaylov, M. V. Varaksin, I. A. Utepova, O. N. Chupakhin, V. N. Charushin // Уральский научный форум "Современные проблемы органической химии". XVII Молодежная школа-конф. по органической химии, Екатернинбург, 8-12 июня 2014 г. : сб. тез. - Екатеринбург, 2014. - С. 238. - Bibliogr. : p. 238 (3 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): AZINES -- LITHIUMALDONITRONES -- HETEROCYCLIC COMPOUNDS |
T 98 Two Approaches in the Synthesis of Planar Chiral Azinylferrocenes [Electronic resource] / I. A. Utepova, O. N. Chupakhin, P. O. Serebrennikova, A. A Musikhina, V. N. Charushin // Journal of Organic Chemistry. - 2014. - Vol. 79, № 18. - С. 8659-8667. - Bibliogr. : p. 8666-8667 (34 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): CHIRAL AZINYLFERROCENES -- CROSS-COUPLING REACTION -- HALOGENATED AZINES Аннотация: Two synthetic routes to the chiral azinylferrocenes (CAFs) 5 and 15, key intermediates for the synthesis of new enantiomerically enriched P,N-ligands, have been compared. The first approach is based on the palladium-catalyzed cross-coupling reaction of halogenated azines with organozinc derivatives of ferrocenes (the Negishi reaction). The second approach exploits a new synthetic methodology, which provides a shorter pathway, through the direct C–H functionalization of aromatics by the C–C coupling of halogen-free (hetero)arenes with lithium ferrocenes bearing stereogenic C and S atoms. The palladium complexes of P,N-ligands have been used as catalysts for the Tsuji–Trost reaction, which proceeds with high enantioselectivity to give allylic substitution products in good yields. \\\\expert2\\nbo\\Journal of Organic Chemistry\\2014, v.79, p.8659.pdf |
D 62 Direct nuclophilic C-H functionalization of azines and their N-oxides by lithium derivatives of aldonitrones [Electronic resource] / M. V. Varaksin, I. A. Utepova, O. N. Chupakhin, V. N. Charushin // Tetrahedron. - 2015. - Vol. 71, №38. - С. 7077-7082. - Bibliogr. : p. 7082 (23 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): DIPOLE-STABILIZED CARBANIONS -- ORGANIC-SYNTHESIS -- CHEMICAL-PROPERTIES; Аннотация: Novel ligands of the azine family for complexing with metals have been obtained as a result of the uncatalyzed C-C coupling reactions of quinoline, quinoxaline, 1,10-phenantroline, and their N-oxides with (1-oxido-3-phenyl-1,4-diazaspiro[4.5]deca-1,3-dien-2-yl)lithium \\\\expert2\\nbo\\Tetrahedron\\2015, v. 71 , p. 7077-7082.pdf |