C 75 Consecutive S-N(H) and Suzuki–Miyaura Cross-Coupling Reactions – an Efficient Synthetic Strategy to Pyrimidines Bearing Pyrrole and Indole Fragments / E. V. Verbitskiy, G. L. Rusinov, V. N. Charushin, O. N. Chupakhin, E. M. Cheprakova, P. A. Slepukhin, M. G. Pervova, M. I. Kodess // European Journal of Organic Chemistry. - 2012. - Vol. 2012, №33. - С. 6612-6621 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): SYNTHETIC METHODS -- CROSS-COUPLING -- NITROGEN HETEROCYCLES Аннотация: The combination of the Suzuki–Miyaura cross-coupling and nucleophilic aromatic substitution of hydrogen reactions is a versatile tool for the syntheses of 4-(1R-pyrrol-2-yl)- and 4-(1R-indol-3-yl)-5-(hetero)aryl-substituted pyrimidines from commercially available 5-bromopyrimidine. The SNH [AE, (addition–elimination)] and SNH [AO, (addition–oxidation)] reactions of 5-bromopyrimidine with pyrroles and indoles were studied by gas chromatography–mass spectrometry. The structures of the intermediate σH adducts as well as the pyrrole-(hetero)arylpyrimidine and indole-(hetero)arylpyrimidine dyads were established for the first time by X-ray crystal structure analysis \\\\Expert2\\nbo\\European Journal of Organic Chemistry\\2012, p.6612.pdf |
P 17 Palladium(II)-Catalyzed Oxidative C–H/C–H Coupling and Eliminative SNH Reactions in Direct Functionalization of Imidazole Oxides with Indoles / M. V. Varaksin, I. A. Utepova, O. N. Chupakhin, V. N. Charushin // Journal of Organic Chemistry. - 2012. - Vol.77, №20. - С. 9087-9093 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): IMIDAZOLE OXIDES -- INDOLES Аннотация: Two novel synthetic approaches to realize the direct C(sp2)–H bond functionalization in cyclic nitrones are reported. Palladium(II)-catalyzed oxidative C–C coupling of 2,2-dialkyl-4-phenyl-2H-imidazole 1-oxides with indoles was shown to result in the formation of 5-indolyl-3-yl derivatives, while nucleophilic substitution of hydrogen (SNH) at C(5) of the same imidazole system was found to afford the corresponding deoxygenated compounds \\\\Expert2\\nbo\\Journal of Organic Chemistry\\2010, v.77, p.9087.pdf |
R 30 Reactions of azinium cations. 6. N(1)-alkyl-1,2,4-triazinium salts. Reactions with indoles — The first case of the double addition of nucleophiles to a triazine ring [Electronic resource] / S. G. Alekseev, V. N. Charushin, O. N. Chupakhin, S. V. Shorshnev, A. I. Chernyshev, N. A. Klyuev // Chemistry of Heterocyclic Compounds. - 1986. - Vol. 22, № 11. - С. 1242-1249. - Bibliogr. : p. 1249 (31 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): 1,4-DIAZINIUM SALTS -- INDOLES -- AZINIUM CATIONS Аннотация: N(1)-Alkyl-3-morpholino-1,2,4-triazinium salts and N(1)-alkyl-3-pyrrolidino-1,2,4-triazinium salts were synthesized. The structures of these salts were established by 13C NMR spectroscopy. 1,2,4-Triazinium cations add indoles at C(5) and C(6) thereby displaying properties characteristic for 1,4-diazinium salts. \\\\expert2\\nbo\\Chemistry of Heterocyclic Compounds\\1986, v.22, N 11, p. 1242.pdf |
A 10 A new and convenient synthetic way to 2-substituted thieno[2,3-b]indoles [Electronic resource] / R. A. Irgashev, A. A. Karmatsky, G. L. Rusinov, V. N. Charushin // Beilstein Journal of Organic Chemistry. - 2015. - Vol. 11. - С. 1000-1007. - Bibliogr. : p. 1006-1007 (35 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): ALDOL-CROTONIC CONDENSATION -- LAWESSON'S REAGENT -- ISATIN Аннотация: A short and robust approach for the synthesis of 2-(hetero)aryl substituted thieno[2,3-b]indoles from easily available 1-alkylisatins and acetylated (hetero)arenes has been advanced. The two-step procedure includes the "aldol-crotonic" type of condensation of the starting materials, followed by treatment of the intermediate 3-(2-oxo-2-(hetero)arylethylidene) indolin-2-ones with Lawesson's reagent. The latter process involves two sequential reactions, namely reduction of the C=C ethylidene double bond of the intermediate indolin-2-ones followed by the Paal-Knorr cyclization, thus affording tricyclic thieno[2,3-b]indoles. \\\\expert2\\nbo\\Beilstein Journal of Organic Chemistry\\2015, v. 11, p.1000-1007.pdf |
A 23 Aerobic oxidative C-H/C-H coupling of azaaromatics with indoles and pyrroles in the presence of TiO2 as a photocatalyst [Electronic resource] / I. A. Utepova, M. A. Trestsova, O. N. Chupakhin, V. N. Charushin, A. A. Rempel // Green Chemistry. - 2015. - Vol. 17, № 8. - С. 4401-4410. - Bibliogr. : p. 4409-4410 (30 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): BOND ACTIVATION -- INHIBITORS -- HYDROGEN Аннотация: In this paper we wish to report a highly selective and benign method for the double C-H/C-H coupling of azaaromatics with indoles or pyrrole in the presence of air oxygen/TiO2, as an effective photocatalytic oxidative system. It has been shown that this versatile approach can be applied for direct C-H functionalisation of a variety of azaaromatic systems, such as mono-, di- and triazines, substituted and unsubstituted azines and their benzo-annelated analogues. \\\\expert2\\nbo\\Green Chemistry\\2015, v.17, N 8, p.4401-4410.pdf |
C 75 Construction of Heteroacenes with Fused Thiophene and Pyrrole Rings via the Fischer Indolization Reaction [Electronic resource] / R. A. Irgashev, A. A. Karmatsky, G. L. Rusinov, V. N. Charushin // Organic Letters. - 2016. - Vol. 18, № 4. - С. 804-807 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): FUSED THIOPHENE -- PYRROLE RINGS -- FISCHER INDOLIZATION REACTION Аннотация: A convenient approach to ladder-type 6H-benzo[4',5']thieno[2',3':4,5]thieno[3,2-b]indoles, e.g., I (X-rays single crystal structure shown), bearing various substituents in both terminal benzene rings has been developed. The protocol suggested for prepg. these N,S-heteroacenes is based on using easily available reagents, such as cinnamic acids and arylhydrazines, which can be involved in the Fischer indole synthesis, as the key step. A similar condensed system of 12H-benzo[4'',5'']thieno[2'',3'':4',5']thieno[2',3':4,5]thieno[3,2-b]indole, bearing six rings, has also been obtained. \\\\expert2\\nbo\\Organic Letters\\2016, v.18, N 4, p.804-807,pdf.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 |
Benzo[ b]selenophene/thieno[3,2-b]indole-based n,s,se-heteroacenes for hole-transporting layers / M. S. Demina, N. A. Rasputin, R. A. Irgashev [и др.] // ACS omega. - 2020. - № 5. - С. 9377-9383 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Two series of new N,S,Se-heteroacenes, namely, 6H-benzo[4′,5′]selenopheno[2′,3′:4,5]thieno[3,2-b]indoles and 12H-benzo[4″,5″]selenopheno[2″,3″:4′,5′]thieno[2′,3′4,5]thieno[3,2-b]indoles, were successfully obtained using an effective strategy based on Fiesselmann thiophene and Fischer indole synthesis. The new molecules exhibit a large optical band gap (2.82 eV Egopt 3.23 eV) and their highest occupied molecular orbital (HOMO) energy formed by the plane Ï-core ranges between-5.2 and-5.6 eV, with the narrower optical band gap and lower HOMO level corresponding to selenated heteroacenes. In thin solid films of the heteroacenes, hole mobility measured using the conventional CELIV technique ranges between 10-5 and 10-4 cm2·V-1·s-1. All these make the proposed condensed-ring compounds a promising platform for the development of hole-transporting materials applicable in organic electronics. |
Aryne-mediated transformations of 5-perfluorophenyl-substituted 3-(pyridin-2-yl)-1,2,4-triazines / T. D. Moseev, M. V. Varaksin, E. A. Nikiforov [et al.] // Actual problems of organic chemistry and biotechnology. - Екатеринбург, 2020. - P274-276 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): PYRIDO[1,2-A]INDOLES -- ARYNE -- REARRANGEMENT |
Photosphysical properties of green-emitting polyfluorinated 10-(1h-1,2,3-triazol-1-yl)pyrido[1,2-a]indole fluorophores / T. D. Moseev, M. V. Varaksin, D. A. Gorlov [et al.] // Actual problems of organic chemistry and biotechnology. - Екатеринбург, 2020. - P271-273 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): PYRIDO[1,2-A]INDOLES -- FLUOROPHORES |
C-H/C-H coupling of 4h-imidazole-3 oxides with indoles in the synthesis of bifunctional azaheterocyclic derivatives / N. F. Vaskina, E. A. Nikiforov, T. D. Moseev [et al.] // Современные синтетические методологии для создания лекарственных препаратов и функциональных материалов : сборник тезисов VI Международной конференции. - Екатеринбург, 2022. - Ст. I-28. - P79 Рубрики: ХИМИЧЕСКИЕ НАУКИ |
Synthesis of heteroannulated indolopyrazines through domino N-H palladium-catalyzed/metal-free oxidative C-H bond activation / Y. A. Kvashnin, E. V. Verbitskiy, E. F. Zhilina [et al.] // ACS Omega. - 2020. - Vol. 5, № 25. - P15681-15690 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A convenient approach to [1,2,5]oxadiazolo[3′,4′:5,6]pyrazino[2,3-b]indoles and their heteroannulated analogues bearing various aryl substituents in the backbone has been developed. This synthetic protocol is based on Pd-catalyzed Buchwald–Hartwig and subsequent annulation by intramolecular oxidative cyclodehydrogenation. The photophysical properties for new polycycles have been measured. |