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 |
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. |
C 53 Chloromethyl-, dichloromethyl-, and trichloromethyl-1,2,4-triazines and their 4-oxides: method for the synthesis and tele-substitution reactions with C-nucleophiles [Electronic resource] / D. N. Kozhevnikov, N. N. Kataeva, V. L. Rusinov, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2004. - Vol. 53, № 6. - P1295-1300 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A simple procedure was developed for the synthesis of 1,2,4-triazines and their 4-oxides containing the ClCH2, Cl2CH, or CCl3 group at position 3 by cyclization of 2-aryl-2-hydrazono-1-oximinoethanes with the corresponding chloroacetonitriles. The reaction pathway depends on the number of halogen atoms in the acetonitrile used. The reactions with trichloroacetonitrile, monochloroacetonitrile, and dichloroacetonitrile afford 3-trichloromethyl-1,2,4-triazines, 3-chloromethyl-1,2,4-triazine 4-oxides, and a mixture of the corresponding dichloromethyltriazines and their 4-oxides, respectively. The reactions of 3-trichloromethyl-1,2,4-triazines with indoles and phenols are accompanied by tele-substitution with elimination of halogen from the trichloromethyl group to give 5-indolyl- (or 5-hydroxyphenyl)-3-dichloromethyl-1,2,4-triazines \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2004, 53 (6), 1295-1300.pdf |
Z 99 Zyryanov, G. V. Easy formation of S-N(H) products in reactions of indoles and pyrroles with 3-aryl-1,2,4-triazin-5(2H)-ones in the presence of tosyl chloride [Electronic resource] / G. V. Zyryanov, V. L. Rusinov, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2002. - Vol. 51, № 6. - P1042-1044 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The reactions of 3-aryl-1,2,4-triazin-5(2H)-ones with indoles and pyrroles in the presence of p-toluenesulfonyl chloride afforded 3-aryl-6-hetaryl-1,2,4-triazin-5(2H)-ones in high yields. The latter are products of the nucleophilic substitution of hydrogen \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2002, 51 (6), 1042-1044.pdf |
A 89 Asymmetric induction in the reactions of azinones with C-nucleophiles [Electronic resource] / O. N. Chupakhin, I. N. Egorov, V. L. Rusinov, P. A. Slepukhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2010. - Vol. 59, № 5. - P991-1001 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): TRIAZINONES -- QUINOXALIN -- C-NUCLEOPHILES -- INDOLES Аннотация: Effect of acylating agents on the course of addition of C-nucleophiles to 1,2,4- and 1,3,5-triazinones, as well as to quinoxalin-2(1H)-one, was studied. A series of new azinone derivatives was obtained. A method for the preparation of diastereomerically pure addition products of indoles to 1,2,4-triazinones and quinoxalin-2(1H)-one in the presence of N-Ts-L-amino acid acyl chlorides was suggested \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2010, 59 (5), 991-1001.pdf |
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 |
B 43 Benzyne-mediated rearrangement of 3-(2-pyridyl)-1,2,4-triazines into 10-(1H-1,2,3-triazol-1-yl)pyrido[1,2-a]indoles [Electronic resource] / I. L. Nikonov, D. S. Kopchuk, I. S. Kovalev, G. V. Zyryanov, A. F. Khasanov, P. A. Slepukhin, V. L. Rusinov, O. N. Chupakhin // Tetrahedron Letters. - 2013. - Available online 20 September. - Bibliogr. : p. (20 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): 1,2,4 TRIAZINES -- TRIAZOL -- INDOLES Аннотация: The reaction between 5-R-6-R1-3-(2-pyridyl)-1,2,4-triazines and benzyne generated in situ in toluene under reflux results in the formation of 10-(1H-1,2,3-triazol-1-yl)pyrido[1,2-a]indoles 3 in up to 60% yields instead of the expected 3-R-4-R1-1-(2-pyridyl)isoquinolines 2. The crystal structure of product 3c and the proposed mechanism for the formation of 3 are reported \\\\expert2\\nbo\\Tetrahedron Letters\\2013, v. 54, p. 6427.pdf |
D 40 Denislamova, E. S. Five-membered dioxoheterocycles: XCIX. Reaction of 1-aryl-4-aroyl-5- methoxycarbonyl-1H-pyrrole-2,3-diones with indoles. Crystal and molecular structure of substituted 2-(indol-3-yl)pyrrole [Electronic resource] / E. S. Denislamova, P. A. Slepukhin, A. N. Maslivets // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2014. - Vol.50, №2. - С. 225-228. - Bibliogr. : p. 228 (5 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): DIOXOHETEROCYCLES -- METHOXYCARBONYL -- MOLECULAR STRUCTURE Аннотация: 1-Aryl-4-aroyl-5-methoxycarbonyl-1H-pyrrole-2,3-diones react with indole and 2-methylindole with the formation of methyl 1-aryl-3-aroyl-4-hydroxy-2-(1H- indol-3-yl)-5-oxo-2,5-dihydro-1H-pyrrole-2-carboxylates. Crystal and molecular structure of methyl 3-benzoyl-4-hydroxy-2-(2-methyl-1H-indol-3-yl)-5-oxo-1- phenyl-2,5-dihydro-1H-pyrrole-2-carboxylate was examined \\\\expert2\\nbo\\Russian Journal of Organic Chemistry\\2014, 50, (2), 225-228.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 |
R 30 Reaction of 4,5-dimethoxy-1,2-dehydrobenzene with 3-(Pyridin-2-yl)-1,2,4-triazines [Electronic resource] / D. S. Kopchuk, I. L. Nikonov, G. V. Zyryanov, I. S. Kovalev, O. S. Taniya, V. L. Rusinov, O. N. Chupakhin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2015. - Vol. 85, № 8. - С. 1170-1173. - Bibliogr. : p. 1173 (30 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): ISOQUINOLINE ALKALOIDS -- HETEROCYCLES -- ARYNE Аннотация: Reaction of 3-(pyridin-2-yl)-1,2,4-triazines with aryne intermediate, 4,5-dimethoxy-1,2-dehydrobenzene generated in situ, was investigated. As a result of the interaction products of the 1,2,4-triazine transformation are produced: 2,3-dimethoxy-10-(1H-1,2,3-triazol-1-yl)-pyrido[1,2-a]indoles, and also the products of Diels-Alder aza-reaction, 6,7-dimethoxy-1-(pyridin-2-yl)isoquinolines. \\\\expert2\\nbo\\Russian Journal of Organic Chemistry\\2015, 51, (8), 1170-1173.pdf |
A 81 Aryne approach towards 2,3-difluoro-10-(1H-1,2,3-triazol-1-yl)pyrido[1,2-a]indoles [Electronic resource] / D. S. Kopchuk, I. L. Nikonov, G. V. Zyryanov, E. V. Nosova, I. S. Kovalev, P. A. Slepukhin, V. L. Rusinov, O. N. Chupakhin // Mendeleev Communications. - 2015. - Vol. 25, № 1. - С. 13-14. - Bibliogr. : p. 14 (21 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): HYDROGEN-BONDS -- FLUORINE -- N-OXIDES Аннотация: Reaction between 3-(2-pyridyl)-1,2,4-triazines and in situ generated 4,5-difluorobenzyne in toluene affords 2,3-difluoro-10-(1H-1,2,3-triazol-1-yl)pyrido[1,2-a]indoles. The structure of one representative compound was confirmed by X-ray diffraction analysis. \\\\expert2\\nbo\\Mendeleev Communications\\2015, v.25, p. 13-14.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 81 Aryne approach towards 2,3-difluoro-10-(1H-1,2,3-triazol-1-yl)pyrido[1,2-a]indoles / D. S. Kopchuk, I. L. Nikonov, G. V. Zyryanov, E. V. Nosova, I. S. Kovalev, P. A. Slepukhin, V. L. Rusinov, O. N. Chupakhin // Mendeleev Communications. - 2015. - Vol. 25. - С. 13-14 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): 1H-1,2,3-TRIAZOL-1-YL -- INDOLES -- ARYNE \\\\expert2\\NBO\\Mendeleev Communications\\2015, v.25, p. 13-14.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 of a new class of carbinol linked bis-heterocycles via the reaction of 2-(trifluoroacetyl)chromones with indoles and pyrroles / A. V. Safrygin, R. A. Irgashev, M. A. Barabanov, V. Ya. Sosnovskikh // Tetrahedron. - 2016. - Vol. 72. - С. 227-233. - Bibliogr. : p. 233 (25 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): SYNTHESIS -- CARBINOL LINKED BIS-HETEROCYCLES -- INDOLES \\\\expert2\\nbo\\Tetrahedron\\2016, v. 72 , p. 227-233.pdf |
Irgashev, R. A. A new convenient synthetic route towards 2-(hetero)aryl-substituted thieno[3,2-b]indoles using fischer indolization / R. A. Irgashev, A. S. Steparuk, G. L. Rusinov // Organic & biomolecular chemistry. - 2018. - Vol. 16, № 26. - P4821-4832 Рубрики: ХИМИЧЕСКИЕ НАУКИ |
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 |