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1.
Инвентарный номер: нет.
   
   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
ББК 54
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
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2.
Инвентарный номер: нет.
   
   S 98


   
    Synthesis of pyrimido[1,2-a]indoles (minireview) / I. L. Nikonov, D. S. Kopchuk, G. V. Zyryanov, V. L. Rusinov // Chemistry of Heterocyclic Compounds. - 2021. - Vol. 57, № 10. - P993–995
ББК Г
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: This review considers methods for the synthesis of pyrimido[1,2-a]indoles and their ring-fused derivatives, covering publications from the last 10 years. Depending on the synthons used for assembling the target structure, three main approaches to the synthesis of pyrimido- [1,2-a]indoles can be distinguished: annulation of a pyrimidine ring to 2-aminoindoles, modification of other indole derivatives, and miscellaneous methods.

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3.
Инвентарный номер: нет.
   


   
    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.

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4.
Инвентарный номер: нет.
   
   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.)
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
SYNTHESIS -- CARBINOL LINKED BIS-HETEROCYCLES -- INDOLES

\\\\expert2\\nbo\\Tetrahedron\\2016, v. 72 , p. 227-233.pdf
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5.
Инвентарный номер: нет.
   
   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.)
ББК 54
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
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6.
Инвентарный номер: нет.
   


   
    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

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7.
Инвентарный номер: нет.
   
   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
ББК 54
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
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8.
Инвентарный номер: нет.
   


   
    Mechanochemical synthesis of coumarins via Pechmann condensation under solvent-free conditions: an easy access to coumarins and annulated pyrano[2,3-f] and [3,2-f]indoles / A. D. Sharapov, R. F. Fatykhov, I. A. Khalymbadzha [и др.] // Green Chemistry. - 2022. - Vol. 24, № 6. - P2429-2437
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
A green protocol has been developed for the synthesis of simple coumarins and linear pyrano[2,3-f] and [3,2-f]indoles by the reaction of phenol derivatives with β-ketoesters under ball milling at ambient temperature in the presence of methanesulfonic acid as a mild acid catalyst. The significant advantages of this procedure are high yields, scalability, no use of hazardous acids or solvents, shorter reaction time, ambient temperature, low cost, and straightforward purification without column chromatography. This procedure is associated with high EcoScale metrics and a low E-factor. In contrast to traditional Pechmann condensation procedures, the mechanochemical protocol leads to the synthesis of pyranoindoles with excellent regioselectivity and high yields.

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9.
Инвентарный номер: нет.
   


    Irgashev, R. A.
    An approach to the construction of benzofuran-thieno[3,2- b]indole-cored N,O,S-heteroacenes using fischer indolization / R. A. Irgashev, N. A. Kazin, G. L. Rusinov // ACS omega. - 2021. - Vol. 6, № 47. - P32277-32284
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: A series of 6H-benzofuro[2′,3′:4,5]thieno[3,2-b]indoles were readily synthesized from methyl 3-aminothieno[3,2-b]benzofuran-2-carboxylates using a one-pot procedure with Fischer indolization as the key step. At the same time, 3-aminothieno[3,2-b]benzofuran-2-carboxylates were prepared from 3-chlorobenzofuran-2-carbaldehydes in three steps, including replacement of the Cl atom at the C-3 position of these starting substrates onto the -SCH2CO2Me moiety, conversion of the CHO group at the C-2 position into the CN group, followed by base-promoted cyclization of the formed carbonitrile. The present route was elaborated by us because we failed to obtain directly the desired 3-aminothiophene-2-carboxylate by reaction of 3-chlorobenzofuran-2-carbonitrile with methyl thioglycolate in the presence of various bases. In turn, 3-chlorobenzofuran-2-carbaldehydes were prepared from benzofuran-3(2H)-ones following the Vilsmeier–Haack–Arnold reaction.

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10.
Инвентарный номер: нет.
   


    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

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11.
Инвентарный номер: нет.
   
   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.)
ББК 54
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
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12.
Инвентарный номер: нет.
   
   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
ББК 54
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.

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13.
Инвентарный номер: нет.
   
   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.)
ББК 54
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
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14.
Инвентарный номер: нет.
   
   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
ББК 54
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
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15.
Инвентарный номер: нет.
   
   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
ББК 54
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
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16.
Инвентарный номер: нет.
   
   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
ББК 54
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
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17.
Инвентарный номер: нет.
   


   
    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

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18.
Инвентарный номер: нет.
   
   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.)
ББК 54
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
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19.
Инвентарный номер: нет.
   


   
    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.

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20.
Инвентарный номер: нет.
   
   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
ББК 54
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
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