T 44 The synthesis of N-15 abeled 6-nitro-1,2,4-triazolo[5,1-c][1,2,4]triazin-7-one [Text] / O. N. Chupakhin, E. N. Ulomskii, S. L. Deev, V. L. Rusinov // Synthetic Communications. - 2001. - Vol. 31, № 15. - P2351-2355 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A general method for inclusion of the 15N label into the position 1 of 6-nitro-1,2,4-triazolo[5,1-c][1,2,4]triazin-7-one by using K15NO3 has been developed. |
S 98 Synthesis of fluoroalkyl-containing 1,2,3-triketone 2-hetarylhydrazones and their reactions with hydrazines [Electronic resource] / E. V. Shchegol'kov, Ya. V. Burgart, O. G. Khudina, V. I. Saloutin, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2004. - Vol. 53, № 11. - P2584-2590 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Fluoroalkyl-containing 1,2,3-triketone 2-(2,3-dimethyl-5-oxo-1-phenyl-1,2-dihydropyrazol-4-yl)-, 2-(4-ethoxycarbonylpyrazol-3-yl)-, and 2-(1,2,4-triazol-3-yl)hydrazones were synthesized by the azo coupling reactions of fluorinated 1,3-diketones with the corresponding hetaryldiazonium chlorides. The hetarylhydrazones thus synthesized were subjected to cyclocondensation with hydrazines at the 1,3-dicarbonyl fragment to give 3-fluoroalkyl-4-hetarylazopyrazoles \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2004, 53 (11), 2584-2590.pdf |
R 59 Ring-chain isomerism of ethyl 7-polyfluoroalkyl-7-hydroxy-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylates [] / M. V. Pryadeina, Ya. V. Burgart, V. I. Saloutin, O. N. Chupakhin // Mendeleev Communications. - 2008. - Vol. 18, № 5. - С. 276-277. - Bibliogr. : p.277 (10 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Cyclisation of ethyl 2-ethoxymethylidene-3-oxo-3-polyfluoroalkylpropionates with 3-amino-1H-[1,2,4]triazole gives ethyl 7-polyfluoroalkyl-7-hydroxy-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylates that are subject to ring–chain isomerisation in solution, depending on the solvent and the length of the polyfluoroalkyl substituent, to yield ethyl 3-polyfluoroalkyl-3-oxo-2-{([1,2,4]triazol-3-yl)aminomethylidene}propionates via heterocyclic ring opening at the C(7)–N(8) bond \\\\Expert2\\nbo\\Mendeleev Communications\\2008, v.18, p.276.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 |
R 30 Reactions of β-azolylenamines with sulfonyl azides as an approach to N-unsubstituted 1,2,3-triazoles and ethene-1,2-diamines [Electronic resource] / I. Efimov, V. A. Bakulev, N. Beliaev, M. A. Ezhikova, W. Dehaen, P. A. Slepukhin // European Journal of Organic Chemistry. - 2014. - Vol. 2014, №17. - С. 3684-3689. - Bibliogr. : p. 3689 (49 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): AZIDES -- CYCLOADDITION -- NITROGEN HETEROCYCLES Аннотация: The reactions of β-azolylenamines 1 with sulfonyl azides 2 in acetonitrile furnished 1H-4-(azol-5-yl)-1,2,3-triazoles 3 in yields of 52-93%. β-Benzoylenaminones and β-nitroenamine of type 1 also reacted with tosyl azide to form the same type of products 3, proving the generality and efficiency of the method for the synthesis of N-unsubstituted 1,2,3-triazoles. On the other hand, the reactions of 3-(1-aryl-1,2,3-triazol-5-yl)enamines with tosyl azide in the absence of a solvent afforded a mixture of (E)-1-dimethylamino-2-tosylaminoethenes 5 and N,N-dimethyl-N′- tosylformamidine 6 in yields of 40-50 and 20%, respectively. The formation of a variety of compounds from the reactions of enamines 1 with sulfonyl azides 2 is rationalized by the various possible transformations of the intermediate 5-dimethylamino-1,2,3-triazolines \\\\expert2\\nbo\\European Journal of Organic Chemistry\\2014, № 17. p.3684.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 |
A 53 An unexpected direction of the reaction of hydrazino-1,3,5-triazines with formic acid. Synthesis of (4H-1,2,4-triazol-3-yl)guanidines [Electronic resource] / V. V. Bakharev, V. E. Parfenov, I. V. Ul’yankina, A. V. Zavodskskaya, A. A. Gidaspov, P. A. Slepukhin // Chemistry of Heterocyclic Compounds. - 2015. - Vol. 51, № 11/12. - Bibliogr. : p. 1018 (10 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): NITROGEN HETEROCYCLES -- 1,2,4-TRIAZOLYLGUANIDINES -- DIMROTH REARRANGEMENT Аннотация: A new direction of the reaction of 6-amino-substituted 4-hydrazino-1,3,5-triazin-2(1H)-ones with formic acid was found leading to the formation of N-substituted (4H-1,2,4-triazol-3-yl)guanidines together with the expected 5-amino-substituted 1,2,4-triazolo[1,5-a][1,3,5]-triazin-7-ones as a result of opening of the triazine ring and subsequent decarboxylation of an intermediate of the Dimroth rearrangement. The discovered reaction is of interest as a novel method for the synthesis of N-substituted (4H-1,2,4-triazol-3-yl)guanidines. \\\\expert2\\nbo\\Chemistry of Heterocyclic Compounds\\2015, v.51, N 11-12, p. 1014-1018.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 |
S 98 Synthesis of Assemblies of Isoxazole and Azoles Based on 1,3-Dipolar Cycloaddition Reaction of Enamines with Nitrile Oxides = Cинтез ансамблей изоксазолов c азолами в реакции 1,3-диполярного циклоприсоединения енаминов к нитрилоксидам / I. Efimov, Yu. Shafran, N. N. Volkova, N. Beliaev, P. A. Slepukhin, V. A. Bakulev // Chemistry of Heterocyclic Compounds. - 2016. - Vol. 52, № 9. - С. 743-749. - Bibliogr. : p. 748-749 (32 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): ENAMINES -- ISOXAZOLES -- HYDROXAMOYL CHLORIDES Аннотация: 2-(1,2,3-Thiadiazol-5-yl)enamines and 3-(1,2,3-triazol-4-yl)enaminones react with arylhydroxamoyl chlorides at room temperature with the exclusive formation of 3-aryl-4-(1,2,3-thiadiazol-5-yl)- and [4-(1,2,3-triazol-4-yl)carbonyl]isoxazoles in high yields. The proposed mechanism includes in situ generation of nitrile oxides, which participate in the (3+2)-dipolar cycloaddition reactions leading to the formation of the isoxazole ring. \\\\expert2\\NBO\\Chemistry of Heterocyclic Compounds\\2016, v.52, N 9, p. 743-749.pdf |
T 70 Tokareva, M. A. Reaction of sodium 4-acetyl-1-phenyl-1h-1,2,3-triazol-5-olate with 1,2,3-thiadiazole-4-carboxylic acid hydrazide / M. A. Tokareva, K. L. Obydennov, P. A. Slepukhin, O. A. Vysokova, T. V. Gluchareva // Современные синтетические методологии для создания лекарственных препаратов и функциональных материалов (MOSM2018): вторая международная научно-практическая конференция : материалы и доклады. - Екатеринбург, 2019. - С. 134-135 Рубрики: ХИМИЧЕСКИЕ НАУКИ |
K 79 Kovalev, I. S. Synthesis of tetraiodo-10-(4-phenyl-1H-1,2,3-triazol-1-YL)pyridoindole via benzyne-mediated rearrangement of 6-phenyl-3-(pyridin-2-YL)-1,2,4-triazine / I. S. Kovalev, M. Rahman, G. V. Zyryanov, A. Majee, O. N. Chupakhin // Современные синтетические методологии для создания лекарственных препаратов и функциональных материалов (MOSM2018): вторая международная научно-практическая конференция : материалы и доклады. - Екатеринбург, 2019. - С. 144-145 Рубрики: ХИМИЧЕСКИЕ НАУКИ |
Features of a multicomponent biginelli reaction involving 3-oxobutanoyl-containing podands, aromatic aldehydes, and 1,2,4-triazol-3-amine / E. S. Filatova, O. V. Fedorova, K. A. Chistyakov [et al.] // Chemistry of heterocyclic compounds. - 2020. - Vol. 56, № 1. - P88-91 Кл.слова (ненормированные): DIHYDROPYRIMIDINE -- MONOSUBSTITUTED PODAND -- PODAND -- TRIAZOLO[1,5-А]PYRIMIDINE -- TRIAZOLO[4,3-А]PYRIMIDINE -- TUBERCULOSTATIC ACTIVITY Аннотация: [Figure not available: see fulltext.] A reaction of 3-oxobutanoyl-containing podands with thiophene-2-carbaldehyde (or benzaldehyde) and 3-amino-1,2,4-triazole gave podands featuring a 4,7-dihydro[1,2,4]triazolo[1,5-а]pyrimidine motif. It was established that the process was accompanied by the formation of [4,3-а]-isomers, which occurred in a slight excess during the synthesis of a podand containing a phenyl group at position 7 and, on the other hand, were observed as the minor products during the synthesis of podands bearing a thiophen-2-yl substituent. Trace amounts of monosubstituted podands were also detected, containing a free hydroxy group along with the triazolodihydropyrimidine pharmacophore. |
Aryne-mediated transformations of 5-perfluorophenyl-substituted 3-(pyridin-2-yl)-1,2,4-triazines in the design of novel 10-(1h-1,2,3-triazol-1-yl)pyrido[1,2-a]indole fluorophores / T. D. Moseev, M. V. Varaksin, I. A. Lavrinchenko [и др.] // Tetrahedron. - 2020. - Vol. 76, № 18. - P131147 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): 1,2,3-TRIAZOLES -- ARYNE-MEDIATED TRANSFORMATIONS -- CAOSAMBHWGMFEW-UHFFFAOYSA-N -- CYFQLMLVDSTHGC-UHFFFAOYSA-N -- FLUOROARENES Аннотация: A number of novel fluorinated derivatives of the family of pyrido[1,2-a]indole fluorophores have first been synthesized via the aryne-mediated domino transformations of 5-(perfluorophenyl)-3-(pyridin-2-yl)-1,2,4-triazines. A comprehensive study of photophysical properties of the obtained polyfluoroaryl substituted derivatives, in which polyfluoroaryl, 1,2,3-triazole, and pyridoindole subunits contribute to a joint chromophore system, has shown that these compounds proved to exhibit a fluoresce with green light in acetonitrile solutions. |
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 |
Polyaromatic hydrocarbon (PAH)-based aza-POPOPS: synthesis, photophysical studies, and nitroanalyte sensing abilities / M. S. I. Mohammed, I. S. Kovalev, N. V. Slovesnova [et al.] // International journal of molecular sciences. - 2023. - Vol. 24, № 12. - P10084 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): AZA-POPOPS -- CLICK REACTIONS -- CHEMOSENSORS Аннотация: 1,4-Bis(5-phenyl-2-oxazolyl)benzene (POPOP) is a common scintillation fluorescent laser dye. In this manuscript, the synthesis of 2-Ar-5-(4-(4-Ar'-1H-1,2,3-triazol-1-yl)phenyl)-1,3,4-oxadiazoles (Ar, Ar' = Ph, naphtalenyl-2, pyrenyl-1, triphenilenyl-2), as PAH-based aza-analogues of POPOP, by means of Cu-catalyzed click reaction between 2-(4-azidophenyl)-5-Ar-1,3,4-oxadiazole and terminal ethynyl-substituted PAHs is reported. An investigation of the photophysical properties of the obtained products was carried out, and their sensory response to nitroanalytes was evaluated. In the case of pyrenyl-1-substituted aza-POPOP, dramatic fluorescence quenching by nitroanalytes was observed. |