S 98 Synthesis of 7-alkyl(aryl)-6-alkoxycarbonyl-5-fluoroalkyl-1,2,4-tri(tetr)azolo[1,5-a]pyrimidines [Electronic resource] / M. V. Pryadeina, Ya. V. Burgart, V. I. Saloutin, M. I. Kodess, E. N. Ulomskii, V. L. Rusinov // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2004. - Vol. 40, № 6. - P902-907. - Библиогр. : с. 906 (14 назв.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Fluorinated 3-oxo esters react with aldehydes and 3-amino-1,2,4-triazoles and 5-aminotetrazoles to give, respectively, 7-alkyl(aryl)-6-alkoxycarbonyl-5-fluoroalkyl-1,2,4-triazolo[1,5-a]pyrimidines and -tetra-zolo[1,5-a]pyrimidines. The same heterocyclic products can be obtained by reaction of 2-benzylidene-2-fluoroacyl esters with the corresponding aminoazoles \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2004, 40 (6), 902-907.pdf |
F 70 Fluoroalkyl-containing lithium beta-diketonates in the synthesis of 1,2,4-triazolo[1,5-a]pyrimidines [Electronic resource] / O. A. Kuznetsova, V. I. Filyakova, K. I. Pashkevich, E. N. Ulomskii, P. V. Plekhanov, G. L. Rusinov, M. I. Kodess, V. L. Rusinov // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2003. - Vol. 52, № 5. - P1190-1194 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Cyclocondensation of fluorine-containing lithium beta-diketonates with 3-amino-1,2,4-triazoles afforded 7-fluoromethyl-1,2,4-triazolo[1,5-a]pyrimidines \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2003, 52 (5), 1190.pdf |
N 91 Nucleophilic ring-opening of the azole and azine moieties in 6-nitro-1,2,4-triazolo[1,5-a]pyrimidin-7-ones [Electronic resource] / E. N. Ulomskii, V. V. Voronin, V. L. Rusinov, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2001. - Vol. 50, № 4. - P682-688 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The effects of the nature of the nucleophile and the structure of 6-nitrotriazolo[1,5-a]pyrimidinones on the direction of the ring opening were investigated. The triazole ring is opened under the action of strong bases, such as alkoxides or alkalis, to form 2-cyanoaminopyrimidinones and then 2-aminopyrimidinones. The results of the reactions with N-nucleophiles depend on the accessibility of position 5 of the heterocycle. Thus, sterically hindered secondary amines react with 5-methyltriazolopyrimidinones to give 2-guanidinopyrimidinones and then 2-aminopyrimidinones. In the absence of a substituent at position 5, the azine ring is opened to form 4-alkyl-3-amino-1,2,4-triazoles and 3-amino-2-nitroacrylamides. Under the action of primary amines, only the pyrimidine fragment is cleaved \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2001, 50 (4), 682.pdf |
R 30 Reactions of 2-arylhydrazonoacetamidoximes with orthoesters [Electronic resource] / N. P. Belskaia, A. V. Koksharov, S. G. Lesogorova, P. A. Slepukhin, V. A. Bakulev // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2011. - Vol.60, №5. - С. 889-895. - Bibliogr. : p. 895 (11 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): HYDRAZONES -- AMIDOXIMES -- ORTHOESTERS Аннотация: The reactions of 2 arylhydrazono 2 carbamoylacetamidoximes with orthoesters afford either 3 arylhydrazono 1,2,4 oxadiazoles or 1,2,3 triazoles, depending on the reactant structure. \\\\expert2\\NBO\\Russian Chemical Bulletin\\2011, 60 (5), 869-875.pdf |
S 98 Synthesis of Triterpene A-Condensed Azoles [Electronic resource] / N. V. Galaiko, A. V. Nazarov, I. A. Tolmacheva, P. A. Slepukhin, Y. B. Vikharev, O. A. Maiorova, V. V. Grishko // Chemistry of Heterocyclic Compounds. - 2014. - Article in Press Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): ALFA-HYDROXIMINO KETONES -- 1,2,3-TRIAZOLES -- ALLOBETULONE Аннотация: Lupane and 18αH-oleanane α-hydroximino ketones were used to synthesize derivatives condensed at ring A with a substituted azole fragment, namely, C(2)-C(3)-fused oxazoles and 1,2,3-triazoles. Triterpene isoxazoles fused at the C(1)-C(2) bond are described for the first time. An optimized method was proposed for the synthesis of unsubstituted 1,2,3-triazoles, displaying cytotoxic activity (IC50 8.4-40.7 μM) relative to rhabdomyosarcoma, lung carcinoma, and MS melanoma cell lines. |
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 |
S 98 Synthesis of 2-Aryl-1,2,3-triazoles by Oxidative Cyclization of 2-(Arylazo)ethene-1,1-diamines: A One-Pot Approach [Electronic resource] / K. D Gavlik, S. G. Lesogorova, E. S. Sukhorukova, J. O. Subbotina, P. A. Slepukhin, E. Benassi, N. P. Belskaia // European Journal of Organic Chemistry. - 2016. - № 15. - С. 2700-2710 Рубрики: ХИМИЧЕСКАЯ ТЕХНОЛОГИЯ Кл.слова (ненормированные): SYNTHETIC METHODS -- nUCLEOPHILIC ADDITION -- OXIDATIVE DEQUATERNIZATION Аннотация: A one-pot approach for the synthesis of 2-aryl-5-amino-1,2,3-triazoles is reported. This approach involves a tandem nucleophilic addition of alkylamines to hydrazonoyl cyanides and in situ oxidative cyclization of the resulting 2-(aryl-azo)ethene-1,1-diamines in the presence of copper(II) acetate and air. The described one-pot procedure is characterized by good yields, excellent selectivity, methodical simplicity, and uses readily available chemicals. This method was applied to the gram-scale synthesis of 2-aryl-1,2,3-triazoles. \\\\expert2\\NBO\\European Journal of Organic Chemistry\\2016, v. 15, p. 2700.pdf |
R 30 Reactivity of 1,2,3-triazoles towards sulfonyl chlorides. A novel approach to 1-and 2-sulfonyl-4-azolyl-1,2,3-triazoles / T. Beryozkina, I. Efimov, W. M. F. Fabian, N. Beliaev, P. A. Slepukhin, M. L. Isenov, W. Dehaen, G. Lubec, O. S. Eltsov, Z. Fan // Tetrahedron. - 2015. - Vol. 71, № 36. - С. 6189-6195 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): 1,2,3-TRIAZOLES -- SULFONYL CHLORIDES -- 2-SULFONYL-4-AZOLYL-1,2,3-TRIAZOLES \\\\expert2\\NBO\\Tetrahedron\\2015, v. 71 , p. 6189.pdf |
Synthesis and antioxidant activity of new neomenthyl and caranyl thiotriazoles / Y. V. Gyrdymova, D. V. Sudarikov, S. A. Rubtsova, S. A. Patov, A. V. Kuchin, O. G. Shevchenko, P. A. Slepukhin, F. A. Lakhvich, F. S. Pashkovskii // Chemistry of natural compounds. - 2018. - Vol. 54, № 5. - P883-888 Кл.слова (ненормированные): TRIAZOLES -- NEOMENTHANE AND CARANE SULFIDES Аннотация: New neomenthyl and caranyl thiotriazoles were synthesized in up to 80% yields. Studies of the antioxidant and membrane-protective activity of the synthesized compounds in vitro showed that sulfides with a carane moiety were more active than analogs with a neomenthane substituent. |
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. |
Design, synthesis, biological evaluation and molecular docking studies of 1,4-disubstituted 1,2,3-triazoles: peg-400:h2o mediated click reaction of fluorescent organic probes under ultrasonic irradiation / C. K. R. Reddivari, S. R. Devineni, R. R. Yellalavenkata [et al.] // Polycyclic aromatic compounds. - 2021. - Vol. 42, № 7. - P3953-3974 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): ULTRASONICATION -- 123-TRIAZOLE -- ANTIOXIDANT ACTIVITY Аннотация: The perpetual demand of medicinally significant scaffolds has prompted the synthetic chemists to identify simple and efficient routes for flawless synthesis. A PEG-400:H2O mediated highly versatile, efficacious and selective “Click reaction” of fluorescent organic Probes under ultrasonic irradiation is reported. 1,2,3-Triazole ring has also been revealed to play a crucial role in bioorthogonal methodologies, fragment-based drug design, and biomolecular mimetics. This methodology provides a rapid and efficient approach for the synthesis of 1,4-Disubstituted 1,2,3-triazoles under Copper (I)-Catalyzed Azide-Alkyne [3 + 2] Cycloaddition (CuAAC) conditions in good to excellent yields in less time. This synthetic protocol has been proven to endorse easy work-up under benign reaction conditions. The green solvent system employed has been efficaciously reused several times without any loss of its activity in an aqueous medium. All the title compounds were characterized by using elemental analysis, 1HNMR, 13CNMR, FTIR, and mass spectral data. The newly synthesized compounds were biologically evaluated for their antioxidant activity. The antioxidant activity results demonstrate that all compounds showed good to excellent antioxidant activity, particularly the compounds 5d, 8 b, 8c and 8d exhibited promising radical scavenging activity. Further, photophysical properties of the compounds were accomplished using spectrofluorimeter. By this method, compounds 5c, 5e, 5f, 8a, 8 b, 8c and 8d exhibited fluorescence in the visible region. Molecular docking studies suggested the antioxidant activity of synthesized compounds due to the inhibition of neuronal nitric oxide synthase (HnNOS). https://doi.org/10.1080/10406638.2021.1878246 |
4-Hydroxy-3-nitro-1,4-dihydrotriazolo[5,1-c][1,2,4]triazines: synthesis, antiviral activity, and electrochemical characteristics / R. A. Drokin, E. A. Fesenko, P. N. Mozharovskaia [et al.] // Russian chemical bulletin. - 2022. - Vol. 71, № 11. - P2460-2466 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A new method for preparation of 4-hydroxy-3-nitro-1,4-dihydrotriazolo[5,1-c][1,2,4]-triazines using 1-nitro-2-morpholinoethylene and 3-diazo-1,2,4-triazoles is proposed. Antiviral activity against the Coxsackie B3 virus and electrochemical transformations of the prepared compounds are studied. |
An efficient synthesis of push-pull fluorophores based on (2-fluoroaryl)-1,2,3-triazoles / I. A. Lavrinchenko, T. D. Moseev, Y. A. Seleznev [et al.] // Успехи синтеза и комплексообразования = Advances in synthesis and complexing : сборник тезисов шестой Международной научной конференции. - Москва, 2022. - P194 Рубрики: ХИМИЧЕСКИЕ НАУКИ |
Design and synthesis of y-shaped fluorophores based on n(2)-aryl-1,2,3 triazoles / I. A. Lavrinchenko, T. D. Moseev, Y. A. Seleznev [et al.] // Успехи синтеза и комплексообразования = Advances in synthesis and complexing : сборник тезисов шестой Международной научной конференции. - Москва, 2022. - P240 Рубрики: ХИМИЧЕСКИЕ НАУКИ |