S 98 Rusinov, G. L. Synthesis of 2-substituted 6,8-dinitro[1,2,4]triazolo[1,5-a]pyridines and the formation of the related zwitterionic sigma-adducts [Electronic resource] / G. L. Rusinov, V. L. Mikhailov, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 1999. - Vol. 48, № 7. - P1391-1393 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A method for the synthesis of 2-substituted 6,8-dinitro[1,2,4]triazolo[1,5-a]pyridines is proposed. The method includes the reaction of 2-chloro-3,5-dinitropyridine with the corresponding 5-substituted tetrazoles. The resulting compounds react with anhydro bases of ?- and ?-methylazinium salts to give zwitterionic ?-adducts. \\\\Expert2\\nbo\\Russian Chemical Bulletin\\1999, 48 (7), 1391.pdf |
L 87 Long-range 1H-15N J couplings providing a method for direct studies of the structure and azide-tetrazole equilibrium in a series of azido-1,2,4-triazines and azidopyrimidines [Electronic resource] / T. S. Shestakova, Z. O. Shenkarev, S. L. Deev , O. N. Chupakhin, L. A. Khamidullina, V. L. Rusinov, A. S. Arseniev // Journal of Organic Chemistry. - 2013. - Vol.78, №14. - P6975-6982. - Библиогр.: с. 6981-6982 (43 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): AMPLITUDE-MODULATED -- COUPLING CONSTANTS -- NITROUS ACID Аннотация: The selectively 15N labeled azido-1,2,4-triazine 2*A and azidopyrimidine 4*A were synthesized by treating hydrazinoazines with 15N-labeled nitrous acid. The synthesized compounds were studied by 1H, 13C, and 15N NMR spectroscopy in DMSO, TFA, and DMSO/TFA solutions, where the azide-tetrazole equilibrium could lead to the formation of two tetrazoles (T, T′) and one azide (A) isomer for each compound. The incorporation of the 15N label led to the appearance of long-range 1H-15N coupling constants (JHN), which can be measured easily by using amplitude-modulated 1D 1H spin-echo experiments with selective inversion of the 15N nuclei. The observed JHN patterns enable the unambiguous determination of the mode of fusion between the azole and azine rings in the two groups of tetrazole isomers (2*T′, 4*T′ and 2*T, 4*T), even for minor isoforms with a low concentration in solution. However, the azide isomers (2*A and 4*A) are characterized by the absence of detectable J HN coupling. The analysis of the JHN couplings in 15N-labeled compounds provides a simple and efficient method for direct NMR studies of the azide-tetrazole equilibrium in solution \\\\expert2\\NBO\\Journal of Organic Chemistry\\2013, v.78, p.6975.pdf |
S 98 Synthesis and antiviral activity of nonannulated tetrazolylpyrimidines / V. A. Ostrovskii, G. G. Danagulyan, O. M. Nesterova [et al.] // Chemistry of Heterocyclic Compounds. - 2021. - Vol. 57, № 4. - P448–454
Кл.слова (ненормированные): PYRIMIDINES -- TETRAZOLES -- BIOLOGICAL ACTIVITY -- LINKERS Аннотация: Nonannulated tetrazolylpyrimidines in the structure of which the heterocyclic fragments are separated by hydrazinocarbonylmethyl, methylpyrazolyl groups or a sulfur atom were synthesized. Some of these compounds showed moderate in vitro activity against H1N1 subtype of influenza A virus. The selectivity index of the anti-influenza action of {5-[(4,6-dimethylpyrimidin-2-yl)sulfanyl]-1H-tetrazol1-yl}acetic acid, which has very low cytotoxicity, was twice as high as the selectivity index of the reference drug rimantadine. |