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 |
T 82 Transformations of 8-substituted tetrazolo[1,5-a]pyrazines [Electronic resource] / P. A. Slepukhin, G. L. Rusinov, S. Dedeneva, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2007. - Vol. 56, № 2. - P345-350 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The reactions of 8-chlorotetrazolo[1,5-a]pyrazine with N-, O-, and S-nucleophiles involve the ipso substitution of the chlorine atom. Heating of this compound with benzotriazole or phenyltetrazole results in elimination of the nitrogen molecule from one of the tetrazole rings to form new annelated azapentalenes \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2007, 56 (2), 345.pdf |
R 30 Reaction of dinitropolychlorobiphenyls with O- and N-nucleophiles as a new route of reprocessing polychlorobiphenyls [Electronic resource] / T. I. Gorbunova, A. Ya. Zapevalov, V. I. Saloutin, O. N. Chupakhin // Russian Journal of Applied Chemistry. - 2002. - Vol. 75, № 3. - P449-451. - Bibliogr. : p. 451 (11 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): AROMATIC COMPOUND -- DINITROPOLYCHLOROBIPHENYLS -- POLYCHLOROBIPHENYLS -- CHLORINE -- UNCLASSIFIED DRUG Аннотация: The reactivity of a mixture of dinitropolychlorobiphenyls in nucleophilic substitution of aromatic chlorine by polyethyleneoxy and amino groups was studied. New polychlorobiphenyl derivatives were obtained. \\\\Expert2\\nbo\\Russian Journal of Applied Chemistry\\2002, v. 75, N. 3, p.449.pdf |
R 30 Reactions of polychlorodiphenyls with alcohols [Text] / T. I. Gorbunova, A. Ya. Zapevalov, V. E. Kirichenko, V. I. Saloutin, O. N. Chupakhin // Russian Journal of Applied Chemistry. - 2000. - Vol. 73, № 4. - P650-654. - Bibliogr. : p. 654 (12 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): ALCOHOL -- BIPHENYL -- POLYCHLORINATED BIPHENYL -- ALKOXY GROUPS Аннотация: Procedures are proposed for chemical treatment of commercial polychlorodiphenyls through nucleophilic substitution of two chlorine atoms by various alkoxy groups. |
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 |
S 67 Slepukhin, P. A. Structural study of the CoCl2 complex with 8(-2-butylthioethyl)oxyquinoline [Electronic resource] / P. A. Slepukhin, D. G. Kim, V. N. Charushin // Russian Journal of Coordination Chemistry. - 2010. - Vol. 36, № 8. - P615-617 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Complex [CoCl(L)]2(Cl)2 (L = 8-(2-butylthioethyl)oxyquinoline) is studied by X-ray diffraction analysis. The empirical formula of the compound is C30H34Cl4Co2N2O2S2, the crystals are monoclinic, a = 9.9382(13) A, b = 11.9097(8) A, c = 14.5715(11) A = 102.511(9)°, Z = 2, space group P21/c. The complex is dimeric with bridging chlorine atoms, and the heterocyclic ligand L is tridentate-cyclic \\\\Expert2\\nbo\\Russian Journal of Coordination Chemistry\\2010, v. 36, N. 8, p.615.pdf |
R 45 Research into the Possibility of Converting HCL to Molecular Chlorine with the Use of a Nanosecond Electron Beam [Text] / M. E. Balezin, I. A. Buldakov, S. Yu. Sokovnin, V. A. Simakina, I. Puzyrev, Yu. G. Yatluk // 15th International Symposium on Hight-Current Electronics : Proceedings . - Tomsk, 2008. - P512-514. - Bibliogr. : p. 514 (18 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ |
O-97 Oxidation of polyfunctional sulfides with chlorine dioxide [Electronic resource] / I. P. Loginova, K. S. Rodygin, S. A. Rubtsova, P. A. Slepukhin, A. V. Kuchin, V. A. Polukeev // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2011. - Vol. 47, № 1. - P124-130 : рис., табл. - Bibliogr. : p. 129-130 (24 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: 3-Benzylsulfanyl-4,5-diphenyl-4H-1,2,4-triazole, 5-methylsulfanyl-1-phenyl-1H-tetrazole, 2-methylsulfanyl-1H-benzimidazole, 2-benzylsulfanyl-1H-benzimidazole, and 1-butylsulfanyl-4-nitrobenzene were oxidized to the corresponding sulfoxides with chlorine dioxide using different modes of oxidant supply. The oxidation process was characterized by high chemoselectivity \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2011, 47 (1), 124-130.pdf |
O-97 Oxidation of 1-methyl-1H-imidazole-2-thiol with chlorine dioxide [] / O. M. Lezina, S. A. Rubtsova, D. V. Belykh, P. A. Slepukhin, A. V. Kutchin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2013. - Vol.49, №1. - С. 112-118 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): CHLORINE DIOXIDE -- OXIDATION CONDITIONS -- IMIDAZOLIUM CHLORIDE Аннотация: Oxidation of 1-methyl-1H-imidazole-2-thiol with chlorine dioxide was performed for the first time, and the results were shown to depend on the oxidation conditions. Optimal conditions were found for the preparation of 1-methylimidazole-2-sulfonic acid, 2,2′-disulfanediylbis(1-methylimidazole) hydrochlorite, and 1-methyl-3-sulfo-3H-imidazolium chloride. A new salt, 4-methylanilinium 1-methyl-1H-imidazole-2-sulfonate, was isolated \\\\Expert2\\NBO\\Russian Journal of Organic Chemistry\\2013, 49, (1), 112-118.pdf |
P 80 Polychlorinated biphenyls: Correlation between experimental data and quantum-chemical simulation / T. I. Gorbunova, J. O. Subbotina, V. I. Saloutin, O. N. Chupakhin // Russian Journal of General Chemistry. - 2014. - Vol.84, №3. - С. 486-495. - Bibliogr. : p. 494-495 (43 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): POLYCHLORINATED BIPHENYLS -- SOVOL MIXTURE -- NUCLEOPHILIC SUBSTITUTION Аннотация: In order to comprehend the data on reactivity of polychlorinated biphenyls of the Sovol mixture in nucleophilic substitution reactions we have performed quantum-chemical simulation using the RB3LYP\6-31G(d) gas phase approximation. Using the "Atoms-in-Molecules" approach, we have computed charges on the biphenyl carbon atoms adjacent to chlorine; furthermore, absolute chemical hardness and global electrophilicity index have been determined for the studied chlorobiphenyls. The calculated descriptors have been correlated with experimentally determined reactivity of the biphenyls in the hard acid-hard base nucleophilic reactions. The higher reactivity of more chlorinated substrates has been confirmed \\\\expert2\\nbo\\Russian Journal of General Chemistry\\2014, V. 84, N 3, p. 486–495.pdf |
O-97 Oxidation of terpenoid diols with chlorine dioxide. Easy preparation of α-hydroxyketones [Electronic resource] / L. L. Frolova, A. V. Popov, L. V. Bezuglaya, P. A. Slepukhin, A. V. Kuchin // Russian Journal of General Chemistry. - 2014. - Vol.84, №5. - С. 853-859. - Bibliogr. : p. 859 (16 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): CHLORINE DIOXIDE -- OXIDATION -- SELECTIVITY Аннотация: Oxidative dehydrogenation of vicinal diols of bornane and pinane type with chlorine dioxide in dimethylformamide has yielded α-hydroxyketones with high selectivity. 3α-Hydroxy-10β-pinane-4-one has been prepared for the first time with yield of 63-65%; the product structure has been confirmed by X-ray diffraction studies \\\\expert2\\nbo\\Russian Journal of General Chemistry\\2014, V. 84, N 5, p. 853–859.pdf |
B 12 Bacterial degradation of a mixture obtained through the chemical modification of polychlorinated biphenyls by polyethylene glycols / D. O. Egorova, T. I. Gorbunova, M. G. Pervova, V. A. Demakov // Applied Biochemistry and Microbiology. - 2014. - Vol. 50, № 7. - С. 722-729. - Bibliogr. : p. 729 (29 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): BACTERIAL DEGRADATION -- CHEMICAL MODIFICATION -- POLYETHYLENE GLYCOLS Аннотация: Polychlorinated biphenyls (PCBs), also known by the trade name Sovol, are toxic industrial wastes. They have been subjected to chemical treatment by polyethylene glycols (PEGs) and potassium hydroxide. As a result of the interaction of the Sovol with various molecular mass PEGs (MMPEG-4 ∼ 200, MMPEG-22 ∼ 1000), water-soluble mixtures M1 and M2 containing mono(polyethylene glycol)oxy-derivatives (PCB-PEG-4 and PCB-PEG-22), polychlorobiphenylols, and unreacted PCB congeners (PCB 44, PCB 47, PCB 49, PCB 52, and PCB 66) were obtained. It was shown for the first time that mixtures M1 and M2 are susceptible to bacterial degradation without their fractionation. According to the gas-liquid chromatography with flame-ionization and mass-spectrometric detection, the Rhodococcus wratislaviensis KT112-7 strain degraded all of the chemical compounds occurring in the mixtures. In a 5-day experiment, it was found that the KT112-7 strain decomposes mono(polyethylene glycol)oxy-derivatives completely (by 100%) and polychlorobiphenylols and PCB congeners by 90–95% in the M1 and M2 mixtures. The culture medium did not contain transformation products, whereas free chlorine ions were accumulated (72–94% of the maximum possible amount). Thus, the use of the chemical modification and consecutive bacterial degradation provided an effective destruction of technical PCB mixtures with a high content of highly chlorinated congeners \\\\expert2\\nbo\\Applied Biochemistry and Microbiology\\2014, v.50, N 7, p.722-729.pdf |
F 33 Features of polychlorinated biphenyls nitration [Electronic resource] / T. I. Gorbunova, M. G. Pervova, K. A. Plotnikova, V. I. Saloutin, O. N. Chupakhin // Russian Journal of General Chemistry. - 2015. - Vol. 85, № 7. - С. 1611-1616. - Bibliogr. : p. 1616 (21 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): POLYCHLORINATED BIPHENYLS -- GAS CHROMATOGRAPHY -- NITRATION Аннотация: Nitration of mono-, di-, and trichlorobiphenyls has been studied. The nitration degree depends on the number of chlorine substituents; one to four nitro groups can be introduced. The conclusions have been confirmed by results of nitration of the "Trikhlorbifenil" technical mixture of polychlorinated biphenyls. \\\\expert2\\nbo\\Russian Journal of General Chemistry\\2015, V. 85, N 7, p. 1611-1616.pdf |
S 98 Synthesis of novel purin-6-yl conjugates with heterocyclic amines linked via 6-aminohexanoyl fragment [Electronic resource] / E. V. Verbitskiy, E. M. Cheprakova, P. A. Slepukhin, M. A. Kravchenko, S. N. Skornyakov, G. L. Rusinov, O. N. Chupakhin, V. N. Charushin // Mendeleev Communications. - 2015. - Vol. 25. - С. 412-414. - Bibliogr. : p. 414 (30 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): 2-AMINOPURINE -- PURIN-6-YL -- HETEROCYCLIC AMINES Аннотация: Novel conjugates of purine and 2-aminopurine linked with heterocyclic amines, including chiral derivatives of 3,4-dihydro- 2H-[1,4]benzoxazine, 3,4-dihydro-2H-[1,4]benzothiazine and 1,2,3,4-tetrahydroquinoline, by 6-aminohexanoyl fragment at the 6-position of purine moiety were obtained. For this purpose, replacement of the chlorine atom in 2-amino-6-chloropurine or 6-chloropurine by direct nucleophilic substitution reaction with 6-aminohexanamides or the coupling of 6-(purin-6-ylamino)-6- hexanoic acid with nitrogen heterocycles were used. \\\\expert2\\nbo\\Mendeleev Communications\\2015, v.25, p. 412.pdf |
R 30 Reactions of Terpene Alcohols and Diols with Chlorine Dioxide in Dimethylformamide [Electronic resource] / L. L. Frolova, A. V. Popov, L. V. Bezuglaya, I. N. Alekseev, P. A. Slepukhin, A. V. Kutchin // Russian Journal of General Chemistry. - 2016. - Vol. 86, № 3. - С. 613-621 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): ONE-POT SYNTHESIS -- OXIDATION -- KETONES Аннотация: The system chlorine dioxide-dimethylformamide in combination with or without a catalytic amount of MoCl5, CeCl3, ZrOCl2, or VO(acac)(2) induces oxidative chlorination of a number of bicyclic terpene alcohols and vicinal diols. 2 alpha-Chloropinan-3-one, 3 alpha-chloro-10 beta-pinan-4-one, 5 alpha-chloro-3 alpha-hydroxycaran-4-one, 5 beta-chloro-3 beta-hydroxycaran-4-one, and 4 alpha-chloro-2 alpha-hydroxypinan-3-one were thus synthesized in good preparative yields. \\\\expert2\\NBO\\Russian Journal of General Chemistry\\2016, V. 86, N 3, p. 613-621.pdf |
S 83 Stereochemical aspects in the synthesis of novel N-(purin-6-yl)dipeptides as potential antimycobacterial agents / V. V. Musiyak, I. A. Nizova, E. N. Chulakov [et al.] // Amino Acids. - 2021. - Vol. 53, № 3. - P407-415 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): DIPEPTIDES -- RACEMIZATION -- PURINE -- COUPLING -- NUCLEOPHILIC SUBSTITUTION -- ANTIMYCOBACTERIAL ACTIVITY Аннотация: The synthesis of purine conjugates with natural amino acids is one of the promising directions in search for novel therapeutic agents, including antimycobacterial agents. The purpose of this study was to synthesize N-(purin-6-yl)dipeptides containing the terminal fragment of (S)-glutamic acid. To obtain the target compounds, two synthetic routes were tested. The first of them is based on coupling of N-(purin-6-yl)-(S)-amino acids to dimethyl (S)-glutamate in the presence of carbodiimide coupling agent followed by the removal of ester groups. However, it turned out that this coupling process was accompanied by racemization of the chiral center of N-(purin-6-yl)-α-amino acids and in all cases led to mixtures of (S,S)- and (R,S)diastereomers (6:4). Individual (S,S)-diastereomers were obtained using an alternative approach based on the nucleophilic substitution of chlorine in 6-chloropurine or 2-amino-6-chloropurine with corresponding dipeptides as nucleophiles. The enantiomeric purity of the target compounds was confirmed by chiral HPLC. To test the assumption that racemization of the chiral center of N-(purin-6-yl)-α-amino acids occurs with the participation of nitrogen atoms of the imidazole ring via the stage of formation of a chirally labile intermediate, we obtained such structural analogs of N-(purin-6-yl)-(S)-alanine as N-(9-benzylpurin-6-yl)-(S)-alanine and N-(7-deazapurin-6-yl)-(S)-alanine. It was found that coupling of these compounds to dimethyl (S)-glutamate was also accompanied by racemization. This indicates that the imidazole fragment does not play a crucial role in this process. When testing the antimycobacterial activity of some of the obtained compounds, conjugates with moderate activity against the laboratory Mycobacterium tuberculosis H37Rv strain (MIC 3.1–6.25 μg/mL) were identified. |
New nido-carborane-containing conjugates of purine: synthesis and antiviral activity / D. A. Gruzdev, A. A. Telegina, V. A. Ol’shevskaya [et al.] // Russian chemical bulletin. - 2022. - Vol. 71, № 11. - P2375-2382 Рубрики: ЗДРАВООХРАНЕНИЕ. МЕДИЦИНСКИЕ НАУКИ ХИМИЧЕСКИЕ НАУКИ Аннотация: New purine derivatives containing a nido-carborane fragment were synthesized by nucleophilic substitution of chlorine atom in 6-chloropurine and 2-amino-6-chloropurine under the action of nido-carborane-containing amines. Compounds with significant activity against the acyclovir-resistant strain of herpes simplex virus type 1, as well as with moderate activity against influenza viruses A and B, were discovered for the first time among the synthesized nido-carboranyl derivatives of purine. |
Synthesis of pyrimidine conjugates with 4-(6-amino-hexanoyl)-7,8-difluoro-3,4-dihydro-3-methyl-2h-[1,4] benzoxazine and evaluation of their antiviral activity / V. P. Krasnov, V. V. Musiyak, G. L. Levit [et al.] // Molecules. - 2022. - Vol. 27, № 13. - Ст. 4236 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): PYRIMIDINE Аннотация: A series of pyrimidine conjugates containing a fragment of racemic 7,8-difluoro-3,4-dihydro-3-methyl-2H-[1,4]benzoxazine and its (S)-enantiomer attached via a 6-aminohexanoyl fragment were synthesized by the reaction of nucleophilic substitution of chlorine in various chloropyrimidines. The structures of the synthesized compounds were confirmed by 1H, 19F, and 13C NMR spectral data. Enantiomeric purity of optically active derivatives was confirmed by chiral HPLC. Antiviral evaluation of the synthesized compounds has shown that the replacement of purine with a pyrimidine fragment leads to a decrease in the anti-herpesvirus activity compared to the lead compound, purine conjugate. The studied compounds did not exhibit significant activity against influenza A (H1N1) virus. |