F 70 Fluorinated lithium 1,3-diketonates as reagents to modify podands and crown-ethers [Electronic resource] / N. S. Boltacheva, O. V. Fedorova, I. G. Ovchinnikova, O. N. Kazheva, A. N. Chekhlov, O. A. Dyachenko, G. L. Rusinov, V. I. Filyakova, V. N. Charushin // Journal of Fluorine Chemistry. - 2007. - Vol. 128, № 7. - P762-768 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Fluorinated enaminoketones, a new type of ligands, bearing two independent coordination centers (polyether's and fluorinated enaminoketones fragments) have been obtained. The crystal structure of the Cu(II) complex of 1,5-bis-[2-(4`,4`,4`-trifluoro-1`-methyl-3`oxo-but-1`-enylamino)-phenoxy]-3-oxapentane (10) has been elucidated by X-ray crystallography. The results obtained show that the complex 10 consists of two crystallographically independent molecules C26H24CuF6N2O5 (A and B), and the metal atom in the complex 10 has four-coordinated arrangement, as a polyhedron with a distorted square with two nitrogen and two oxygen atoms located in corners. \\\\expert2\\nbo\\Journal of Fluorine Chemistry\\2007, v.128. p.762.pdf |
N 85 Nosova, E. V. Cyclization of 2-halobenzoyl chlorides with dinucleophiles as a versatile approach to fused heterocycles [Electronic resource] / E. V. Nosova, G. N. Lipunova, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2004. - Vol. 53, № 6. - P1137-1152 : рис. - Библиогр.: с. 1151-1152 (103 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The review surveys methods for the construction of bi- and polycyclic nitrogen-, oxygen-, and sulfur-containing heterocycles based on reactions of 2-halobenzoyl chlorides with dinucleophiles.?? \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2004, 53 (6), 1137.pdf |
F 70 Fluorine-containing heterocycles. XIX. Synthesis of fluorine-containing quinazolin-4-ones from 3,1-benzoxazin-4-ones [Electronic resource] / A. A. Laeva, E. V. Nosova, G. N. Lipunova, A. V. Golovchenko, N. Yu. Adonin, V. N. Parmon, V. N. Charushin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2009. - Vol. 45, № 6. - P913-920 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Reactions of fluorine-containing 3,1-benzoxazin-4-ones with ammonium acetate, hydrazine, and heteroaromatic amines gave new 3H-, 3-amino-, and 3-hetarylquinazolin-4-ones, respectively. Differences in the conditions of formation of benzoxazinones from anthranilic acids with different fluorination patterns and in the reactions of fluorinated 3,1-benzoxazinones with nitrogen-centered nucleophiles were revealed \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2009, 45 (6), 913.pdf |
F 98 Fused polycyclic nitrogen-containing heterocycles. 11. 4-Hydroxy-3,5-diphenyl-2-phenyliminothiazolidines as new key compounds in the synthesis of thiazolo[3,4-a]quinoxaline derivatives [Electronic resource] / V. A. Mamedov, I. Z. Nurkhametova, S. K. Kotovskaya, Ya. A. Levin, A. T. Gubaidullin, I. A. Litvinov, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2004. - Vol. 53, № 11. - P2568-2576 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A procedure was developed for the synthesis of thiazolo[3,4-a]quinoxaline derivatives based on a new strategy for construction of the pyrazine ring. The key step of the process involves the reaction of 4-hydroxy-3,5-diphenyl-2-phenyliminothiazolidines with o-phenylenediamines \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2004, 53 (11), 2568.pdf |
F 70 Fluoroarenes in the synthesis of benzoannulated nitrogen-containing heterocycles [Electronic resource] / A. A. Layeva, E. V. Nosova, G. N. Lipunova, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2008. - Vol. 57, № 5. - P947-984 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Methods for the synthesis of fluoro-containing benzazoles and benzazines from fluoroarenes (fluoroanilines, fluorobenzoic acids, fluoroacetophenones, fluorophenols, etc.) are described. The potentialities of the most important synthons are considered. Ways of constructing hetero- cycles with fluorine atoms in the annulated benzene fragment are discussed \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2008, 57 (5), 947.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 |
F 98 Fused polycyclic nitrogen-containing heterocycles. 21. Condensation of 4-hydroxy-3,5-diphenyl-2-phenyliminothiazolidine with 5-fluoro-4-morpholino- and 4-(4-methylpiperazino)-1,2-phenylenediamines [Electronic resource] / V. A. Mamedov, N. A. Zhukova, T. N. Beschastnova, A. A. Balandina, A. T. Gubaidullin, S. K. Kotovskaya, Sh. K. Latypov, Ya. A. Levin, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2009. - Vol. 58, № 1. - P203-211 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The condensation of 4-hydroxy-3,5-diphenyl-2-phenyliminothiazolidine with 5-fluoro-4-morpholino- and 5-fluoro-4-(4-methylpiperazino)-1,2-phenylenediamines leads to region-isomeric thiazolo[3,4-a]quinoxalines differing in substituents in positions 7 and 8 of the benzene ring. From the ratio of isomers formed it follows that the mesomeric effect of a fluorine atom in 1,2-phenylenediamines is comparable with the influence of an aminosubstituent \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2009, 58 (1), 203-211.pdf |
U 62 Unusual Expansion of the 1,2,4,5-Tetrazine Ring in [1,2,4]Triazolo[4,3-b]-[1,2,4,5]tetrazines Leading to [1,2,4,6]Tetrazepine Systems [Text] / I. N. Ganebnuikh, S. G. Tolshchina, R. I. Ishmetova, N. K. Ignatenko, P. A. Slepukhin, G. L. Rusinov, V. N. Charushin // European Journal of Organic Chemistry. - 2011. - № 12. - P2309-2318. - Bibliogr. : p. 2318 (22 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Expansion of the tetrazine ring has first been found to occur when [1,2,4]triazolo[4,3-b][1,2,4,5]tetrazines were allowed to react with CH-active compounds in acetonitrile in the presence of triethylamine to give the unexpected series of 8,9-dihydro-7H-[1,2,4]-triazolo[4,3-b][1,2,4,6] tetrazepine derivatives \\\\Expert2\\nbo\\European Journal of Organic Chemistry\\2011, p.2309.pdf |
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 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 |
S 98 Synthesis, structure and complexation of the fluorinated 1,3-enaminoketones containing at the nitrogen atom substituents with a terminal C≡C bond [Electronic resource] / E. F. Zhilina, P. A. Slepukhin, N. S. Boltacheva, M. G. Pervova, D. L. Chizhov, V. I. Filyakova, V. N. Charushin // Russian Journal of General Chemistry. - 2012. - Vol. 82, №12. - P1962-1969 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): SYNTHESIS -- NITROGEN -- TERMINAL C≡C BONDS Аннотация: The reaction of fluorinated lithium 1,3-diketonates with propargylamine hydrochloride and 1,1,1-trifluorpentane-2,4-dione or 1,1,1-trifluoro-4-methoxypent-3-en-2-one with propargylamine and 3-aminophenylacetylene were performed to obtain fluorinated 1,3-enaminones containing at a nitrogen atom substituents with terminal C≡C bonds: (Z)-1,1,1-trifluoro-4-(2-propynylamino)-3-pentene-2-one, (Z)-1,1,2,2-tetrafluoro-5-(2-propynylamino)-4-hexen-3-one, and 4-(3-ethynylphenylamino)-1,1,1-trifluoropentyl-3-en-2-one. Reactions of 4-(3-ethynyl-phenylamino)-1,1,1-trifluoro-pentyl-3-en-2-one with Cu(II) acetate or nanosized powder of copper or its oxides led to the respective chelate complex. The structure of (Z)-1,1,2,2-tetrafluoro-5-(2-propynylamino)-4-hexen-3-one and a copper complex of 4-(3-etinilphenylamino)-1,1,1-trifluoropenta-3-en-2-one was determined by XRD \\\\Expert2\\NBO\\Russian Journal of General Chemistry\\2012, V. 82, N 12, p. 1962–1969.pdf |
B 39 Behavior of Monocyclic 1,2,4-Triazines in Reactions with C-, N-, O-, and S-Nucleophiles [Electronic resource] / V. N. Charushin, S. G. Alexeev, O. N. Chupakhin, H. C. Van der Plas // Advances in Heterocyclic Chemistry. - 1989. - Vol. 46 (C). - С. 73-142. - Bibliogr. : p. 135-142 (200 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): 1,2,4-TRIAZINES -- NITROGEN-CONTAINING HETEROCYCLES Аннотация: Among the six-membered nitrogen-containing heterocycles the 1,2,4-triazines have attracted the attention of chemists for a long time. This is due to the fact that many 1,2,4-triazine derivatives are biologically active and are used in medicine and agriculture. Moreover, 1,2,4-triazines are of chemical interest. They proved to be very susceptible to attack by all kinds of nucleophiles, leading to the addition, and subsequently either substitution or cyclization, and ring transformation. This continuing and lively interest in this area of heterocyclic chemistry has produced a great number of publications and patent applications. This chapter concentrates on the behavior of monocyclic 1,2,4-triazines in reactions with C-, N-, 0-, and S-nucleophiles, because the important features of general character established for simple 1,2,4-triazines can evidently be applied to other derivatives including condensed 1,2,4-triazines. \\\\expert2\\nbo\\Advances in Heterocyclic Chemistry\\1988. V. 46 (C). P. 73-142.pdf |
C 98 Cyclizations of N-alkyl-substituted azinium cations with bifunctional nucleophiles. 28. Orientation of the nucleophile in the reaction of quinoxalinium salts with indan-1,3-dione [Electronic resource] / G. M. Petrova, M. G. Ponizovskii, V. N. Charushin, G. G. Aleksandrov, E. O. Sidorov, O. N. Chupakhin // Chemistry of Heterocyclic Compounds. - 1990. - Vol. 26, № 5. - С. 565-572. - Bibliogr. : p. 572 (12 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): QUINOXALINUM SALTS -- C-NUCLEOPHILES -- AZINIUM CATIONS Аннотация: In reactions with quinoxalinium salts in alcoholic-base media indan-1,3-dione acts as a C nucleophile, adding at the 2 or 3 position of the heterocycle to give the corresponding ylidene derivatives; attack by the nucleophile at the C(3) atom (the Β position relative to the quaternary nitrogen atom) is preceded by addition of alcohol at the a position. Dissociative substitution at the C(2) atom in 2-alkoxy-3-(1,3-dioxoindan-2-ylidene)-1,2,3,4-tetrahydroquinoxalines by another nucleophile makes it possible to regard lyate complexes as probable intermediates in cyclizations of 1,4-diazinium salts with dinucleophiles. \\\\expert2\\nbo\\Chemistry of Heterocyclic Compounds\\1990, v.26, N 5, p.565.pdf |
A 10 A Convenient Approach to CF3-Containing N-Heterocycles Based on 2-Methoxy-2-methyl-5-(trifluoromethyl)furan-3(2H)-one [Electronic resource] / D. N. Bazhin, Yu. S. Kudyakova, G. -V. Roeschenthaler, Ya. V. Burgart, P. A. Slepukhin, M. L. Isenov, V. I. Saloutin, V. N. Charushin // European Journal of Organic Chemistry. - 2015. - № 23. - С. 5236-5245. - Bibliogr. : p. 5245 (23 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): NITROGEN HETEROCYCLES -- FLUORINE -- OXYGEN HETEROCYCLES Аннотация: New synthetic routes to trifluoromethylated N-heterocycles based on condensations of 2-methoxy-2-methyl-5-(trifluoromethyl)furan-3(2H)-one with bifunctional N-nucleophiles are described. For the first time, trifluoromethyl-containing pyrazoles, pyrazolines and isoxazolines bearing hydrazone or oxime groups could be obtained by a one-pot strategy based on reactions of 5-(trifluoromethyl)furan-3(2H)-one with two equivalents of the corresponding hydrazines or hydroxylamine in the presence of an acid. The interaction of furan-3(2H)-one with ureas proceeded under mild conditions to furnish 1H-furo[2,3-d]imidazol-2(3H)-one derivatives in good yield. Further, a trifluoromethyl-containing quinoxaline derivative was obtained by condensation of furan-3(2H)-one with ortho-phenylenediamine. \\\\expert2\\nbo\\European Journal of Organic Chemistry\\2015, №23. p.5236-5245.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 |
N 89 Novel push-pull thieno[2,3-b]indole-based dyes for efficient dye-sensitized solar cells (DSSCs) / R. A. Irgashev, A. A. Karmatsky, G. A. Kim, G. L. Rusinov, V. N. Charushin, A. A. Sadovnikov, V. K. Ivanov, S. A. Kozyukhin, V. V. Emets, V. A. Grinberg // Arkivoc. - 2017. - Vol. 4. - P34-50 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): DYE-SENSITIZED SOLAR CELLS -- ELECTRON-RICH HETEROCYCLES -- METAL-FREE DYES -- PHOTOVOLTAIC PROPERTIES -- PUSH-PULL STRUCTURE -- THIENO[2,3-B]INDOLE Аннотация: New metal-free sensitizers (IK 3-6), based on the thieno[2,3-b]indole ring system, bearing various aliphatic substituents at the nitrogen atom (electron-donating part), several thiophene units (π-bridge linker) and 2-cyanoacrylic acid (the electron-accepting and anchoring group) have been synthesized for application in dye-sensitized solar cells (DSSCs). The relationship between the IK dye structure and efficiency of the corresponding DSSC has been elucidated. Power conversion efficiency (PCE) up to 6.3% (short-circuit photocurrent density (JSC) 19.0 mA cm-2, open-circuit voltage (VOC) 0.59 V, and fill factor (FF) 56.4%) were obtained for the DSSC, based on 2-cyano-3-{5-[8-(2-ethylhexyl)-8H-thieno[2,3-b]indol-2-yl]thiophen-2-yl}acrylic acid (IK 3), which proved to be a highly synthetic available compound, under simulated AM 1.5 G irradiation (100 mW cm-2), thus indicating that thieno[2,3-b]indole-based organic dyes are perspective candidates for DSSCs. \\\\Expert2\\NBO\\ARKIVOC\\2017 v.4 p.34-50.pdf |
Design of fluorescent sensors based on azaheterocyclic push-pull systems towards nitroaromatic explosives and related compounds: a review / E. V. Verbitskiy, G. L. Rusinov, O. N. Chupakhin, V. N. Charushin // Dyes and pigments. - 2020. - Vol. 180. - P108414 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): NITROAROMATIC EXPLOSIVES -- FLUORESCENCE QUENCHING -- PYRIDINES -- PYRAZINE -- PYRIMIDINES -- TRIAZINES Аннотация: Highly sensitive and selective detection of nitro containing high energy organic compounds such as picric acid (PA), 2,4,6-trinitrotoluene (TNT) and 2,4-dinitrotoluene (DNT) has become a challenging task due to concerns over national security, criminal investigations and environment protections. Among various known detection methods, fluorescence sensors have gained special attention in recent time. The family of fluorescent sensors based on push-pull systems that incorporate nitrogen heterocycles as an electron-withdrawing group have a growing interest due to their high sensitivity, selectivity and easy tuning. The fluorescent sensors discussed in this review are classified and organized according to used azaheterocyclic scaffold, their functionality and their ability to detect of nitroaromatics by fluorescence quenching. |
Charushin, V. N. Chemical elements in medicine / V. N. Charushin, Y. A. Titova, E. R. Milaeva // Herald of the Russian academy of sciences. - 2020. - Vol. 90, № 2. - P229-238 Кл.слова (ненормированные): BETA-LACTAM ANTIBIOTICS -- BORON NEUTRON CAPTURE THERAPY -- FLUOROQUINOLONES -- HETEROCYCLES Аннотация: A brief review of chemical elements, compounds from which find application in medicine, ranging from the commonly occurring organogenic elements (carbon, hydrogen, nitrogen, oxygen, sulfur, and phosphorus), composing the structure of proteins and nucleic acids of the cells of living organisms and determining the genetic transmission, to native rarely encountered organic fluorine compounds, synthetic derivatives of which have become firmly ingrained in the arsenal of modern pharmaceutical drugs, is given. Strong emphasis is put on metalloproteins, which play a significant role in the biochemistry of vitally essential processes, as well as metal compounds that are widely used in medicine. Of particular importance are the chemical elements and the isotopes, compounds of which are employed in nuclear medicine for diagnostics and treatment of a wide range of diseases, oncological and cardiovascular in particular. |
A 99 Azapyrene-based fluorophores: synthesis and photophysical properties / O. S. Taniya, A. F. Khasanov, M. V. Varaksin [et al.] // New Journal of Chemistry. - 2021. - Vol. 45, № 45. - P20955-20971 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Azapyrenes are the nitrogen isosteres of pyrene. Based on theoretical and experimental studies, electron–acceptor azapyrene domains may be considered as convenient scaffolds for constructing a large variety of “push–pull” π-conjugated chromophores with pronounced ICT properties. Over the past decade, due to the unrelenting interest in functional materials and modern methodologies such as cross-coupling, peri-annulation, direct C–H-functionalization, etc., methods for the synthesis of aryl(alkyl) K-functionalized azapyrenes and other derivatives have been developed, and their photophysical and electrochemical properties have been studied. This short review aims at critical analysis of the best known/modern methods for the preparation of functionalized azapyrene derivatives, as well as an assessment of their photophysical/electrochemical properties in comparison with the structural and electronic properties of the parent pyrene. |