R 45 Research of Nanosized Metal Oxide Action on Regio- and Stereoselectivity of the Multicomponent Hantzsch Reaction [Text] / Yu. A. Titova, O. V. Fedorova, I. G. Ovchinnikova, M. S. Valova, O. V. Koryakova, G. L. Rusinov, V. N. Charushin // IV International Conference "Multi-Component Reactions and Related Chemistry", Ekaterinburg, 24-28 May 2009. - Екатеринбург, 2009. - PS 44 Рубрики: ХИМИЧЕСКИЕ НАУКИ |
C 31 Catalytic effect of nanosized metal oxides on the Hantzsch reaction [Text] / O. V. Fedorova, O. V. Koryakova, M. S. Valova, I. G. Ovchinnikova, Yu. A. Titova, G. L. Rusinov, V. N. Charushin // Kinetics and Catalysis. - 2010. - Vol. 51, № 4. - P566-572 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): METAL OXIDES -- HANTZSCH REACTION -- ALUMINUM OXIDES Аннотация: The effect of nanosized copper and aluminum oxides, which have a higher sorption capacity than that of bulk samples, on the Hantzsch reaction was studied. The adsorption of starting benzaldehydes and ethyl acetoacetate on the surface of copper and aluminum nanooxides resulted in the activation of these molecules and accelerated the Hantzsch reaction. In addition, considerable activation of ammonia and intermediates (chalcone and enamine) on the surface of aluminum nanooxide facilitated an increase in the rate and selectivity of the process. The experimental results were used to develop a one-pot method for the preparation of nifedipine and nitrendipine \\\\Expert2\\nbo\\Kinetics and Catalysis\\2010, v. 51, N 4, p. 566-572.pdf |
N 21 Nanosized metal oxides as stereoselective catalysts of the Hantzsch and Biginelli reactions [Text] : доклад, тезисы доклада / O. V. Fedorova, I. G. Ovchinnikova, V. G. Kharchuk, G. L. Rusinov, M. A. Uimin, A. A. Mysik, A. A. Ermakov, C. K. Rhee, V. N. Charushin // III International Conference "Catalysis: Fundamentals and Applications", dedicated to the 100-th annivas. of acad. G. K. Boreskov, Novosibirsk, July 4-8, 2007 : abstr. . - Novosibirsk, 2007. - Vol. II. - P44-45 : рис. Рубрики: ХИМИЧЕСКИЕ НАУКИ |
C 31 Catalytic effect of nanosized metal oxides in the Biginelli reaction [Text] / O. V. Fedorova, M. S. Valova, Yu. A. Titova, I. G. Ovchinnikova, A. N. Grishakov, M. A. Uimin, A. E. Ermakov, G. L. Rusinov, V. N. Charushin // Kinetics and Catalysis. - 2011. - Vol. 52, № 2. - P226-233. - Bibliogr. : p. 233 (21 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The effect of nanosized metal oxides on the regio- and stereoselectivity of the multicomponent Biginelli reaction and the reaction mechanism under conditions of heterogeneous catalysis were studied. It was found that the considerable activation of reagents occurred on the surface of metal nanooxides. The Biginelli reaction occurred by two mechanisms: a carbocationic mechanism took place along with the generally accepted mechanism (through the N-acyliminium ion). Nanosized metal oxides in the presence of chiral inductors increased the regio- and stereoselectivity of the Biginelli reaction \\\\Expert2\\nbo\\Kinetics and Catalysis\\2011, v. 52, N 2, p. 226.pdf |
U 62 Unusual heterocyclization of chalcone podands with 3-amino-1,2,4-triazole / I. G. Ovchinnikova, M. S. Valova, E. G. Matochkina, M. I. Kodess, A. A. Tumashov, P. A. Slepukhin, O. V. Fedorova, G. L. Rusinov, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2011. - Vol.60, №5. - С. 965-974 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): TEMPLATE SYNTHESIS -- CHALCONE PODAND -- CROWN ETHERS Аннотация: A new type of intramolecular cyclization of 1,5-bis[2-(E-3-oxo-3-phenylprop-1-enyl)-phenoxy]-3-oxapentane with 3-aminotriazole promoted by potassium ions was discovered. A cascade mechanism for the formation of crownophane with 4,7-dihydro[1,2,4]triazolo[1,5-a]-pyrimidine fragment was suggested. Effects of oligooxyethylene fragment of the chalcone podand and acid-base catalysis on the selectivity of the cyclocondensation processes and degree of oxidation of triazolopyrimidine fragments were studied. The product structures were confirmed by IR, 1H and 13C NMR spectroscopy and X-ray diffraction study \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2011, 60 (5), 965-974.pdf |
R 45 Research of Nanosized Metal Oxide Action on Regio- and Stereoselectivity of the Multi-component Hantzsch Reaction / Yu. A. Titova, O. V. Fedorova, I. G. Ovchinnikova, M. S. Valova, O. V. Koryakova, G. L. Rusinov, V. N. Charushin // Advances in Experimental Medicine and Biology . - 2011. - Vol.699, Session 1 : Catalysis and Muiti-Component Reactions. - С. 1-29. - bibliogr.: p. 29 (2 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): SYNTHESIS -- HETEROGENEOUS CATALYSIS -- NANOOXIDE |
S 98 Synthesis of 4-(thien-2-yl)-substituted coumarins through Lewis acid catalyzed Michael addition of thiophenes to 3-benzoylcoumarins followed by oxidation [Electronic resource] / R. A. Irgashev, A. A. Karmatsky, G. L. Rusinov, V. N. Charushin // Tetrahedron Letters. - 2014. - Vol.55, №26. - С. 3603-3606 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): THIOPHENES -- 3-BENZOYLCOUMARINS -- Lewis acid Аннотация: 3-Benzoyl-4-(thien-2-yl)coumarins have been obtained in good yields according to the SNH addition–oxidation protocol, involving the diastereoselective addition of thiophenes at C-4 of 3-benzoylcoumarins under BBr3 catalysis, followed by oxidation of the intermediate 3,4-trans-3-benzoyl-4-(thien-2-yl)-3,4-dihydrocoumarins with DDQ. This two-step procedure can be regarded as nucleophilic substitution of hydrogen (SNH) on the heterocyclic ring of coumarins \\\\expert2\\nbo\\Tetrahedron Letters\\2014, v. 55, p. 3603.pdf |
S 90 Studying of nanosized metal oxide action on stereoselectivity of the Biginelli reaction / Yu. A. Titova, O. V. Fedorova, O. N. Zabelina, G. L. Rusinov, A. Yu. Vigorov, V. P. Krasnov, V. N. Charushin // Materials of the 10th Congress on Catalysis Applied to Fine Chemicals. - Turku (Finland), 2013. - С. 33 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): METAL OXIDES -- NANOSIZED METAL OXIDES -- BIGINELLI REACTION |
T 44 The synthesis of planar chiral ferrocenes and their use for an effective asymmetric catalysis / O. N. Chupakhin, I. A. Utepova, V. N. Charushin, A. A Musikhina, P. O. Serebrennikova // 18th European Symposium on Organic Chemistry ESOC-2013, Marseille, France, 7-12 July 2013 : book of abstracts. - Marseille, France, 2013. - С. 224 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): SYNTHESIS -- CHIRAL FERROCENES -- EFFECTIVE ASYMMETRIC CATALYSIS |
E 27 Effect of nanosized TiO2–SiO2 covalently modified by chiral molecules on the asymmetric Biginelli reaction [Electronic resource] / Yu. A. Titova, O. V. Fedorova, G. L. Rusinov, A. Yu. Vigorov, V. P. Krasnov, A. Murashkevich, V. N. Charushin // Catalysis Today. - 2015. - Vol. 241. - С. 270-274. - Bibliogr. : p. 274 (23 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): NANOOXIDE TiO2–SiO -- BIGINELLI REACTION -- ASYMMETRIC CATALYSIS Аннотация: The method for immobilization of chiral molecules (menthol and proline derivatives) on the mixed nanooxide TiO2–SiO2 surface has been developed. The synthesized nanocomposites were used as catalysts of the Biginelli reaction. It was shown that inactive chiral molecules, when covalently bonded to the nanooxide surface, acquired properties of a chiral inducer in the asymmetric Biginelli reaction. \\\\expert2\\nbo\\Catalysis Today\\2015, v.241, p.270.pdf |
Methodology of C(sp2)-H functionalization in mono- and diazine N-oxides in the synthesis of heterocyclic meso-substituted calixarenes [Electronic resource] / M. V. Varaksin, O. N. Chupakhin, V. N. Charushin, K. A. Khlamkin, I. A. Utepova // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2015. - Vol. 6, № 5. - С. 1093-1096 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): MESO-SUBSTITUTED CALIXARENES -- MESO-SUBSTITUTED AZINYLCALIXARENES -- METAL CATALYSIS Аннотация: Earlier unknown meso-substituted azinylcalixarenes were obtained by a direct cross-coupling of 2-lithium-25,26,27,28-tetramethoxycalix[4]arenes with mono- and diazine N-oxides without transition metal catalysis. \\\\expert2\\nbo\\Russian Chemical Bulletin\\2015, 64 (5), 1093-1096.pdf |
A 89 Asymmetric Biginelli Reaction Catalyzed by Silicon, Titanium and Aluminum Oxides [Electronic resource] / O. V. Fedorova, Yu. A. Titova, A. Yu. Vigorov, M. S. Toropova, O. A. Alisienok, A. Murashkevich, V. P. Krasnov, G. L. Rusinov, V. N. Charushin // Catalysis Letters. - 2016. - Vol.146, № 2. - С. 493-498 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): BIGINELLI REACTION -- PHENYLETHYLAMINE -- ALUMINUM OXIDES Аннотация: The asym. Biginelli reaction was investigated in the presence of N-[(2S,4R)-4-hydroxyprolyl]-(S)-1-phenylethylamine as chiral inducer and silicon, titanium or aluminum oxides (individual and mixed, bulk and nanosized) as heterogeneous catalysts. The synthesis of Et (4R)-6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate from benzaldehyde, urea and Et acetoacetate has been described. It has been shown that all studied oxides improve chemo- and stereoselectivity of the Biginelli reaction. \\\\expert2\\nbo\\Catalysis Letters\\2016, v.146, p.493.pdf |
Synthesis and physicochemical and catalytic properties of composites in the Sio2–Zro2 system / A. N. Murashkevich, O. A. Alisienok, E. S. Novik [et al.] // Inorganic materials. - 2020. - Vol. 56, № 4. - P430-436 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): ACID-BASE PROPERTIES -- CATALYSIS -- COMPOSITE -- SILICA -- SPECIFIC SURFACE AREA -- ZIRCONIA Аннотация: Using coprecipitation, a sol–sol method, and molecular layering, we have synthesized SiO2–ZrO2 composites with SiO2 : ZrO2 ratios from 1 : 1 to 9 : 1 and a large specific surface area, which increases with growth silicon-containing component concentration. Using adsorption of Hammett indicators, we have assessed the concentration of acid–base centers in the pK range 1.3–9.6, which has been shown to vary from 68 to 160 μmol/g. Elemental analysis and IR spectroscopy data have demonstrated the presence of not only water but also nitrate ions and carbon dioxide on the surface of the samples. It has been shown that the use of nanoparticulate SiO2–ZrO2 oxides as heterogeneous catalysts—promoters for (2S,4R)-4-hydroxyprolyl-(S)-1-phenylethylamine trifluoroacetate, a chiral inducer in the asymmetric Biginelli reaction, makes it possible to raise ee (enantiomeric excess) from 39 to 68% and the reaction yield from 29 to 55%. |
Стереоселективный синтез дигидропиримидинтионового поданда в присутствии L-пролина или 4-гидрокси-L-пролина и нитратов металлов / Е. С. Филатова, О. В. Федорова, И. Г. Овчинникова [и др.] // Известия Академии наук. Серия химическая. - 2022. - № 7. - С. 1506-1513 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): ПОДАНД ДИГИДРОПИРИМИДИНТИОНСОДЕРЖАЩИЙ -- НИТРАТЫ МЕТАЛЛОВ -- СТЕРЕОСЕЛЕКТИВНАЯ РЕАКЦИЯ БИДЖИНЕЛЛИ Аннотация: Исследована асимметрическая реакция Биджинелли с участием 3-оксобутаноилсодержащего поданда, бензальдегида и тиомочевины с использованием вторичных аминов в качестве хирального индуктора, кислоты Бренстеда, как катализатора и солей металлов (в особенности, нитратов металлов) в качестве добавки (additive of asymmetric catalysis, AAC). Туберкулостатически активный дигидропиримидинтионсодержащий поданд получен с энантиомерным избытком 57% в присутствии 4-гидрокси-L-пролина. В присутствии нитратов металлов отмечено влияние ионного радиуса катиона на величину энантиоселективного избытка исследуемой реакции, что позволило предложить возможный механизм хиральной индукции, регулируемый комплексообразующей способностью исходного β-кетоэфирсодержащего поданда с ионами металлов и координацией реагентов в переходных состояниях. |
Stereoselective synthesis of dihydropyrimidinethione podand in the presence of L-proline or 4-hydroxy-L-proline and metal nitrates / E. S. Filatova, O. V. Fedorova, I. G. Ovchinnikova [et al.] // Russian chemical bulletin. - 2022. - Vol. 71, № 7. - P1506-1513 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The asymmetric Biginelli reaction involving a 3-oxobutanoyl-containing podand, benzaldehyde, and thiourea was studied using secondary amines as a chiral inductor, Brönsted acid as a catalyst, and metal salts (especially metal nitrates) as an additive of asymmetric catalysis (AAC) was studied. The tuberculostatically active dihydropyrimidine-thione-containing podand was synthesized with an enantiomeric excess of 57% in the presence of 4-hydroxy-L-proline. In the presence of metal nitrates, the influence of the ionic radius of the cation on the enantioselective excess of the reaction under study was observed, which made it possible to propose a possible mechanism of chiral induction controlled by the complexing ability of the initial β-ketoester-containing podand with metal ions and coordination of the reagents in the transition states. |
Radical C–H amination of cyclic nitrones enabled by iodine catalysis / А. A. Akulov, M. V. Varaksin, A. A. Nelyubina [et al.] // Современные синтетические методологии для создания лекарственных препаратов и функциональных материалов : сборник тезисов VI Международной конференции. - Екатеринбург, 2022. - Ст. I-31. - P82 Рубрики: ХИМИЧЕСКИЕ НАУКИ ЗДРАВООХРАНЕНИЕ. МЕДИЦИНСКИЕ НАУКИ |
Oxidative C–H functionalization of arenes: main tool of 21st century green chemistry. A review / A. V. Shchepochkin, F. V. Antipin, V. N. Charushin, O. N. Chupakhin // Doklady Chemistry. - 2021. - Vol. 499, № 1. - P123-157 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Recent advances in the field of direct oxidative C–H functionalization of inactivated arenes, as one of the main tools of green chemistry, are discussed. Examples of building carbon–carbon, carbon–oxygen, carbon–nitrogen, and carbon–sulfur bonds, using catalysis with palladium compounds, oxidation with hypervalent iodine derivatives, and through electrochemical and photochemical transformations, are given. |
The green chemistry paradigm in modern organic synthesis / S. G. Zlotin, K. S. Egorova, V. P. Ananikov [et al.] // Russian Chemical Reviews. - 2023. - Vol. 92. - RCR5104 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): ХИМИЯ ЗЕЛЕНАЯ -- СИНТЕЗ ОРГАНИЧЕСКИЙ Аннотация: After the appearance of the green chemistry concept, which was introduced in the chemistry vocabulary in the early 1990s, its main statements have been continuously developed and modified. Currently, there are 10–12 cornerstones that should form the basis for an ideal chemical process. This review analyzes the accumulated experience and achievements towards the design of chemical products and processes that reduce or eliminate the use or generation of hazardous substances. The review presents the views of leading Russian scientists specializing in various fields of this subject, including homogeneous and heterogeneous catalysis, fine and basic organic synthesis, electrochemistry, polymer chemistry, chemistry based on bio-renewable feedstocks and chemistry of energetic compounds and materials. A new approach to the quantitative evaluation of the environmental friendliness of processes developed by Russian authors is described. |