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Публикации Чарушина В.Н. (4)

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полный	информационный	краткий

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автору	заглавию	году издания	типу документа

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   M 79


    Molecular structures of chalcone podands: A prognosis of photoinduced transformations in the crystals [Text] / I. G. Ovchinnikova, O. V. Fedorova, P. A. Slepukhin, I. A. Litvinov, G. L. Rusinov // Crystallography Reports. - 2009. - Vol. 54, № 1. - P31-39

ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: A series of chalcone podands with the propenone group in the ortho position of the bridging aryl substituent with respect to the oxyethylene fragment is synthesized. The influence of the preorganization of the chalcone podand molecules in crystals on their ability to participate in topochemical reactions is investigated. From analyzing the X-ray structural data, the highest probability of the solid-state photochemical [2 + 2]cycloaddition is predicted for podands with phenyl substituents and the oxyethylene fragment containing two or three oxygen atoms. The X-ray structural data for the chalcone podand C32H26O4 (3a) are as follows: a = 7.904(9) A, b = 14.92(2) A, c = 21.30(3) A, ? = 91.7(1)°, monoclinic system, space group P21/c, Z = 4, V = 2510(5) A3, ? = 1.26 g/cm3, and R = 0.046; C34H30O5 (3b): a = 15.738(9) A, b = 11.889(2) A, c = 15.0830(15) A, ? = 105.47(14)°, monoclinic system, space group C2/c, Z = 4, V = 2720.0(9) A3, ? = 1.266 g/cm3, and R = 0.0418; C32H24N2O8 (4a): a = 17.9416(18) A, b = 10.9703(8) A, c = 41.699(2) A, ? = 105.970(11)°, monoclinic system, space group P21/c, Z = 4, V = 2781.4(5) A3, ? = 1.348 g/cm3, and R = 0.0426; C36H32N2O10 (4c): a = 7.6286(5)A, b = 17.9398(10) A, c = 11.5890(3)A, ? = 95.287(4)°, monoclinic system, space group P21/n, Z = 2, V = 1579.27(14) A3, ? = 1.372 g/cm3, and R = 0.0377; and C28H22O6 (5a): a = 15.6032(10) A, b = 8.1131(5) A, c = 17.7334(11) A, ? = 91.381(5)°, monoclinic system, space group C2/c, Z = 4, V = 2244.2(2) A3, ? = 1.345 g/cm3, and R = 0.0309.

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   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

ББК 54
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
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   S 98


    Synthesis of podands with dihydropyrimidine fragments based on polyethers with terminal acetoacetamide groups [Electronic resource] / E. S. Radionava, O. V. Fedorova, Yu. A. Titova, G. L. Rusinov, V. N. Charushin // Chemistry of Heterocyclic Compounds. - 2015. - Vol. 51, № 5. - С. 478-482. - Bibliogr. : p. 482 (19 ref.)

ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
ACETOACETAMIDE-CONTAINING PODANDS -- DIHYDROPYRIMIDINE-CONTAINING PODANDS -- ACETYLKETENE
Аннотация: Reactions of aliphatic aminopodands having different length of the polyether chain with acetoacetic ester and 2,2,6-trimethyl-4H-1,3-dioxin-4-one were studied. The interaction of aminopodands with acetoacetic ester in toluene upon sonication (60A degrees D) or heating (90A degrees D) gave podands with terminal aminocrotonate fragments. The use of dioxinone at the same temperature allowed to transform aminopodands into aliphatic acetoacetamide-containing podands. An asymmetric podand with 2-pyridone fragment was isolated as byproduct from the reaction of dioxinone with 1,5-diamino-3-oxapentane. A three-component Biginelli reaction of acetoacetamidecontaining podands with benzaldehyde and urea in the presence of catalytic amounts of polyphosphoric acid immobilized on nanosized TiO2-SiO2 oxide surface enabled the synthesis of podands with 1,4-dihydropyrimidin-2-(1De)-one fragments.

\\\\expert2\\nbo\\Chemistry of Heterocyclic Compounds\\2015, v.51, N 5, p. 478-482.pdf
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    Features of a multicomponent biginelli reaction involving 3-oxobutanoyl-containing podands, aromatic aldehydes, and 1,2,4-triazol-3-amine / E. S. Filatova, O. V. Fedorova, K. A. Chistyakov [et al.] // Chemistry of heterocyclic compounds. - 2020. - Vol. 56, № 1. - P88-91
Кл.слова (ненормированные):
DIHYDROPYRIMIDINE -- MONOSUBSTITUTED PODAND -- PODAND -- TRIAZOLO[1,5-А]PYRIMIDINE -- TRIAZOLO[4,3-А]PYRIMIDINE -- TUBERCULOSTATIC ACTIVITY
Аннотация: [Figure not available: see fulltext.] A reaction of 3-oxobutanoyl-containing podands with thiophene-2-carbaldehyde (or benzaldehyde) and 3-amino-1,2,4-triazole gave podands featuring a 4,7-dihydro[1,2,4]triazolo[1,5-а]pyrimidine motif. It was established that the process was accompanied by the formation of [4,3-а]-isomers, which occurred in a slight excess during the synthesis of a podand containing a phenyl group at position 7 and, on the other hand, were observed as the minor products during the synthesis of podands bearing a thiophen-2-yl substituent. Trace amounts of monosubstituted podands were also detected, containing a free hydroxy group along with the triazolodihydropyrimidine pharmacophore.

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    Pseudocyclic form of 4-hydroxypyrrolidine-2-carboxanilide podands with trioxyethylene chain: modeling, conformational search, and nmr analysis / O. Borodina, G. Makarov, A. E. Masunov [et al.] // The journal of physical chemistrY A (Dynamics, kinetics, environmental chemistry, spectroscopy, structure, theory). - 2021. - Vol. 125, № 28. - P6029-6041
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: The 4-hydroxypyrrolidine-2-carboxanilide podand salt demonstrates catalytic activity in asymmetric Biginelli reaction. The systematic search for prevalent conformational state of the cation was carried out by computer simulations in combination with one- and two-dimensional NMR experiments. For that purpose, we proposed a novel algorithm for the generation and selection of conformers based on molecular dynamics and clustering in the space of principal components. The search had found an important trend of the podand to form a pseudocyclic structure with a horseshoe-shaped conformation of the oligooxyethylene fragment. This conformation is stabilized by different types of intramolecular hydrogen bonds between the acidic and basic centers of the two 4-hydroxypyrrolidine-2-carboxanilide residuals (branches). The proposed approach had made it possible to identify the major structural factors, providing a correlation between the calculated and experimental chemical shifts of hydrogen atoms in the 1H NMR spectra of the protonated podand.

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    Combined approach to conformational analysis of 4-hydroxyproline containing podands using NMR and molecular dynamics simulation / G. Makarov, O. Borodina, A. E. Masunov [et al.] // AIP conference proceedings. - 2022. - Vol. 2390. - Ст. 020045
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
METADYNAMICS -- POLYMERS -- AMINO ACID
Аннотация: Conformational analysis of (2S,4R)-4-hydroxyproline-containing podand based on bias-exchange well-tempered metadynamics computation was performed, and the most representative conformers were selected from generated manifold of conformations by two approaches: by direct clustering by GROMOS algorithm and by partitioning conformations according to torsion angles of polyether chain and free energies of conformers.

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    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.

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