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1.
Инвентарный номер: нет.
   

   
    Transformations of 4,5-bis(trifluoromethyl)imidazolidin-2-one and its N-substituted analogous in reactions with N,N-dinucleophiles / L. V. Saloutina, A. Y. Zapevalov, M. I. Kodess [et al.] // AIP conference proceedings. - 2022. - Vol. 2390. - Ст. 020069
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
CHEMICAL COMPOUNDS
Аннотация: 4,5-Dihydroxy-4,5-bis(trifluoromethyl)imidazolidin-2-one and its N-methyl(phenyl)-substituted analogous were synthesized by the reaction of perfluorobiacetyl with urea and methyl(phenyl)urea. Depending on a solvent nature and character of the substituent at N-atom of the imidazolidine, different trifluoromethyl-containing heterocycles were obtained in reactions of the imidazolidin-2-ones with thiosemicarbazide and guanidine carbonate: imidazothiazol, 1,2,4-triazines, and hydantoins.

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2.
Инвентарный номер: нет.
   

   
    Reactions of trifluoromethylated imidazolidin-2-ones with urea / L. V. Saloutina, A. Y. Zapevalov, M. I. Kodess [et al.] // AIP conference proceedings. - 2022. - Vol. 2390. - Ст. 020070
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
ISOMERIZATION -- SPECTROSCOPY -- ELEMENTAL ANALYSIS
Аннотация: 1-Phenyl-4,5-dihydroxy-4,5-bis(trifluoromethyl)imidazolidin-2-one was synthesized by the reaction of perfluorobiacetyl with phenylurea. Reaction of the former with urea was studied in comparison with the similar interaction of N-methyl-substituted and unsubstituted analogues. N-phenylimidazolidine was shown to yield trifluoromethylated imidazooxazol and hydantoin when heated with urea in dimethylacetamide, in contrast to unsubstituted analog which gives trifluoromethylated glycoluril under the same conditions. The similar reaction in dioxane led to isomerization of cis-isomers of the starting imidazolidines to corresponding trans-isomers. Structure of the reaction products was proved by IR, 1H, 13C and 19F spectroscopy, HR mass spectrometry, elemental analysis and XRD analysis.

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3.
Инвентарный номер: нет.
   

   
    Acylative kinetic resolution of racemic methyl-substituted cyclic alkylamines with 2,5-dioxopyrrolidin-1-yl (R)-2-phenoxypropanoate / D. A. Gruzdev, S. A. Vakarov, M. A. Korolyova [et al.] // Organic & biomolecular chemistry. - 2022. - Vol. 20, № 4. - P862-869
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: The diastereoselective acylation of a number of racemic methyl-substituted cyclic alkylamines with active esters of 2-phenoxypropanoic acid was studied in detail. The ester of (R)-2-phenoxypropanoic acid and N-hydroxysuccinimide was found to be the most selective agent. The highest stereoselectivity was observed in the kinetic resolution of racemic 2-methylpiperidine in toluene at −40 °C (selectivity factor s = 73) with the predominant formation of (R,R)-amide (93.7% de). To explain the observed stereoselectivity, DFT modelling of the transition states in the reactions of the title acylating agent with 2-methylpiperidine and 2-methylpyrrolidine was performed. The calculated values were in good agreement with experimental data. It has been demonstrated that the acylation proceeds via a concerted mechanism, in which the addition of an amine occurs simultaneously with the elimination of the hydroxysuccinimide fragment. The high stereoselectivity of the (R,R)-amide formation is largely ensured by the lower steric hindrances in the transition states as compared to the formation of (R,S)-amide.

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4.
Инвентарный номер: нет.
   
   P 58

   
    Phosgene-free synthesis of symmetric bis(polyfluoroalkyl) carbonates / A. M. Semenova, M. A. Ezhikova, M. I. Kodess [et al.] // Mendeleev Communications. - 2021. - Vol. 31, № 2. - P257-258
ББК Г
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
TRANSESTERIFICATION -- TITANIUM ALKOXIDES -- POLYFLUOALKANOLS -- DIALKYL CARBONATES -- ORGANOFLUORINE COMPOUNDS
Аннотация: A phosgene-free synthesis of symmetric bis(polyfluoroalkyl) carbonates involves the transesterification of diphenyl carbonate with polyfluoroalkanols promoted by stoichiometric amounts of titanium(iv) alkoxides.

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5.
Инвентарный номер: нет.
   
   N 89

   
    Novel purine conjugates with N-heterocycles: synthesis and anti-influenza activity / V. P. Krasnov, V. V. Zarubaev, D. V. Gruzdev [et al.] // Chemistry of Heterocyclic Compounds. - 2021. - Vol. 57, № 4. - P498-504
УДК
Г
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
6-CHLOROPURINE -- HETEROCYCLIC AMINES -- ANTIVIRAL ACTIVITY -- INFLUENZA A AND B VIRUSES
Аннотация: A number of novel amides were synthesized by coupling of 6-[(9H-purin-6-yl)amino]hexanoic acid to heterocyclic amines. The antiviral activity of the obtained compounds, as well as of purine conjugates in which 7,8-difluoro-3-methyl-3,4-dihydro-2H-1,4-benzoxazine is linked to position 6 of purine through a fragment of ɷ-amino acids with varying lengths of polymethylene chains against influenza A and B viruses was studied in vitro. Purine derivatives have been shown to have moderate activity against influenza A (H1N1) virus. The antiinfluenza activity and cytotoxicity of conjugates with 7,8-difluoro-3-methyl-3,4-dihydro-2H-1,4-benzoxazine depend on the length of the linker fragment.

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6.
Инвентарный номер: нет.
   

   
    New multicomponent approach to polyfluoroalkylated pyrido[1,2-a]pyrimidine derivatives and bis-cyclohexenones / M. V. Goryaeva, S. O. Kushch, O. G. Khudina [et al.] // Journal of fluorine chemistry. - 2021. - Vol. 241. - P109686
Рубрики: ХИМИЧЕСКИЕ НАУКИ

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7.
Инвентарный номер: нет.
   
   K 46

   
    Kinetic resolution of racemic 6-substituted 1,2,3,4-tetrahydroquinaldines with chiral acyl chlorides. Experiment and quantum chemical simulation / E. N. Chulakov, M. A. Korolyova, L. S. Sadretdinova [et al.] // Russian chemical bulletin. - 2021. - Vol. 70, № 5. - P890-899
ББК Г
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: A comparative study of the kinetic resolution (KR) of racemic 6-substituted 2-methyl-1,2,3,4-tetrahydroquinolines with acyl chlorides of (S)-naproxen, N-phthaloyl-(S)-leucine, and (R)-O-phenyllactic acid was carried out. The selectivity factors in the KR of racemic amines with acyl chlorides of (S)-naproxen and (R)-O-phenyllactic acid were shown to be approximately the same and higher than those for the KR of N-phthaloyl-(S)-leucyl chloride. The reasons for the stereodifferentiation in the KR of racemic tetrahydroquinaldines containing groups of different electronic properties by acyl chlorides of three different chiral acids were explained using the DFT method. The conditions for stabilizing π—π interactions of aromatic fragments of the reagents, which do not occur in the same form in the transition state and lead to the minor diastereoisomeric product, are created in the transition state of the faster acylation reaction with (S)-naproxen and (R)-O-phenyllactic acyl chlorides. In the case of the KR of 2-methyl-1,2,3,4-tetrahydroquinoline and 2-methyl-6-methoxy-1,2,3,4-tetrahydroquinoline with N-phthaloyl-(S)-leucyl chloride, the acylation diastereoselectivity is determined, most likely, by conformational factors. The individual (S)-enantiomer of 2-methyl-6-methoxy-1,2,3,4-tetrahydroquinoline of high optical purity was synthesized using the KR of the racemate with (S)-naproxen acyl chloride.

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8.
Инвентарный номер: нет.
   

   
    Synthesis of fluorine-containing n,o-heterocycles on the base of 4,5-bis(trifluoromethyl)imidazolidine-2-ones, 2-aminoethanol and 2-aminophenol / L. V. Saloutina, M. I. Kodess, I. N. Ganebnykh [et al.] // Современные синтетические методологии для создания лекарственных препаратов и функциональных материалов" (MOSM 2021): V международная конференция: сборник тезисов. - Екатеринбург, 2021. - С. PR-96
Рубрики: ХИМИЧЕСКИЕ НАУКИ

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9.
Инвентарный номер: нет.
   

   
    Multicomponent domino reactions for the synthesis of variable hydrogenated imidazo[1,2-a]pyridines / S. O. Kushch, M. V. Goryaeva, E. A. Surnina [et al.] // Asian journal of organic chemistry. - 2021. - № 11. - Pe2021007
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: Autocatalyzed one-pot multicomponent cyclization of polyfluoroalkyl-3-oxo ester and ethylenediamine with aldehyde is an effective approach to octa-, hexa- and tetrahydroimidazo[1,2-a]pyridines generated mainly due to the α,β-unsaturated aldehyde addition, often formed in situ, to the 3-oxo ester methylene fragment, followed by the pyridine backbone closure at one of the carbonyl groups.

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10.
Инвентарный номер: нет.
   
   T 82

   
    Transesterification of dialkyl carbonates with fluorine-containing alcohols / A. M. Semenova, M. G. Pervova, M. A. Ezhikova [et al.] // Russian chemical bulletin. - 2021. - Vol. 70, № 5. - P933-936
ББК Г
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: Reactions of transesterification of dimethyl, diethyl and dibutyl carbonates with 2,2,3,3-tetrafluoroethyl-, 2,2,3,3,4,4,5,5-octafluorobutyl- and 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorohexyl-carbinols were investigated in the presence of various catalysts. It was found that the conversion of starting dialkyl carbonate increases upon increasing the length of fluorine-containing radical in the presence of sodium alkoxide. It was shown that the maximum conversion of dimethyl carbonate (90%) was achieved in its reaction with 2,2,3,3,4,4,5,5-octafluoropentan-1-ol upon using catalysts such as K2CO3, NaOH, and sodium alkoxide. To achieve similar values of the conversion, Ti(OEt)4 and Ti(OiPr)4 should be used in the cases of diethyl and dibutyl carbonates, respectively.

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11.
Инвентарный номер: нет.
   

   
    Mutual kinetic resolution of 3-methyl-3,4-dihydro-2h-1,4-benzoxazines and 2-alkoxyacyl chlorides / S. A. Vakarov, D. Gruzdev, L. S. Sadretdinova, M. I. Kodess, A. A. Tumashov, E. B. Gorbunov, G. L. Levit, V. P. Krasnov // Chemistry of Heterocyclic Compounds. - 2018. - Vol. 54, № 4. - P437-446
Рубрики: ХИМИЧЕСКИЕ НАУКИ

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12.
Инвентарный номер: нет.
   
   N 52

   
    New derivatives of fluorine-containing phenazines / T. I. Filyakova, V. I. Filyakova, A. Ya. Zapevalov, M. I. Kodess, P. A. Slepukhin, V. I. Saloutin, V. N. Charushin // Mendeleev Communications. - 2017. - Vol. 27. - P290-292
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: 1,2-Epoxyperfluorocyclohexane reacts with 3,3’,4,4’-tetraaminobiphenyl (1 : 1 mol / mol) to give 4-(6,6,7,7,8,8,9,9-octafluoro- 6,7,8,9-tetrahydrophenazin-2-yl)benzene-1,2-diamine whose structure was determined by X-ray crystallography. Reactions of the latter with 1,2-epoxyperfluorocyclohexane or benzil bring about new fluorinated phenazine derivatives.

\\\\Expert2\\NBO\\Mendeleev Communications\\2017 v.27 p.290-292.pdf
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13.
Инвентарный номер: нет.
   
   T 19

   
    Tandem A(N)-A(N) reactions in the synthesis of tetrahydrothiazolo[4,5-e][1,2,4]triazines / N. N. Mochul`skaya, P. A. Slepukhin, V. N. Charushin, M. I. Kodess // Mendeleev Communications. - 2016. - Vol. 26, № 5. - С. 375-377. - Bibliogr. : p. 377 (14 ref.)
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
TRIAZINES -- ACETIC ANHYDRIDE -- SYNTHESIS
Аннотация: Reaction of 3-aryl-1,2,4-triazines with S,N-dinucleophilic N-(het)arylthioureas in acetic anhydride at room temperature affords the cyclization products, tetrahydrothiazolo[4,5-e]-[1,2,4]triazines in good yields. The structure of the heterocyclic system thus formed was confirmed by X-ray diffraction analysis.

\\\\expert2\\NBO\\Mendeleev Communications\\2016, v.26, p. 375-377.pdf
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14.
Инвентарный номер: нет.
   
   S 98

   
    Synthesis of 4-arylamino-3-(trifluoromethyl)pyridazines and pyridazino[3,4-b]quinoxalines (as by-products) from 3-aroylmethyl-2-(trifluoromethyl)quinoxalines and hydrazine hydrate / V. Ya. Sosnovskikh, A. V. Safrygin, R. A. Irgashev, M. A. Ezhikova, M. I. Kodess // RSC Advances. - 2016. - Vol. 6. - С. 30056-30069. - Bibliogr. : p. 30069 (14 ref.)
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
SYNTHESIS -- HYDRAZINE HYDRATE -- 4-ARYLAMINO-3-(TRIFLUOROMETHYL)PYRIDAZINES

\\\\expert2\\nbo\\RSC Advances\\2016. Vol. 6, С. 30056.pdf
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15.
Инвентарный номер: нет.
   
   U 50

   
    Uncatalyzed, highly stereoselective addition of a-morpholinostyrene to 3-nitro-2-(trihalomethyl)-2H-chromenes. Synthesis of trans-cis- and trans-trans-3-nitro-4-phenacyl-(2-trihalomethyl)chromanes / V. Yu. Korotaev, I. V. Kotovich, A. Yu. Barkov, I. B. Kutyashev, M. I. Kodess, V. Ya. Sosnovskikh // Tetrahedron. - 2016. - Vol. 72, № 1. - С. 216-226. - Bibliogr. : p. 226 (13 ref.)
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
UNCATALYZED -- STEREOSELECTIVE ADDITION -- SYNTHESIS

\\\\expert2\\NBO\\Tetrahedron\\2016, v. 72 , p. 216-226.pdf
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16.
Инвентарный номер: нет.
   
   A 19

   
    Acylative kinetic resolution of racemic heterocyclic amines with (R)-2-phenoxypropionyl chloride / S. A. Vakarov [и др.] // Tetrahedron: Asymmetry . - 2016. - Vol. 27, № 24. - С. 1231-1237. - Bibliogr. : p. 1236-1237 (15 ref.)
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
HETEROCYCLIC AMINES -- BENZOXAZINES -- 2-METHYLINDOLINE -- KINETIC RESOLUTION
Аннотация: The acylative kinetic resolution of racemic heterocyclic amines such as 3,4-dihydro-3-methyl-2H-[1,4]benzoxazines, 3,4-dihydro-3-methyl-2H-[1,4]benzothiazine, 2-methyl-1,2,3,4-tetrahydro-quinolines and 2-methylindoline with enantiopure (R)-2-phenoxypropionyl chloride has been studied. It has been found that acylation of 3,4-dihydro-3-methyl-2H-[1,4]benzothiazine proceeds with the best stereoselectively when compared with other racemic amines. An efficient method for the preparation of (S)-3,4-dihydro-3-methyl-2H-[1,4]benzothiazine (99.4% ee) via a kinetic resolution protocol was developed. The possibility of recycling (R)-2-phenoxypropionic acid has been demonstrated.

\\\\expert2\\NBO\\Tetrahedron Asymmetry\\2016, v. 27, p.1231.pdf
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17.
Инвентарный номер: нет.
   
   D 53

   
    Diastereoselective acylation of 3,4-dihydro-3-methyl-2H-[1,4]benzoxazines with 2-phenoxy carbonyl chlorides / S. A. Vakarov, D. A. Gruzdev, L. Sh. Sadretdinova, E. N. Chulakov, M. G. Pervova, M. A. Ezhikova, M. I. Kodess, G. L. Levit, V. P. Krasnov // Tetrahedron: Asymmetry . - 2015. - Vol. 26, № 5-6. - С. 312-319
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
CARBONYL CHLORIDES -- DIASTEREOSELECTIVE SYNTHESIS -- dIASTEREOSELECTIVE ACYLATION

\\\\expert2\\NBO\\Tetrahedron Asymmetry\\2015, v. 26, p.312.pdf
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18.
Инвентарный номер: нет.
   
   S 98

   
    Synthesis of enantiomers of 3-methyl- and 3-phenyl-3,4-dihydro-2H-[1,4]benzothiazines and their 1,1-dioxides via an acylative kinetic resolution protocol / D. A. Gruzdev, E. N. Chulakov, L. Sh. Sadretdinova, M. I. Kodess, G. L. Levit, V. P. Krasnov // Tetrahedron: Asymmetry . - 2015. - Vol. 26, № 4. - С. 186-194
ББК 54
Рубрики: БИОЛОГИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
SYNTHESIS -- ENANTIOMERS -- ACYLATIVE KINETIC RESOLUTION

\\\\expert2\\NBO\\Tetrahedron Asymmetry\\2015, v. 26, p.186.pdf
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19.
Инвентарный номер: нет.
   
   S 98

   
    Synthesis, photochemical and luminescent properties of (E)-2-(2-hydroxyarylethylene)-3-phenylquinazolin-4(3H)-ones [Electronic resource] / I. G. Ovchinnikova, G. A. Kim, E. G. Matochkina, M. I. Kodess, N. V. Barykin, O. S. Eltsov, E. V. Nosova, G. L. Rusinov, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2015. - Vol. 63, № 11. - С. 2467-2477. - Bibliogr. : p. 2477 (22 ref.)
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
(E)-2-STYRYLQUINAZOLIN-4(3H)-ONES -- LUMINESCENCE -- ORTHO-HYDROXYSTYRYLQUINAZOLINONES
Аннотация: Photoinduced transformations of 2-styrylquinazolinones in solutions were studied using absorption and NMR spectroscopy methods. A possibility of control of the photochemical isomerization rate of quinazolinone 2-(hydroxyaryl)ethenyl derivatives by changing the pH of the medium was demonstrated. The bases and the solvent nature also affect the luminescence intensity of solutions of these compounds in the wavelength range of 550-650 nm. The differences in the steric organization of the ortho-hydroxystyryldiazinone system in crystals and in solutions related to the turn of the aryl group were found. Their influence on the competing processes of luminescence and photochemical transformation of the ethylene fragment were shown. The fact of reversible photo/thermal E-Z-isomerization was established for (E)-2-(2-hydroxystyryl)-3-phenylquinazolin-4(3H)-one.

\\\\expert2\\nbo\\Russian Chemical Bulletin\\2015, 63 (11), 2467-2477.pdf
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20.
Инвентарный номер: нет.
   
   T 44

   
    The reactions of 2-ethoxymethylidene-3-oxo esters and their analogues with 5-aminotetrazole as a way to novel azaheterocycles / M. V. Goryaeva, Ya. V. Burgart, M. A. Ezhikova, M. I. Kodess, V. I. Saloutin // Beilstein Journal of Organic Chemistry. - 2015. - Vol. 11. - С. 385-391
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
2-ETHOXYMETHYLIDENE-3-OXO ESTERS -- 5-AMINOTETRAZOLE -- AZAHETEROCYCLES

\\\\expert2\\NBO\\Beilstein Journal of Organic Chemistry\\2015, v. 11, p. 385-391.pdf
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