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   S 98


    Synthesis and antiviral activity of fluorinated 3-phenyl-1,2,4- benzotriazines [Электронный ресурс] / S. K. Kotovskaya, G. A. Zhumabaeva, N. M. Perova, Z. M. Baskakova, V. N. Charushin, O. N. Chupakhin, E. F. Belanov, O. A. Serova // Pharmaceutical Chemistry Journal. - 2007. - Vol.41, №2. - P62-68

ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
CYCLIZATION -- CYTOTOXICITY -- FLUORINATION
Аннотация: New synthetic approaches to fluorinated 3-phenyl-1,2,4-benzotriazines for biological testing have been elaborated. 1-(3,4-Difluorophenyl)-3,5- diphenylformazan (IVa) was synthesized via dinitriding of 3,4-difluoroaniline, followed by azo-addition of the resulting azobenzenediazonium chloride with acetaldehyde phenylhydrazone. 6,7-Difluoro-3-phenyl-1,2,4-benzotriazine (Va) was obtained via intramolecular cyclization of formazan IVa in the presence of BF3/AcOH complex. Monofluoro-substituted 6-R-7-fluoro-3-phenyl-1,2,4- benzotriazine derivatives (Vb-Vq) were prepared by substituting fluorine atom with alkoxides in 3,4-difluoronitrobenzene. Conditions for nucleophilic substitution of the second fluorine atom in benzotriazines V have been established. Fluorinated 3-phenyl-1,2,4-benzotriazines have been tested for antiviral and cytotoxic activity on Vero cell cultures and proved to be active against severe diseases caused by smallpox and some other pathogenic viruses

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   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

ББК 54
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
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   S 98


    Synthesis of polyfluoroalkyl-containing 1-(4-acetoxybutyl)- and 1-(4-hydroxybutyl)pyrazoles and their tuberculostatic activity / A. E. Ivanova, O. G. Khudina, Ya. V. Burgart, V. I. Saloutin, M. A. Kravchenko // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2011. - Vol.60, №11. - С. 2396-2400

ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
SYNTHESIS -- PYRAZOLES -- TUBERCULOSTATIC ACTIVITY
Аннотация: Alkylation of polyfluoroalkyl-containing pyrazoles with 4-bromobutyl acetate in acetone in the presence of potassium carbonate leads to a mixture of isomeric 1-(4-acetoxybutyl)-3-fluoroalkyl- and 1-(4-acetoxybutyl)-5-fluoroalkylpyrazoles, which in a number of cases were successfully separated by HPLC. Deacylation in acidic medium with gaseous hydrogen chloride and in basic medium with gaseous ammonia leads to 1-(4-hydroxybutyl)pyrazoles, which manifest moderate tuberculostatic activity

\\\\Expert2\\nbo\\Russian Chemical Bulletin\\2011, 60 (11), 2396-2400.pdf
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   A 10


    A comparative study on the acylative kinetic resolution of racemic fluorinated and non-fluorinated 2-methyl-1,2,3,4-tetrahydroquinolines and 3,4-dihydro-3-methyl-2H-[1,4]benzoxazines [Electronic resource] / D. A. Gruzdev, E. N. Chulakov, G. L. Levit, M. A. Ezhikova, M. I. Kodess, V. P. Krasnov // Tetrahedron: Asymmetry . - 2013. - Vol.24, №19. - С. 1240-1246. - Bibliogr. : p. 1246 (21 ref.)

ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
RACEMIC FLUORINATED -- 1,2,3,4-TETRAHYDROQUINOLINES -- BENZOXAZINES
Аннотация: The acylative kinetic resolution of racemic 6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline, 7,8-difluoro-3,4-dihydro-3-methyl-2H-[1,4]benzoxazine, and their non-fluorinated analogues with (S)-naproxen and N-phthaloyl-(S)-amino acyl chlorides has been carried out. It has been shown that the presence of fluorine atoms in the aromatic fragment of a heterocyclic amine results in the increasing stereoselectivity of acylation with (S)-naproxen acyl chloride and in a decrease in the efficiency of acylative kinetic resolution using N-phthaloyl-(S)-amino acyl chlorides. A method for the preparation of enantiopure (S)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline (ee >99%) was developed

\\\\expert2\\NBO\\Tetrahedron Asymmetry\\2013, in Press, Corr. Proof, 4 Sept.pdf
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   M 78


    Modification of 2-trifluoromethyl-1H-benzimidazole with hydroxyalkyl substituents [Electronic resource] / E. V. Shchegol'kov, A. E. Ivanova, Ya. V. Burgart, V. I. Saloutin, O. N. Chupakhin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2013. - Vol.49, №3. - P417-420. - Библиогр.: с. 420 (7 ref.)

ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
1H-BENZIMIDAZOLE -- 4-BROMOBUTYL ACETATE -- HYDROGEN CHLORIDE
Аннотация: Alkylation of 2-(trifluoromethyl)-1H-benzimidazole with 4-bromobutyl acetate gave 4-[2-(trifluoromethyl)-1H-benzimidazol-1-yl]butyl acetate which was deacylated by the action of hydrogen chloride in anhydrous ethanol. 4-[2-(Trifluoromethyl)-1H-benzimidazol-1-yl]butan-1-ol thus formed showed a moderate tuberculostatic activity. Alkylation of the title compound with chloromethyloxirane afforded a mixture of 1-chloro-3-[2-(trifluoromethyl)-1H-benzimidazol-1-yl]-propan-2-ol and 1-(oxiran-2-ylmethyl)-2-trifluoromethyl-1H-benzimidazole. A new procedure was proposed for the synthesis of 2-[(2-trifluoromethyl-1Hbenzimidazol-1-yl)methoxy]ethyl acetate

\\\\expert2\\NBO\\Russian Journal of Organic Chemistry\\2013, 49, (3), 417-420.pdf
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   A 10


    A convenient approach to 4,7-dihydrotetrazolo [5,1-c ][1,2,4]triazine synthesis [Electronic resource] / E. V. Shchegol'kov, A. E. Ivanova, Ya. V. Burgart, V. I. Saloutin // Journal of Heterocyclic Chemistry. - 2013. - Vol.50. - PE80-E86

ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
TRIAZINE SYNTHESIS -- 1,3-DICARBONYL -- ISOMERISM
Аннотация: Azo coupling of 1,3-dicarbonyl compounds with tetrazolyl-5-diazonium chloride is used to develop a convenient one-step procedure for the synthesis of 4,7-dihydrotetrazolo[5,1-c][1,2,4]triazines. In contrast to nonfluorinated analogs, 7-hydroxy-7-polyfluoroalkyl-4,7-dihydrotetrazolo[5,1-c][1,2,4]triazines undergo a ring-chain isomerism resulting from the cleavage at the C7 - N7a bond. A distinctive feature of nonfluorinated 4,7-dihydrotetrazolo[5,1-c][1,2,4] triazines is the possibility to dehydration, which is accompanied by an azide rearrangement due to the tetrazole ring cleavage with the formation of tetrazolo[1,5-b][1,2,4]triazines

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   L 79


    Liquid-phase oxidation of trimethylhydroquinone catalyzed by copper(II) chloride in the presence of cellulose inorganic composites [Text] : доклад, тезисы доклада / A. B. Shishmakov, Yu. V. Mikushina, M. S. Valova, O. V. Koryakova, L. A. Petrov // III International Conference "Catalysis: Fundamentals and Application", dedicated to the 100th anniversary of Academician G. K. Boreskov, Novosibirsk, July 4-8 2007 : abstr. . - Novosibirsk, 2007. - P97-98

ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ

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   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.)

ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ

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   A 19


    Acylative kinetic resolution of racemic amines using N-phthaloyl-(S)-amino acyl chlorides [Text] / D. A. Gruzdev, G. L. Levit, V. P. Krasnov, E. N. Chulakov, L. Sh. Sadretdinova, A. N. Grishakov, M. A. Ezhikova, M. I. Kodess, V. N. Charushin // Tetrahedron: Asymmetry . - 2010. - Vol. 21, № 8. - P936-942

ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: A comparative study of the kinetic resolution of racemic 2-methyl-1,2,3,4-tetrahydroquinoline and 2,3-dihydro-3-methyl-4H-1,4-benzoxazine using N-phthaloyl-(S)-amino acyl chlorides as chiral acylating agents is described. Temperature and solvent effects on the stereochemical features have been examined. It has been found that N-phthaloyl-(S)-phenylalanyl and N-phthaloyl-(S)-2-phenylglycyl chlorides bearing aromatic substituents close to the stereogenic centre are more stereoselective acylating agents than N-phthaloyl-(S)-alanyl chloride. For the preparative kinetic resolution of racemic amines N-phthaloyl-(S)-phenylalanyl chloride proved to be the most appropriate chiral acylating agent

\\\\Expert2\\nbo\\Tetrahedron Asymmetry\\2010, v. 21, p.936.pdf
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10.

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   F 62


    Five-membered 2,3-dioxo heterocycles: LXXXV. Synthesis of methyl 1-aryl-4,5-dioxo-3-(1-oxo-3-phenylprop-2-en-1-yl)-4,5-dihydro-1H-pyrrole-2-carboxylates and their reaction with 3-amino-5,5-dimethylcyclohex-2-en-1-ones. Molecular and crystalline structure of 4′-hydroxy-1′-(4-methoxyphenyl)-6,6-dimethyl-3′-(1-oxo-3-phenylprop-2-en-1-yl)-1-phenyl-6,7-dihydrospiro[indole-3,2′-pyrrole]-2,4,5′(1H,1′H,5H)-trione / P. S. Silaichev, V. O. Filimonov, P. A. Slepukhin, A. N. Maslivets // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2012. - Vol.48, №4. - С. 561-565

ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
SYNTHESIS -- CARBOXYLATES -- DIMETHYLCYCLOHEX
Аннотация: Treatment of methyl 2-arylamino-4-oxo-6-phenylhexa-2,5-dienoates with oxalyl chloride gave methyl 1-aryl-4,5-dioxo-3-(1-oxo-3-phenylprop-2-en-1-yl)-4,5-dihydro-1H-pyrrole-2-carboxylates which reacted with 3-benzylamino- and 3-arylamino-5,5-dimethylcyclohex-2-en-1-ones to produce 1′-aryl-1-benzyl- and 1,1′-diaryl-4′-hydroxy-6,6-dimethyl-3′-(1-oxo-3-phenylprop-2-en-1-yl)-6,7-dihydrospiro[indole-3,2′-pyrrole]-2,4,5′(1H,1′H,5H)-triones

\\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2012, 48 (4), 561-565.pdf
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11.

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   T 45


    Thiocarbamoyl chitosan: Synthesis, characterization and sorption of Au(III), Pt(IV), and Pd(II) [Text] / S. YU. Bratskaya, A. Yu. Ustinov, Yu. A. Azarova, A. V. Pestov // Carbohydrate Polymers. - 2011. - Vol. 85, № 4. - P854-861 : ил. - Bibliogr. : p. 860-861 (39 ref.)

ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: Here we suggest a new method of chitosan sulfur derivatives (thiocarbamoylchitosans, TC-chitosans) synthesis via reaction in eutectic two-component system ammonium rodanide–thiourea that allows significant increase of substitution degrees at the reduced time and reagent consumption as compared to conventional synthetic procedures. The sorption properties of TC-chitosans with substitution degrees (DS) from 0.4 to 0.9 toward Au(III), Pt(IV), Pd(II) ions were studied in chloride solutions, including systems with 10 to 1000-fold excess of Fe(III), Cu(II), and Zn(II) over the precious metal ions content. The sorption capacities of TC-chitosans increase with DS and change in the row: Au(III) Pd(II) Pt(IV) ? Cu(II) Fe(III) Zn(II). The maximum sorption capacities of TC-chitosan with DS 0.9 for Pt(IV), Pd(II), and Au(III) were 1.24 mmol/g, 3.43 mmol/g, and 3.81 mmol/g, respectively. Characterization of precious metals oxidation states by the XPS method after the sorption on TC-chitosan revealed that the platinum and gold recovery occurred with reduction of Au(III) to Au(I)/Au(0) and Pt(IV) to Pt(II)????

\\\\Expert2\\nbo\\Carbohydrate Polymers\\2011, v. 85, p.854.pdf
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12.

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   R 30


    Reactions of 3-aminoisoxazolo[4,5-c]coumarin with benzoyl chloride: the first example of a preparative 1,2,4-oxadiazole–oxazole rearrangement [Electronic resource] / V. Ya. Sosnovskikh, V. S. Moshkin, M. Yu. Kornev, M. I. Kodess // Mendeleev Communications. - 2011. - Vol. 21, № 2. - P110-111. - Bibliogr. : p. 111 (7 ref.)

ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: Depending on conditions, reaction of 3-amino-4H-chromeno[3,4-d]isoxazol-4-one with benzoyl chloride gives 4-hydroxy- and/or 4-benzoyloxy-3-(5-phenyl-1,2,4-oxadiazol-3-yl)coumarins, which are rearranged into 2-benzamido-4H-chromeno[3,4-d]oxazol-4-one by heating in DMSO

\\\\Expert2\\nbo\\Mendeleev Communications\\2011, v.21, p.110.pdf
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13.

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   I-55


    Imidazole-containing chitosan derivative: a new synthetic approach and sorption properties [Electronic resource] / A. V. Pestov, S. YU. Bratskaya, Yu. A. Azarova, Yu. G. Yatluk // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2012. - Vol.61, №10. - С. 1959-1964. - Bibliogr. : p. 1963-1964 (33 ref.)

ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
CHITOSAN -- SORBENT -- GOLD(III)
Аннотация: A novel method for the synthesis of a hetaryl containing chelate amino polymer, namely, N (4(5) imidazolylmethyl)chitosan (IMC), with a degree of substitution up to 0.3 was pro posed. The "synthesis in gel" approach involves direct substitution of the hydroxyl group in 4(5) imidazolylmethanol. The structures of these polymers were confirmed by 1H NMR data. For sorption studies, IMC samples were crosslinked with epichlorohydrin and diglycidyl ethers of ethylene glycol and diethylene glycol. The degrees of swelling and sorption properties of the polymers largely depend on the crosslinking agent and the degree of crosslinking. The sorption capacities of IMC for AuIII, PtIV, and PdII ions are higher than those of the nonmodified polymer. The extraction of noble metal ions from chloride solutions becomes more selective with increasing degree of crosslinking. The sorption capacity of IMC for CoII and NiII ions is higher than those of chitosan and its known N heterocyclic derivatives

\\\\expert2\\NBO\\Russian Chemical Bulletin\\2012, 61 (10), 1959-1964.pdf
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14.

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   S 98


    Synthesis of Fe@C nanoparticles containing sulfo groups on their surfaces and study of their aggregation behavior in aqueous media / I. A. Bakhteeva, I. V. Medvedeva, I. V. Byzov [et al.] // Russian chemical bulletin. - 2021. - Vol. 70, № 4. - P722-731

ББК Г
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
MAGNETIC NANOPARTICLES -- IRON-CARBON -- BENZENESULFONIC ACID -- IR SPECTROSCOPY
Аннотация: Magnetic iron nanoparticles (MNPs) encapsulated in a carbon shells and containing sulfo groups on the surface (Fe@C-SO3H) were synthesized. The aggregative stability of aqueous suspensions of the Fe@C-SO3H nanoparticles was studied in solutions of bovine serum albumin and calcium chloride and in phosphate-buffered saline, which simulate blood plasma. It is shown that the Fe@C-SO3H particles practically do not aggregate in the phosphate buffer saline for a long time (several days). On the contrary, MNPs encapsulated in a protein shells using ultrasonic treatment form aggregates up to 110–120 nm in size under these conditions. Suspensions of the Fe@C-SO3H particles are stable in aqueous solutions of calcium chloride in the range of the solid phase concentration between 0.05 and 0.10 g L−1. The results obtained indicate the possibility of using the functionalized Fe@C-SO3H nanoparticles in vitro experiments in biological media.

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15.

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   I-60


    Influence of the degree of chitosan sulfoethylation on the sorption of palladium(ii) chloride complexes from multicomponent solutions / E. I. Kapitanova, A. A. Ibragimova, Y. S. Petrova, A. V. Pestov, L. K. Neudachina // Russian Journal of Applied Chemistry. - 2018. - Vol. 91, № 2. - P297-303

ББК Г
Рубрики: ХИМИЧЕСКИЕ НАУКИ

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16.

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   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.

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    Functionalized trifluoromethyl-containing lithium β-diketonate in the synthesis of homo- and heteronuclear complexes of rare-earth metals / Yu. S. Kudyakova, P. A. Slepukhin, I. N. Ganebnykh [и др.] // Russian Journal of Coordination Chemistry. - 2021. - Vol. 47, № 4. - P280-295
Кл.слова (ненормированные):
β-DIKETONATES -- LANTHANIDES -- 19F NMR SPECTROSCOPY -- MASS SPECTROMETRY
Аннотация: The reactions of functionalized lithium CF3-β-diketonate (LiL) with trivalent rare-earth metal salts in methanol afford homobinuclear and heterobi(tri)nuclear complexes depending on the nature of the transition metal and anion (chlorides, nitrates, and acetates). In the cases of lanthanum(III) and cerium(III), homoleptic complexes [(LnL3)2] are isolated (CIF files CCDC nos. 2031097 (Ia) and 2031102 (Ib)). The reaction of LiL with praseodymium(III) nitrate gives the new trimetallic structure [(LiPrL3)(LiL)(NO3)(H2O)2] (CIF file CCDC no. 2031103 (II)), and the replacement of nitrate by chloride gives [(PrL3)(LiL)(H2O)] (CIF file CCDC no. 2031104 (IIIa)). Regardless of the nature of the anion of the salt in the series from neodymium(III) to ytterbium(III) and yttrium(III), Ln–Li β-diketonates [(LnL3)(LiL)(solv)] (solv is H2O and MeOH) are formed, and their structures are characterized by X-ray structure analysis (CIF files CCDC nos. 2031099 (IIIb), 2031100 (IIIc), 2031098 (IVa), 2031096 (IVc), 2031094 (IVf), 2031101 (IVg), and 2031095 (IVh)). The equilibrium of the diketonate isomeric forms in a solution of deuterated dimethyl sulfoxide is studied by 19F NMR spectroscopy, and the qualitative composition of the polynuclear complexes is determined by mass spectrometry.

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18.

Инвентарный номер: нет.



    Development of the method of polystyrene chloromethylation using the synthesis in gel approach / D. V. Nesterov, A. P. Rodionova, A. V. Mekhaev [et al.] // Russian chemical bulletin. - 2021. - Vol. 70, № 6. - P1149-1153
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
POLYSTYRENE -- CHLOROMETHYLATION -- SYNTHESIS IN GEL
Аннотация: A new method for the preparation of poly(chloromethylstyrene) by synthesis in a gel via treating of linear polystyrene with cyclic formals in thionyl chloride has been developed. The method allows to obtain a polymer with a high degree of functionalization. The degree of chloromethylation depends on the molar ratio of the reagents and the catalyst used. The reactivity of the formals increases in the series 1,3-dioxolane < trioxane < paraform. The composition and structure of polymer products were characterized by elemental analysis, FTIR spectroscopy, and thermogravimetry. It is established that carrying out of chloromethylation in gel allows, in comparison with the known methods, to achieve a greater degree of functionalization faster and with lower consumption of reagents and solvents.

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19.

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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20.

Инвентарный номер: нет.

   N 10


    N-Tosyl-(S)-Prolyl Chloride in Kinetic Resolution of Racemic Heterocyclic Amines [Electronic resource] / D. A. Gruzdev, S. A. Vakarov, G. L. Levit, V. P. Krasnov // Chemistry of Heterocyclic Compounds. - 2014. - Article in Press. - С. 1-13

ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
H-[1,4]BENZOXAZINE -- ACYLATION -- AMINES
Аннотация: The kinetic resolution of racemic heterocyclic amines via acylation with N-tosyl-(S)-prolyl chloride was systematically investigated. It was established that racemic mixtures of aromatic amines could be resolved with high efficiency, while the acylation of 2- and 3-methylpiperidines occurred with low diastereoselectivity. A method for the preparation of enantiomerically pure (3 R)-7,8-difluoro-3-methyl-3,4-dihydro-2 H-[1,4]benzoxazine was developed

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