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1.

Вид документа : Статья из журнала
Шифр издания : 54/A 10
Автор(ы) : Gruzdev D.A., Chulakov E.N., Levit G. L., Ezhikova M. A., Kodess M. I., Krasnov V. P.
Заглавие : 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
Место публикации : Tetrahedron: Asymmetry . - 2013. - Vol.24, №19. - С. 1240-1246
Примечания : Bibliogr. : p. 1246 (21 ref.)
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Ключевые слова (''Своб.индексиров.''): 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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2.

Вид документа :
Шифр издания : 54/A 10
Автор(ы) : Bogatishcheva N. S., Yarovenko V. N., Levchenko K.S., Kobeleva O. I., Valova T. M., Barachevskii V. A., Struchkova M. I., Shmelin P. S., Krayushkin M. M., Charushin V. N.
Заглавие : A convenient method for the preparation of mono- and bis-substituted photochromic bis(benzothienyl)perfluorocyclopentenes via regioselective Friedel–Crafts acylation
Место публикации : Tetrahedron Letters. - 2012. - Vol.53, №44. - С. 5948-5951
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Ключевые слова (''Своб.индексиров.''): regioselective friedel–crafts acylation--photochrome--benzofurans
Аннотация: The regioselective Friedel–Crafts acylation of 1,2-bis(2-methylbenzo[b]thien-3-yl)hexafluorocyclopentene was developed. Depending on the reaction conditions, mono- or bis(bromoacetyl) derivatives are formed as single products in good yields. Further heterocyclizations involving α-bromoketone moieties gave a series of new photochromic compounds
\\\\Expert2\\nbo\\Tetrahedron Letters\\2012, v. 53, p. 5948.pdf
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3.

Вид документа : Статья из журнала
Шифр издания : 54/A 10
Автор(ы) : Irgashev R. A., Kazin N. A., Kim G. A., Rusinov G. L., Charushin V. N.
Заглавие : A new synthetic approach to fused nine-ring systems of the indolo[3,2-b] carbazole family through double Pd-catalyzed intramolecular C-H arylation [Электронный ресурс]
Место публикации : RSC Advances. - 2016. - Vol. 6, № 74. - С. 70106-70116
Систем. требования: http://apps.webofknowledge.com/full
Примечания : 26.10.16
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Ключевые слова (''Своб.индексиров.''): ight-emitting-diodes --bipolar host materials--hole-transporting materials
Аннотация: A series of new polycyclic compounds bearing the 5,11-dihydroindolo[3,2-b] carbazole ring system, as the common motif of their nine-ring scaffolds, has been successfully prepared with the usage of an efficient two-step strategy, based on the double Friedel-Crafts acylation of 5,11-dihexyl-6,12-di(hetero) aryl-substituted 5,11-dihydroindolo[3,2-b] carbazoles with 2-iodobenzoyl chloride in the presence of SnCl4, followed by regioselective palladium-catalyzed cyclization of the obtained 2,8-bis(2-iodobenzoyl) derivatives into the desired fused 9H-fluoren-9-ones. Some modifications of these nine-ring structures have been performed to afford compounds of the same family bearing the 9H-fluorene fragments. Basic photophysical and electrochemical properties as well as thermal stability of the new fused indolo[3,2-b] carbazole derivatives have been determined.
\\\\expert2\\NBO\\RSC Advances\\2016. Vol. 6, N 74. P. 70106.pdf
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4.

Вид документа : Статья из журнала
Шифр издания : 54/A 10
Автор(ы) : Burgart Ya. V., Kisil' S. P., Saloutin V. I., Chupakhin O. N.
Заглавие : A route to ethyl alfa-pentafluorobenzoyl-beta-oxobutanoate via its copper(II) chelate [Electronic resource]
Место публикации : Mendeleev Communications. - 2001. - Vol. 11, № 2. - С. 76
Систем. требования: http://www.sciencedirect.com/science/article/pii/S0959943601707213
Примечания : 11.10.2011
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: Ethyl 2-pentafluorobenzoyl-3-oxobutanoate has been prepared by the acylation of ethyl acetoacetate with pentafluorobenzoyl chloride via a copper(II) chelate
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5.

Вид документа : Статья из журнала
Шифр издания : 54/A 19
Автор(ы) : Denisova A.V., Bakulev V. A., Dehaen W., Toppet S., Van Meerlent L., Kodess M. I.
Заглавие : Acylation and Carbamoylation of 2-Hydrazinothiazole Derivatives. Identification of Isomeric Structures [Electronic resource]
Место публикации : Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2005. - Vol. 41, № 4. - С. 584-590
Систем. требования: http://www.springerlink.com/content/u82t64215k1317tk/fulltext.pdf
Примечания : 1.11.2011 г.
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: Acylation and carbamoylation of 2-(arylmethylidenehydrazino)- and 2-(aroylhydrazino)thiazoles was performed, and structure of the products was established
\\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2005, 41 (4), 584.pdf
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6.

Вид документа : Статья из журнала
Шифр издания : 54/G 90
Автор(ы) : Gruzdev D.A., Levit G. L., Krasnov V. P.
Заглавие : Acylative kinetic resolution of racemic heterocyclic amines using N-phthaloyl-(S)-amino acyl chlorides with alkyl side chains
Место публикации : Tetrahedron: Asymmetry . - 2012. - Vol.23. - С. 1640-1646
Примечания : Bibliogr.: p. 1645-1646 (15 ref.)
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Ключевые слова (''Своб.индексиров.''): heterocyclic amines --racemic amines--acyl chlorides
Аннотация: A comparative study of the acylative kinetic resolution of racemic 2-methyl-1,2,3,4 tetrahydroquinoline and 3,4-dihydro-3-methyl-2H-[1,4]benzoxazine using N-phthaloyl-(S)-amino acyl chlorides with alkyl side chains has been carried out. The influence of steric factors on the stereoselectivity of the acylation was demonstrated. The (S)-enantiomers of the heterocyclic amines (ee 99%) were obtained in good yields via a kinetic resolution protocol using N-phthaloyl-(S)-leucyl chloride
\\\\expert2\\NBO\\Tetrahedron Asymmetry\\2012, v. 23, p.1640.pdf
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7.

Вид документа : Статья из журнала
Шифр издания : 54/A 19
Автор(ы) : Vakarov S. A., Gruzdev D.A., Chulakov E.N., Sadretdinova L. Sh., Tumashov A. A., Pervova M. G., Ezhikova M. A., Kodess M. I., Levit G. L., Krasnov V. P., Charushin V. N.
Заглавие : Acylative kinetic resolution of racemic heterocyclic amines with (R)-2-phenoxypropionyl chloride
Место публикации : Tetrahedron: Asymmetry . - 2016. - Vol. 27, № 24. - С. 1231-1237
Примечания : Bibliogr. : p. 1236-1237 (15 ref.)
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Ключевые слова (''Своб.индексиров.''): 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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8.

Вид документа : Статья из журнала
Шифр издания :
Автор(ы) : Gruzdev D.A., Vakarov S. A., Korolyova M. A., Tumashov A. A., Chulakov E.N., Ezhikova M. A., Kodess M. I., Levit G. L., Krasnov V. P., Bartashevich E. V.
Заглавие : Acylative kinetic resolution of racemic methyl-substituted cyclic alkylamines with 2,5-dioxopyrrolidin-1-yl (R)-2-phenoxypropanoate
Место публикации : Organic & biomolecular chemistry. - 2022. - Vol. 20, № 4. - С. 862-869
Предметные 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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9.

Вид документа : Статья из журнала
Шифр издания : 54/D 53
Автор(ы) : Vakarov S. A., Gruzdev D.A., Sadretdinova L. Sh., Chulakov E.N., Pervova M. G., Ezhikova M. A., Kodess M. I., Levit G. L., Krasnov V. P.
Заглавие : Diastereoselective acylation of 3,4-dihydro-3-methyl-2H-[1,4]benzoxazines with 2-phenoxy carbonyl chlorides
Место публикации : Tetrahedron: Asymmetry . - 2015. - Vol. 26, № 5-6. - С. 312-319
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Ключевые слова (''Своб.индексиров.''): carbonyl chlorides --diastereoselective synthesis--diastereoselective acylation
\\\\expert2\\NBO\\Tetrahedron Asymmetry\\2015, v. 26, p.312.pdf
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10.

Вид документа : Статья из журнала
Шифр издания : 54/P 93
Автор(ы) : Prokhorov A. M., Makosza M., Chupakhin O. N.
Заглавие : Direct introduction of acetylene moieties into azines by S(N)H methodology
Место публикации : Tetrahedron Letters. - 2009. - Vol. 50, № 13. - С. 1444-1446
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: The N-oxides of azines 1a–g react with lithium and/or potassium acetylides to give the corresponding ethynylazines 2a–g. Reaction with lithium acetylide requires subsequent acylation of the intermediate anionic adduct for rearomatization whereas in the case of potassium acetylide, auto-aromatization takes place??
\\\\Expert2\\nbo\\Tetrahedron Letters\\2009, V. 50, N 13, p.1444.pdf
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11.

Вид документа : Статья из журнала
Шифр издания : 54/D 62
Автор(ы) : Rusinov G. L., Beresnev D. G., Itsikson N. A., Chupakhin O. N.
Заглавие : Direct modification of benzoannelated crown ethers with 1,2,4-triazin-5(2H)-one moieties
Место публикации : Heterocycles. - 2001. - Т. 55, № 12. - С. 2349-2359
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: A convenient method for one-step coupling of benzoannelated crown ethers with 1,2,4-triazinones based on the reaction of nucleophilic addition to unsubstituted carbon atom of the triazine ring has been worked out. It has been shown that the reaction of 3-substituted 1,2,4-triazin-5(2H)-ones (1) with benzocrown ethers (benzo-12-crown-4, benzo-15-crown-5, benzo-18-crown-6) in the presence of acetic or trifluoroacetic anhydride is accompanied by acylation of triazine ring and results in formation of 3-(1-acyl-5-oxo-1,4,5,6-tetrahydro-1,2,4-triazin-6-yl)benzocrown ethers (7-12). The latters were converted to 3-(5-oxo-2,5-dihydro-1,2,4-triazin-6-yl)benzocrown ethers (18-20) using two alternative routes: the elimination of acetic or trifluoroacetaldehyde or the deacylation followed by the oxidation of the 1,4,5,6-tetrahydro derivatives (13-15).
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12.

Вид документа : Статья из журнала
Шифр издания : 54/E 54
Автор(ы) : Krasnov V. P., Levit G. L., Charushin V. N., Kodess M. I., Kalinin V. N., Chupakhin O. N.
Заглавие : Enantiomers of 3-amino-1-methyl-1,2-dicarba-closo-dodecaborane
Место публикации : Tetrahedron: Asymmetry . - 2002. - Vol. 13, № 16. - С. 1833-1835
Примечания : Bibliogr. : p. 1835 (6 ref.)
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: The enantiomers of 3-amino-1-methyl-1,2-dicarba-closo-dodecaborane were prepared by means of resolution of the racemic mixture via acylation by (S)-naproxen chloride followed by separation and subsequent acid hydrolysis of each of the diastereoisomeric amides. Partial racemization of enantiomeric 3-aminocarboranes was observed during acid hydrolysis
\\\\Expert2\\nbo\\Tetrahedron Asymmetry\\2002, v.13, p.1833.pdf
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13.

Вид документа : Статья из журнала
Шифр издания : 54/F 62
Автор(ы) : Konovalova V. V., Shklyaev Yu. V., Slepukhin P. A., Maslivets A. N.
Заглавие : Five-membered 2,3-dioxo heterocycles: LXXVIII. Acylation of fischer's base with aroylketenes. Crystalline and molecular structure of (1E, 3Z)-4-(4-chlorophenyl)-4-hydroxy-1-(1,3,3-trimethyl-2,3-dihydro-1H-indol-2-ylidene)but-3-en-2-one [Electronic resource]
Место публикации : Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2011. - Vol. 47, № 7. - С. 1062-1065
Систем. требования: http://www.springerlink.com/content/u75m7g32w6mj7v67/fulltext.pdf
Примечания : Bibliogr. : p. 1065 (11 ref.). - 1.11.2011 г.
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: Aroylketenes generated by thermolysis of 6-aryl-2,2-dimethyl-4H-1,3-dioxin-4-ones reacted with 1,3,3-trimethyl-2-methylidene-1,3-dihydro-2H-indole (Fischer's base) to produce (1E,3Z)-4-aryl-4-hydroxy-1-(1,3,3-trimethyl-1,3-dihydro-2H-indol-2-ylidene)but-3-en-2-ones. The crystalline and molecular structures of (1E,3Z)-4-(4-chlorophenyl)-4-hydroxy-1-(1,3,3-trimethyl-2,3-dihydro-1H-indol-2-ylidene)but-3-en-2-one were determined by X-ray analysis
\\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2011, 47 (7), 1062.pdf
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14.

Вид документа : Статья из журнала
Шифр издания : 54/F 70
Автор(ы) : Nosova E. V., Lipunova G. N., Laeva A. A., Charushin V. N.
Заглавие : Fluoro-containing heterocycles: Part XIII. Fluoro-containing derivatives of thiazolo[3,2-a]-, benzothiazolo[3,2-a]-, and benzimidazo[3,2-a]quinazolinones [Electronic resource]
Место публикации : Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2005. - Vol. 41, № 11. - С. 1671-1677
Систем. требования: http://www.springerlink.com/content/u21w6654g5j75q05/fulltext.pdf
Примечания : Библиогр. : с. 1677 (22 назв.). - 28.10.2011 г.
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: Reactions of 2-aminothiazole, derivatives of 2-aminobenzothiazole and 2-aminobenzoimidazole with polyfluorobenzoyl chlorides gave rise to acylation products that at heating in the diphenyl ether formed fluoro-containing derivatives of thiazolo[3,2- a]-, benzothiazolo[3,2- a]-, and benzimidazo[3,2- a]quinazolinone.
\\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2005, 41 (11), 1671.pdf
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15.

Вид документа : Статья из журнала
Шифр издания : 54/F 70
Автор(ы) : Kisil' S. P., Burgart Ya. V., Saloutin V. I., Chupakhin O. N.
Заглавие : Fluoroaryl containing beta,beta-dioxoesters in the synthesis of fluorobenzopyran-4(2)-ones
Место публикации : Journal of Fluorine Chemistry. - 2001. - Vol. 108, № 2. - С. 125-131
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: Fluoroaryl containing ?,??-dioxoesters and their copper(II) chelates have been prepared by acylation of ethyl acetoacetate with 2,6-dimethoxy-3,4,5-trifluorobenzoyl, 2-methoxy-3,4,5,6-tetrafluorobenzoyl and pentafluorobenzoyl chlorides. Cyclization of these ?,??-dioxoesters leads to formation of substituted fluorochromones. Depending on conditions, 2-methyl-5-methoxy-6,7,8-trifluoro-3-ethoxycarbonylchromone hydrolyzed to 5-hydroxy-2-methyl-6,7,8-trifluorochromone or 5-hydroxy-2-methyl-6,7,8-trifluorochromone-3-carboxylic acid. The same chromone reacts with morpholine to form a seven-substituted product and ammonium hydroxide to give 3-iminoacetyl-4-hydroxy-5-methoxy-6,7,8-trifluorocoumarin. Hydrolysis of the latter affords 3-acetyl-4-hydroxy-5-methoxy-6,7,8-trifluorocoumarin. Ethyl-2-(2,6-dimethoxy-3,4,5-trifluorobenzoyl)-3-oxobutanoates undergoes ketone-splitting to 1-(2,6-dimethoxy-3,4,5-trifluorophenyl)-1,3-butandione????
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16.

Вид документа : Статья из журнала
Шифр издания : 54/K 46
Автор(ы) : Krasnov V. P., Levit G. L., Bukrina I. M., Andreeva I.N., Sadretdinova L. Sh., Koroleva M. A., Kodess M. I., Charushin V. N., Chupakhin O. N.
Заглавие : Kinetic resolution of (±)-2,3-dihydro-3-methyl-4H-1,4-benzoxazine, (±)-2-methyl-1,2,3,4-tetrahydroquinoline and (±)-2-methylindoline using N-tosyl-(S)-prolyl chloride
Место публикации : Tetrahedron: Asymmetry . - 2003. - Vol. 14, № 14. - С. 1985-1988
Примечания : Bibliogr. : p. 1988 (6 ref.)
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: Acylation of racemic 2,3-dihydro-3-methyl-4H-1,4-benzoxazine, 2-methyl-1,2,3,4-tetrahydroquinoline and 2-methylindoline with N-tosyl-(S)-prolyl chloride resulted in their kinetic resolution with the predominant formation of (R,S)-diastereoisomeric amides, des being 80, 66 and 38%, respectively. Recrystallisation of the amides followed by acid hydrolysis gave individual (R)-enantiomers of heterocyclic amines
\\\\Expert2\\nbo\\Tetrahedron Asymmetry\\2003, v.14, p.1985.pdf
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17.

Вид документа : Статья из журнала
Шифр издания : 54/K 46
Автор(ы) : Krasnov V. P., Levit G. L., Andreeva I.N., Grishakov A. N., Charushin V. N., Chupakhin O. N.
Заглавие : Kinetic resolution of (±)-2-methyl-1,2,3,4-tetrahydroquinoline and (±)-2-methylindoline [Electronic resource]
Место публикации : Mendeleev Communications. - 2002. - Vol. 12, № 1. - С. 27-28
Систем. требования: http://www.sciencedirect.com/science/article/pii/S0959943602705750
Примечания : 12.10.2011
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: The acylation of racemic 2-methyl-1,2,3,4-tetrahydroquinoline and 2-methylindoline by (S)-naproxen acyl chloride resulted in their kinetic resolution with the predominant formation of (S,S)-diastereoisomeric amides (de 78–76%), recrystallisation of which followed by acid hydrolysis gave individual (S)-isomers of heterocyclic amines????
\\\\expert2\\nbo\\Mendeleev Communications\\2002, v.12, N 1. p.27.pdf
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18.

Вид документа : Статья из журнала
Шифр издания : 54/K 46
Автор(ы) : Levit G. L., Krasnov V. P., Demin A. M., Kodess M. I., Sadretdinova L. Sh., Matveeva T. V., Ol'shevskaya V. A., Kalinin V. N., Chupakhin O. N., Charushin V. N.
Заглавие : Kinetic resolution of 1-methyl- and 1-phenyl-3-amino-1,2-dicarba-closo-dodecaboranes via acylation with chiral acyl chlorides [Electronic resource]
Место публикации : Mendeleev Communications. - 2004. - Vol. 14, № 6. - С. 293-295
Систем. требования: http://www.sciencedirect.com/science/article/pii/S0959943604704150
Примечания : 11.10.2011
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: A study of the kinetic resolution of racemic 1-substituted 3-amino-1,2-dicarba-closo-dodecaboranes by chiral acyl chlorides has shown that N-tosyl-(S)-prolyl and N-phthaloyl-(S)-alaninyl chlorides are more efficient resolving agents than (S)-naproxen chloride.
\\\\Expert2\\nbo\\Mendeleev Communications\\2004, v.14, p.293.pdf
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19.

Вид документа : Статья из журнала
Шифр издания : 54/K 46
Автор(ы) : Krasnov V. P., Levit G. L., Koroleva M. A., Bukrina I. M., Sadretdinova L. Sh., Andreeva I.N., Charushin V. N., Chupakhin O. N.
Заглавие : Kinetic resolution of heterocyclic amines by reaction with optically active acid chlorides. The effect of reaction conditions on the diastereoselectivity of acylation of (±)-3-methyl-2,3-dihydro-4H-1,4-benzoxazine [Electronic resource]
Место публикации : Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2004. - Vol. 53, № 6. - С. 1253-1256
Систем. требования: http://www.springerlink.com/content/r4732rtu8517k4p2/fulltext.pdf
Примечания : 24.10.2011
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: The influence of the reaction conditions (solvent, base) on the diastereoselectivity of acylation of (±)-3-methyl-2,3-dihydro-4H-1,4-benzoxazine with (S)-naproxen and N-tosyl-(S)-proline chlorides was studied. The highest diastereoselectivity was observed for the reaction carried out in benzene in the presence of aliphatic tertiary amines
\\\\Expert2\\nbo\\Russian Chemical Bulletin\\2004, 53 (6), 1253.pdf
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20.

Вид документа : Статья из журнала
Шифр издания : Г/K 46
Автор(ы) : Chulakov E. N., Korolyova M. A., Sadretdinova L. S., Tumashov A. A., Kodess M. I., Levit G. L., Krasnov V. P.
Заглавие : Kinetic resolution of racemic 6-substituted 1,2,3,4-tetrahydroquinaldines with chiral acyl chlorides. Experiment and quantum chemical simulation
Место публикации : Russian chemical bulletin. - 2021. - Vol. 70, № 5. - С. 890-899
ББК : Г
Предметные 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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