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1.

Вид документа : Статья из журнала
Шифр издания :
Автор(ы) : Gruzdev D.A., Telegina A. A., Levit G. L., Krasnov V. P.
Заглавие : N-aminoacyl-3-amino-nido-carboranes as a group of boron-containing derivatives of natural amino acids
Место публикации : Journal of Organic Chemistry. - 2022. - Vol. 87, № 8. - С. 5437-5441
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: A new group of nido-carboranyl derivatives of natural (S)-amino acids containing from 9 to 18 boron atoms was obtained in good yields as a result of acylation of 3-amino-1,2-dicarba-closo-dodecaborane followed by deboronation. The proposed approach is convenient and based on the use of readily available reagents and is suitable for the synthesis of enantiopure nido-carboranyl derivatives of amino acids with various side chains, including water-soluble boron-containing amino acids (17 examples).
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2.

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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3.

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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4.

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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5.

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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6.

Вид документа : Статья из журнала
Шифр издания : 54/R 35
Автор(ы) : Irgashev R. A., Kazin N. A., Kim G. A., Rusinov G. L., Charushin V. N.
Заглавие : Regioselective C2-and C8-Acylation of 5,11-Dihydroindolo[3,2-b]carbazoles and the Synthesis of Their 2,8-Bis(quinoxalinyl) Derivatives [Электронный ресурс]
Место публикации : Synthesis-Stuttgart. - 2015. - Vol. 47, № 22. - С. 3561-3572
Систем. требования: http://apps.webofknowledge.com/
Примечания : Bibliogr. : p. 3572 (11 ref). - 18.01.16
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Ключевые слова (''Своб.индексиров.''): 5,11-dihydroindolo[3,2-b]carbazoles --2-arylgly-oxals--acylation
Аннотация: An efficient approach for the double acetylation of 5,11-dihexyl- 6,12-di(hetero) aryl-substituted 5,11-dihydroindolo[3,2-b] carbazoles with acetic anhydride in the presence of boron trifluoride etherate has been developed, thus affording the corresponding 2,8-diacetyl derivatives in good yields. A similar acylation has been shown to occur by the reaction of anhydrides of other carboxylic acids. Oxidation of the obtained 2,8-diacetyl derivatives with selenium dioxide takes place on heating or under microwave irradiation, thus resulting in the formation of the corresponding 2,8-diglyoxals. The latter proved to react with aromatic o-diamines to afford new indolo[3,2-b] carbazoles bearing quinoxalinyl fragments at C-2 and C-8. Major optical properties of quinoxaline- containing indolo[3,2-b] carbazoles have been measured.
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7.

Вид документа : Статья из журнала
Шифр издания : 54/R 35
Автор(ы) : Irgashev R. A., Kazin N. A., Kim G. A., Rusinov G. L., Charushin V. N.
Заглавие : Regioselective C2- and C8-Acylation of 5,11-Dihydroindolo[3,2-b]carbazoles and the Synthesis of Their 2,8-Bis(quinoxalinyl) Derivatives
Место публикации : Synthesis (Germany). - 2015. - Vol. 47, № 22. - С. 3561-3572
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Ключевые слова (''Своб.индексиров.''): 5,11-dihydroindolo[3,2-b]carbazoles--acylation-- 2-arylglyoxals
Аннотация: An efficient approach for the double acetylation of 5,11-dihexyl-6,12-di(hetero)aryl-substituted 5,11-dihydroindolo[3,2-b]carbazoles with acetic anhydride in the presence of boron trifluoride etherate has been developed, thus affording the corresponding 2,8-diacetyl derivatives in good yields. A similar acylation has been shown to occur by the reaction of anhydrides of other carboxylic acids. Oxidation of the obtained 2,8-diacetyl derivatives with selenium dioxide takes place on heating or under microwave irradiation, thus resulting in the formation of the corresponding 2,8-diglyoxals. The latter proved to react with aromatic o-diamines to afford new indolo[3,2-b]carbazoles bearing quinoxalinyl fragments at C-2 and C-8. Major optical properties of quinoxaline-containing indolo[3,2-b]carbazoles have been measured.
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8.

Вид документа : Статья из журнала
Шифр издания : 54/R 35
Автор(ы) : Irgashev R. A., Kazin N. A., Kim G. A., Rusinov G. L., Charushin V. N.
Заглавие : Regioselective C2- and C8-Acylation of 5,11-Dihydroindolo[3,2-b]carbazoles and the Synthesis of Their 2,8-Bis(quinoxalinyl) Derivatives [Электронный ресурс]
Место публикации : Synthesis (Germany). - 2015. - Vol.47, № 22. - С. 3561-3572
Систем. требования: https://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-0035-1560183
Примечания : Bibliogr. : p. . - 29.03.16
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Ключевые слова (''Своб.индексиров.''): acylation--type heteroacenes--quinoxalines
Аннотация: An efficient approach for the double acetylation of 5,11-dihexyl-6,12-di(hetero)aryl-substituted 5,11-dihydroindolo[3,2-b]carbazoles with acetic anhydride in the presence of boron trifluoride etherate has been developed, thus affording the corresponding 2,8-diacetyl derivatives in good yields. A similar acylation has been shown to occur by the reaction of anhydrides of other carboxylic acids. Oxidation of the obtained 2,8-diacetyl derivatives with selenium dioxide takes place on heating or under microwave irradiation, thus resulting in the formation of the corresponding 2,8-diglyoxals. The latter proved to react with aromatic o-diamines to afford new indolo[3,2-b]carbazoles bearing quinoxalinyl fragments at C-2 and C-8. Major optical properties of quinoxaline-containing indolo[3,2-b]carbazoles have been measured.
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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/N 89
Автор(ы) : Shcherbakov K. V., Bazhin D. N., Burgart Ya. V., Saloutin V. I.
Заглавие : Novel 3-acetyl-2-methyl-polyfluorochromones in reactions with amines and esters of amino acids [Электронный ресурс]
Место публикации : Chemistry of Heterocyclic Compounds. - 2015. - Vol. 51, № 11/12. - С. 961-968
Систем. требования: http://link.springer.com/article/10.1007/s10593-016-1805-y
Примечания : Bibliogr. : p. 967-968 (21 ref.). - 03.02.2016
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Ключевые слова (''Своб.индексиров.''): amine --acylation--chromone
Аннотация: Novel 3-acetyl-2-methyl-polyfluoro-4Н-chromen-4-ones were obtained via one-pot acylation of acetylacetone with polyfluorobenzoyl chlorides. These chromones were shown to form N-substituted 3-amino-1-[2-hydroxy(polyfluoro)phenyl]but-2-en-1-ones in reaction with aliphatic primary amines, esters of amino acids, and aqueous ammonia via opening of the pyrone ring and deacylation
\\\\expert2\\nbo\\Chemistry of Heterocyclic Compounds\\2015, v.51, N 11-12, p. 961-968.pdf
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