F 70 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] / E. V. Nosova, G. N. Lipunova, A. A. Laeva, V. N. Charushin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2005. - Vol. 41, № 11. - P1671-1677. - Библиогр. : с. 1677 (22 назв.) 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 |
K 46 Kinetic resolution of 1-methyl- and 1-phenyl-3-amino-1,2-dicarba-closo-dodecaboranes via acylation with chiral acyl chlorides [Electronic resource] / G. L. Levit, V. P. Krasnov, A. M. Demin, M. I. Kodess, L. Sh. Sadretdinova, T. V. Matveeva, V. A. Ol'shevskaya, V. N. Kalinin, O. N. Chupakhin, V. N. Charushin // Mendeleev Communications. - 2004. - Vol. 14, № 6. - P293-295 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 |
N 10 N-Phthaloyl-(S)-alanyl chloride as a chiral resolving agent for the kinetic resolution of heterocyclic amines [Text] / V. P. Krasnov, G. L. Levit, M. I. Kodess, V. N. Charushin, O. N. Chupakhin // Tetrahedron: Asymmetry . - 2004. - Vol. 15, № 5. - P859-862 : ил. - Библиогр.: с. 862 (7 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): HETEROCYCLIC AMINES -- CHLORIDE -- KINETIC RESOLUTION Аннотация: Acylation of heterocyclic amines with N-phthaloyl-(S)-alanyl chloride under kinetic resolution conditions resulted in the predominant formation of (S,S)-amides. The diastereoselectivity of resolution depended heavily on the structure of the resolved amine.???? \\\\Expert2\\nbo\\Tetrahedron Asymmetry\\2004, v.15, p.859.pdf |
E 54 Enantiomers of 3-amino-1-methyl-1,2-dicarba-closo-dodecaborane [Text] / V. P. Krasnov, G. L. Levit, V. N. Charushin, M. I. Kodess, V. N. Kalinin, O. N. Chupakhin // Tetrahedron: Asymmetry . - 2002. - Vol. 13, № 16. - P1833-1835. - Bibliogr. : p. 1835 (6 ref.) 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 |
K 46 Kinetic resolution of (±)-2-methyl-1,2,3,4-tetrahydroquinoline and (±)-2-methylindoline [Electronic resource] / V. P. Krasnov, G. L. Levit, I. N. Andreeva, A. N. Grishakov, V. N. Charushin, O. N. Chupakhin // Mendeleev Communications. - 2002. - Vol. 12, № 1. - P27-28 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 |
K 46 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 [Text] / V. P. Krasnov, G. L. Levit, I. M. Bukrina, I. N. Andreeva, L. Sh. Sadretdinova, M. A. Koroleva, M. I. Kodess, V. N. Charushin, O. N. Chupakhin // Tetrahedron: Asymmetry . - 2003. - Vol. 14, № 14. - P1985-1988. - Bibliogr. : p. 1988 (6 ref.) 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 |
K 46 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] / V. P. Krasnov, G. L. Levit, M. A. Koroleva, I. M. Bukrina, L. Sh. Sadretdinova, I. N. Andreeva, V. N. Charushin, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2004. - Vol. 53, № 6. - P1253-1256 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 |
S 91 Substituent effect on the stereoselectivity of acylation of racemic heterocyclic amines with N-phthaloyl-3-aryl-(S)-alanyl chlorides [Text] / G. L. Levit, D. A. Gruzdev, V. P. Krasnov, E. N. Chulakov, L. Sh. Sadretdinova, M. A. Ezhikova, M. I. Kodess, V. N. Charushin // Tetrahedron: Asymmetry . - 2011. - Vol. 22, № 2. - P185-189. - Bibliogr. : p. 189 (17ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The acylative kinetic resolution of racemic 2-methyl-1,2,3,4-tetrahydroquinoline and 2,3-dihydro-3-methyl-4H-1,4-benzoxazine using acyl chlorides of N-phthaloyl-(S)-phenylalanine, N-phthaloyl-3-(4-nitrophenyl)-(S)-alanine and N-phthaloyl-O-methyl-(S)-tyrosine as chiral resolving agents has been carried out. It is shown that the effectiveness of an acylative kinetic resolution depends on the electronic effects of substituents in the phenyl fragment of the acylating agent and increases as the electron-donating properties of the para-substituent (OMe H NO2) in phenyl fragment of N-phthaloyl-3-aryl-(S)-alanyl chlorides increase; conducting the process at a reduced temperature also contributes to an enhancement of the kinetic resolution \\\\Expert2\\nbo\\Tetrahedron Asymmetry\\2011, v. 22, p.185.pdf |
A 10 A convenient method for the preparation of mono- and bis-substituted photochromic bis(benzothienyl)perfluorocyclopentenes via regioselective Friedel–Crafts acylation / N. S. Bogatishcheva, V. N. Yarovenko, K. S. Levchenko, O. I. Kobeleva, T. M. Valova, V. A. Barachevskii, M. I. Struchkova, P. S. Shmelin, M. M. Krayushkin, V. N. Charushin // Tetrahedron Letters. - 2012. - Vol.53, №44. - С. 5948-5951 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): 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 |
R 35 Regioselective C2-and C8-Acylation of 5,11-Dihydroindolo[3,2-b]carbazoles and the Synthesis of Their 2,8-Bis(quinoxalinyl) Derivatives [Electronic resource] / R. A. Irgashev, N. A. Kazin, G. A. Kim, G. L. Rusinov, V. N. Charushin // Synthesis-Stuttgart. - 2015. - Vol. 47, № 22. - С. 3561-3572. - Bibliogr. : p. 3572 (11 ref) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): 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. |
R 35 Regioselective C2- and C8-Acylation of 5,11-Dihydroindolo[3,2-b]carbazoles and the Synthesis of Their 2,8-Bis(quinoxalinyl) Derivatives [Electronic resource] / R. A. Irgashev, N. A. Kazin, G. A. Kim, G. L. Rusinov, V. N. Charushin // Synthesis (Germany). - 2015. - Vol. 47, № 22. - С. 3561-3572 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): 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. \\\\expert2\\nbo\\Synthesis\\2015, v. 47. N 22. p.3561-3572.pdf |
R 35 Regioselective C2- and C8-Acylation of 5,11-Dihydroindolo[3,2-b]carbazoles and the Synthesis of Their 2,8-Bis(quinoxalinyl) Derivatives [Electronic resource] / R. A. Irgashev, N. A. Kazin, G. A. Kim, G. L. Rusinov, V. N. Charushin // Synthesis (Germany). - 2015. - Vol.47, № 22. - С. 3561-3572. - Bibliogr. : p. Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): 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. |
A 10 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 [Electronic resource] / R. A. Irgashev, N. A. Kazin, G. A. Kim, G. L. Rusinov, V. N. Charushin // RSC Advances. - 2016. - Vol. 6, № 74. - С. 70106-70116 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): 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 |
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.) 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 |