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

被引：0

作者：

V. P. Krasnov

G. L. Levit

M. A. Korolyova

I. M. Bukrina

L. Sh. Sadretdinova

I. N. Andreeva

V. N. Charushin

O. N. Chupakhin

机构：

[1] Ural Branch of the Russian Academy of Sciences,I. Ya. Postovsky Institute of Organic Synthesis

来源：

Russian Chemical Bulletin | 2004年 / 53卷

关键词：

kinetic resolution of racemates; 3-methyl-2,3-dihydro-4; -1,4-benzoxazine; acid chlorides; (; )-naproxen; -tosyl-(; )-proline; acylation;

D O I：

暂无

中图分类号：

学科分类号：

摘要：

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.

引用

页码：1253 / 1256

页数：3

共 9 条

[1] 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
Krasnov, VP
Levit, GL
Korolyova, MA
Bukrina, IM
Sadretdinova, LS
Andreeva, IN
Charushin, VN
Chupakhin, ON
RUSSIAN CHEMICAL BULLETIN, 2004, 53 (06) : 1253 - 1256
[2] Kinetic resolution of (±)-2,3-dihydro-3-methyl-4H-1,4-benzoxazine in the reaction with (S)-naproxen chloride:: a theoretical study
Potemkin, VA
Krasnov, VP
Levit, GL
Bartashevich, EV
Andreeva, IN
Kuzminsky, MB
Anikin, NA
Charushin, VN
Chupakhin, ON
MENDELEEV COMMUNICATIONS, 2004, 14 (02) : 69 - 71
[3] 2-Arylpropionyl chlorides in kinetic resolution of racemic 3-methyl-2,3-dihydro-4H-[1,4]benzoxazines
E. N. Chulakov
D. A. Gruzdev
G. L. Levit
L. Sh. Sadretdinova
V. P. Krasnov
V. N. Charushin
Russian Chemical Bulletin, 2011, 60 : 948 - 954
[4] 2-Arylpropionyl chlorides in kinetic resolution of racemic 3-methyl-2,3-dihydro-4H-[1,4]benzoxazines
Chulakov, E. N.
Gruzdev, D. A.
Levit, G. L.
Sadretdinova, L. Sh
Krasnov, V. P.
Charushin, V. N.
RUSSIAN CHEMICAL BULLETIN, 2011, 60 (05) : 948 - 954
[5] Kinetic resolution of racemic 3-tert-butyl-3,4-dihydro-2H-[1,4]benzoxazine via acylation with chiral acyl chlorides
Vakarov, S. A.
Gruzdev, D. A.
Chulakov, E. N.
Levit, G. L.
Krasnov, V. P.
RUSSIAN CHEMICAL BULLETIN, 2019, 68 (04) : 841 - 847
[6] Kinetic resolution of racemic 3-tert-butyl-3,4-dihydro-2H-[1,4]benzoxazine via acylation with chiral acyl chlorides
S. A. Vakarov
D. A. Gruzdev
E. N. Chulakov
G. L. Levit
V. P. Krasnov
Russian Chemical Bulletin, 2019, 68 : 841 - 847
[7] 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
Krasnov, VP
Levit, GL
Bukrina, IM
Andreeva, IN
Sadretdinova, LS
Korolyova, MA
Kodess, MI
Charushin, VN
Chupakhin, ON
TETRAHEDRON-ASYMMETRY, 2003, 14 (14) : 1985 - 1988
[8] Five-membered 2,3-dioxoheterocycles:: LIX.: Reaction of 3-aroyl-1H-pyrrolo[2,1-c][1,4]benzoxazine-1,2,4-triones with acyclic β-enaminoesters.: Crystal and molecular structure of ethyl 3-benzoyl-4-hydroxy-1-o-hydroxyphenyl-5-oxo-2,3-dihydro-1H-pyrrolo-2-spiro-3′-(5-methyl-2-oxo-2,3-dihydro-1H-pyrrolo-4-carboxylate)
Racheva, N. L.
Aliev, Z. G.
Belova, M. A.
Mashevskaya, I. V.
Maslivets, A. N.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 44 (05) : 701 - 705
[9] Five-membered 2,3-Dioxoheterocycles: LIX. Reaction of 3-Aroyl-1H-pyrrolo[2,1-c][1,4]benzoxazine-1,2,4-triones with Acyclic β-Enaminoesters. Crystal and Molecular Structure of Ethyl 3-Benzoyl-4-hydroxy-1-o-hydroxyphenyl-5-oxo-2,3-dihydro-1H-pyrrolo-2-spiro-3′-(5-methyl-2-oxo-2,3-dihydro-1H-pyrrolo-4-carboxylate)
N. L. Racheva
Z. G. Aliev
M. A. Belova
I. V. Mashevskaya
A. N. Maslivets
Russian Journal of Organic Chemistry, 2008, 44 : 701 - 705

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