Synthesis of enantiomers of 6-nitro- and 6-amino-2-methyl-1,2,3,4-tetrahydroquinolines

被引：14

作者：

Gruzdev, D. A. ^{[1
]}

Levit, G. L. ^{[1
]}

Kodess, M. I. ^{[1
]}

Krasnov, V. P. ^{[1
]}

机构：

[1] Russian Acad Sci, Ural Branch, I Ya Postovskii Inst Organ Synth, Ekaterinburg 620990, Russia

来源：

CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2012年 / 48卷 / 05期

基金：

俄罗斯基础研究基金会;

关键词：

amides; diastereoisomers; enantiomers; kinetic resolution; nitration; reduction; NONENZYMATIC KINETIC RESOLUTION; HETEROCYCLIC AMINES; CHLORIDES; (+/-)-2-METHYL-1,2,3,4-TETRAHYDROQUINOLINE; (+/-)-2-METHYLINDOLINE;

D O I：

10.1007/s10593-012-1053-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantiomers of 2-methyl-6-nitro-1,2,3,4-tetrahydroquinoline have been obtained by kinetic resolution of racemic 2-methyl-1,2,3,4-tetrahydroquinoline in acylation with acyl chlorides of N-protected amino acids followed by regioselective nitration of the diastereoisomeric amides and acidic hydrolysis. The introduction of a trifluoroacetyl protecting group into the position 1 of the enantio pure nitro compound followed by the reduction led to (S)-6-amino-2-methyl-1-trifluoroacetyl-1,2,3,4-tetra-hydroquinoline in a high yield.

引用

页码：748 / 757

页数：10

共 34 条

[11] Pharmacokinetics and pharmacodynamics of nonsteroidal androgen receptor ligands [J].

Gao, Wenqing ;

Kim, Juhyun ;

Dalton, James T. .

PHARMACEUTICAL RESEARCH, 2006, 23 (08) :1641-1658

[12] Iridium-Catalyzed Asymmetric Hydrogenation of Quinoline Derivatives with C3*-TunePhos [J].

Gou, Fa-Rong ;

Li, Wei ;

Zhang, Xumu ;

Liang, Yong-Min .

ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (14-15) :2441-2444

[13] Acylative kinetic resolution of racemic amines using N-phthaloyl-(S)-amino acyl chlorides [J].

Gruzdev, Dmitry A. ;

Levit, Galina L. ;

Krasnov, Victor P. ;

Chulakov, Evgeny N. ;

Sadretdinova, Liliya Sh. ;

Grishakov, Aleksandr N. ;

Ezhikova, Marina A. ;

Kodess, Mikhail I. ;

Charushin, Valery N. .

TETRAHEDRON-ASYMMETRY, 2010, 21 (08) :936-942

[14] Bone anabolic effects of S-40503, a novel nonsteroidal selective androgen receptor modulator (SARM), in rat models of osteoporosis [J].

Hanada, K ;

Furuya, K ;

Yamamoto, N ;

Nejishima, H ;

Ichikawa, K ;

Nakamura, T ;

Miyakawa, M ;

Amano, S ;

Sumita, Y ;

Oguro, N .

BIOLOGICAL & PHARMACEUTICAL BULLETIN, 2003, 26 (11) :1563-1569

[15]

Hoffman L., 1883, CHEM BER, V16, P727

[16]

Kagan H. B., 1998, TOPICS STEREOCHEMIST, V18, P249

[17] Nonenzymatic Acylative Kinetic Resolution of Racemic Amines and Related Compounds [J].

Krasnov, Victor P. ;

Gruzdev, Dmitry A. ;

Levit, Galina L. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (08) :1471-1493

[18] 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 [J].

Krasnov, VP ;

Levit, GL ;

Korolyova, MA ;

Bukrina, IM ;

Sadretdinova, LS ;

Andreeva, IN ;

Charushin, VN ;

Chupakhin, ON .

RUSSIAN CHEMICAL BULLETIN, 2004, 53 (06) :1253-1256

[19] N-phthaloyl-(S)-alanyl chloride as a chiral resolving agent for the kinetic resolution of heterocyclic amines [J].

Krasnov, VP ;

Levit, GL ;

Kodess, MI ;

Charushin, VN ;

Chupakhin, ON .

TETRAHEDRON-ASYMMETRY, 2004, 15 (05) :859-862

[20] 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 [J].

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

← 1 2 3 4 →