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

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