Ring opening reactions of quinoline substituted epoxides

被引：10

作者：

Boa, AN ^{[1
]}

Clark, S ^{[1
]}

Hirst, PR ^{[1
]}

Westwood, R ^{[1
]}

机构：

[1] Univ Hull, Dept Chem, Kingston Upon Hull HU6 7RX, N Humberside, England

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 52期

基金：

英国工程与自然科学研究理事会;

关键词：

regioselective; epoxide; amino alcohol; atropisomers;

D O I：

10.1016/j.tetlet.2003.10.062

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

6-Oxiranyl- and 3-oxiranyl-2-phenylquinoline-4-carboxylic acid diisopropylamides react with secondary amines and lithium amides to give (aminohydroxyethyl)quinolines but with opposite regioselectivities. Upon epoxidation of 3-formylquinoline 2 a similar to5:1 mixture of atropisomers is formed. This ratio is maintained upon epoxide ring-opening with amines in ethanol at reflux, but with lithium amides at room temperature a 1.3:1 ratio of isomers is obtained. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：9299 / 9302

页数：4

共 11 条

[1] Inhibitors of dihydroorotate dehydrogenase [J].

Batt, DG .

EXPERT OPINION ON THERAPEUTIC PATENTS, 1999, 9 (01) :41-54

[2]

BOA AN, UNPUB

[3] REGIOALTERNATING SELECTIVITY IN THE METAL SALT CATALYZED AMINOLYSIS OF STYRENE OXIDE [J].

CHINI, M ;

CROTTI, P ;

MACCHIA, F .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (20) :5939-5942

[4] Atroposelective attack of nucleophiles on 2-formyl-1-naphthamides and their derivatives: chelation and non-chelation control [J].

Clayden, J ;

McCarthy, C ;

Westlund, N ;

Frampton, CS .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (09) :1363-1378

[5] Atroposelective attack of nucleophiles and electrophiles on 2-acyl-1-naphthamides and their enolates [J].

Clayden, J ;

Westlund, N ;

Beddoes, RL ;

Helliwell, M .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (09) :1351-1361

[6]

DEXTER DL, 1985, CANCER RES, V45, P5563

[7] ORTEP-3 for Windows - a version of ORTEP-III with a Graphical User Interface (GUI) [J].

Journal of Applied Crystallography, 1997, 30 (pt 5)

[8] BORANES IN SYNTHESIS .6. A NEW SYNTHESIS OF BETA-AMINO ALCOHOLS FROM EPOXIDES - USE OF LITHIUM AMIDES AND AMINOBORANE CATALYSTS TO SYNTHESIZE BETA-AMINO ALCOHOLS FROM TERMINAL AND INTERNAL EPOXIDES IN HIGH-YIELD [J].

HARRIS, CE ;

FISHER, GB ;

BEARDSLEY, D ;

LEE, L ;

GORALSKI, CT ;

NICHOLSON, LW ;

SINGARAM, B .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (25) :7746-7751

[9] THE REACTION OF BENZYL HALIDES WITH THE SODIUM SALT OF 2-NITROPROPANE - A GENERAL SYNTHESIS OF SUBSTITUTED BENZALDEHYDES [J].

HASS, HB ;

BENDER, ML .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1949, 71 (05) :1767-1769

[10] PYRIMIDINE NUCLEOTIDE BIOSYNTHESIS IN ANIMALS - GENES, ENZYMES, AND REGULATION OF UMP BIOSYNTHESIS [J].

JONES, ME .

ANNUAL REVIEW OF BIOCHEMISTRY, 1980, 49 :253-279

← 1 2 →