Synthesis of meta-substituted aniline derivatives by nucleophilic substitution

被引：32

作者：

Belfield, AJ ^{[1
]}

Brown, GR ^{[1
]}

Foubister, AJ ^{[1
]}

Ratcliffe, PD ^{[1
]}

机构：

[1] AstraZeneca, Macclesfield SK10 4TG, Cheshire, England

来源：

TETRAHEDRON | 1999年 / 55卷 / 46期

关键词：

amination; aryl halides; substituent effects;

D O I：

10.1016/S0040-4020(99)00818-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Substitution by amines of fluorobenzenes containing a meta-substituted electron withdrawing group (EWG), in DMSO at 100 degrees C over 60 h gave meta-substituted aniline derivatives in isolated yields of up to 98%. The scope of the reaction is explored in terms of reaction conditions and substrates. It is postulated that facile meta-substitutions are facilitated through field stabilisation of the intermediate anion by EWG substituents. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：13285 / 13300

页数：16

共 18 条

[1]

BELFIELD AJ, 1999, IN PRESS TETRAHEDRON

[2] AROMATIC NUCLEOPHILIC REPLACEMENT .16. REACTIONS OF ORTHO-FLUORO-NITROBENZENE- AND PARA-FLUORO-NITROBENZENE AND 1-FLUORO-3,5-DINITROBENZENE WITH SULPHITE IONS, AND OF ORTHO FLUORONITROBENZENE AND PARA-FLUORONITROBENZENE WITH ISOPROPOXIDE IONS [J].

BEVAN, CWL ;

FOLEY, AJ ;

HIRST, J ;

UWAMU, WO .

JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1970, (05) :794-&

[3] SYNTHESIS OF SOME N-CARBOXYLIC ACID-DERIVATIVES OF 3-PHENOXYPYRROLIDINES, 4-PHENOXYPIPERIDINES, AND 3-PHENOXYNORTROPANES WITH MUSCLE RELAXANT AND ANTICONVULSANT ACTIVITIES [J].

BOSWELL, RF ;

HELSLEY, GC ;

DUNCAN, RL ;

FUNDERBURK, WH ;

JOHNSON, DN .

JOURNAL OF MEDICINAL CHEMISTRY, 1974, 17 (09) :1000-1008

[4] High yields of meta-substituted amination products in the SNAr substitution of benzenes [J].

Brown, GR ;

Foubister, AJ ;

Ratcliffe, PD .

TETRAHEDRON LETTERS, 1999, 40 (06) :1219-1222

[5] SYNTHESIS AND RESOLUTION OF 3-SUBSTITUTED MORPHOLINE APPETITE-SUPPRESSANTS AND CHIRAL SYNTHESIS VIA O-ARYLHOMOSERINES [J].

BROWN, GR ;

FOUBISTER, AJ ;

STRIBLING, D .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (03) :547-551

[6]

GLANKOWSKI EJ, 1985, J MED CHEM, V28, P66

[7]

GURAM AS, 1995, ANGEW CHEM INT EDIT, V34, P1348, DOI 10.1002/anie.199513481

[8]

Hansch C., 1995, Exploring QSAR-Fundamentals and Applications in Chemistry and Biology

[9]

Hartwig JF, 1998, ANGEW CHEM INT EDIT, V37, P2046, DOI 10.1002/(SICI)1521-3773(19980817)37:15<2046::AID-ANIE2046>3.0.CO

[10]

2-L

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