Improved yields of meta-amination and symmetrical and unsymmetrical diamination of benzenes

被引:15
作者
Brown, GR [1 ]
Foubister, AJ [1 ]
Roberts, CA [1 ]
Wells, SL [1 ]
Wood, R [1 ]
机构
[1] AstraZeneca, Macclesfield SK10 4TG, Cheshire, England
关键词
amination; aryl halides; substituent effects;
D O I
10.1016/S0040-4039(01)00582-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Much higher yields were found after shorter reaction times for the meta-substituted amination of benzenes in DMPU with microwave heating in a sealed tube (180 degreesC. 5 h). e.g. piperidine and m-fluorobenzonitrile 1 gave the m-substituted 3 in 92% yield. These modified reaction conditions also afforded a new synthesis of unsymmetrical diamines in > 80% yield. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3917 / 3919
页数:3
相关论文
共 6 条
[1]   Palladium-catalyzed amination of aryl dibromides with secondary amines: synthetic and mechanistic aspects [J].
Beletskaya, IP ;
Bessmertnykh, AG ;
Guilard, R .
TETRAHEDRON LETTERS, 1999, 40 (35) :6393-6397
[2]   Synthesis of meta-substituted aniline derivatives by nucleophilic substitution [J].
Belfield, AJ ;
Brown, GR ;
Foubister, AJ ;
Ratcliffe, PD .
TETRAHEDRON, 1999, 55 (46) :13285-13300
[3]   Synthesis of meta-substituted aniline derivatives by nucleophilic substitution (vol 55, pg 13285, 1999) [J].
Belfield, AJ ;
Brown, GR ;
Foubister, AJ ;
Ratcliffe, PD .
TETRAHEDRON, 2000, 56 (24) :4107-4107
[4]   Recent synthetic advances in the nucleophilic amination of benzenes [J].
Belfield, AJ ;
Brown, GR ;
Foubister, AJ .
TETRAHEDRON, 1999, 55 (38) :11399-11428
[5]   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
[6]   Aromatic nucleophilic substitutions under microwave irradiation [J].
Salmoria, GV ;
Dall'Oglio, E ;
Zucco, C .
TETRAHEDRON LETTERS, 1998, 39 (17) :2471-2474