Efficient nucleophilic substitution reactions of quinolyl and isoquinolyl halides with nucleophiles under focused microwave irradiation

被引:32
作者
Cherng, YJ [1 ]
机构
[1] Chung Tai Inst Hlth Sci & Technol, Dept Med Technol, Taichung 40605, Taiwan
关键词
nucleophilic substitution reaction;
D O I
10.1016/S0040-4020(01)01225-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Nucleophilic substitution reactions of 2-chloroquinoline, 3-bromoquinoline and 4-bromoisoquinoline with thiolate, alkoxy ions and aniline were completed within several minutes under microwave irradiation. This method gives the desired products with yields up to 99% in a short reaction time, and is superior to the classical heating process. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1125 / 1129
页数:5
相关论文
共 41 条
[21]   REACTIONS OF SOME AMINES WITH HETEROCYCLIC ETHERS [J].
GILMAN, H ;
ZAREMBER, I ;
BEEL, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (12) :3177-3179
[22]   THE REACTIONS OF THIOLS WITH SOME ALKYL AND ARYL HETEROCYCLIC ETHERS [J].
ILLUMINATI, G ;
GILMAN, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1949, 71 (10) :3349-3351
[24]   New solvent free organic synthesis using focused microwaves [J].
Loupy, A ;
Petit, A ;
Hamelin, J ;
Texier-Boullet, F ;
Jacquault, P ;
Mathé, D .
SYNTHESIS-STUTTGART, 1998, (09) :1213-1234
[25]   APPLICATIONS OF MICROWAVE-ACCELERATED ORGANIC-SYNTHESIS [J].
MAJETICH, G ;
HICKS, R .
RADIATION PHYSICS AND CHEMISTRY, 1995, 45 (04) :567-579
[26]   THE APPLICATIONS OF MICROWAVES IN CHEMICAL SYNTHESES [J].
MINGOS, DMP .
RESEARCH ON CHEMICAL INTERMEDIATES, 1994, 20 (01) :85-91
[27]   C=C-CONJUGATED CARBODIIMIDES AS 2-AZADIENES IN INTRAMOLECULAR [4 + 2] CYCLOADDITIONS - ONE-POT PREPARATION OF QUINOLINE, ALPHA-CARBOLINE, AND QUININDOLINE DERIVATIVES [J].
MOLINA, P ;
ALAJARIN, M ;
VIDAL, A ;
SANCHEZANDRADA, P .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (03) :929-939
[28]   PHOTOSTIMULATED REACTIONS OF 2-BROMOPYRIDINE AND 2-CHLOROQUINOLINE WITH NITRILE-STABILIZED CARBANIONS AND CERTAIN OTHER NUCLEOPHILES [J].
MOON, MP ;
KOMIN, AP ;
WOLFE, JF ;
MORRIS, GF .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (14) :2392-2399
[29]   Microwave-promoted transformations: Fast and chemoselective N-acylation of amino alcohols using catalytic amounts of dibutyltin oxide. Influence of the power output and the nature of the acylating agent on the selectivity [J].
Morcuende, A ;
Ors, M ;
Valverde, S ;
Herradon, B .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (16) :5264-5270
[30]  
PILAR MF, 2001, SYNLETT, V2, P218