Ruthenium-catalyzed synthesis of quinolines from anilines and allylammonium chlorides in an aqueous medium via amine exchange reaction

被引:97
作者
Cho, CS
Kim, JS
Oh, BH
Kim, TJ
Shim, SC [1 ]
Yoon, NS
机构
[1] Kyungpook Natl Univ, Coll Engn, Dept Ind Chem, Taegu 702701, South Korea
[2] Kyungpook Natl Univ, Coll Engn, Dept Dyeing & Finishing, Taegu 702701, South Korea
关键词
ruthenium; catalyst; cyclization; quinolines; aqueous medium;
D O I
10.1016/S0040-4020(00)00694-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Anilines react with allylammonium chlorides in an aqueous medium (H2O-dioxane) in the presence of a catalytic amount of RuCl2(PPh3)(3) together with SnCl2. 2H(2)O to give the corresponding quinolines in moderate to good yields. The existence of SnCl2. 2H(2)O is necessary for the effective formation of quinolines, and a reaction pathway involving amine exchange reaction between anilines and allylammonium chlorides to form an imine is proposed for this catalytic process. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:7747 / 7750
页数:4
相关论文
共 36 条
[1]  
Arcadi A, 1998, SYNLETT, P446
[2]   RHODIUM AND MOLYBDENUM COMPLEXES AS CATALYSTS FOR CONVERSION OF NITROBENZENE AND ALIPHATIC-ALCOHOLS TO ALKYLQUINOLINES [J].
BOYLE, WJ ;
MARES, F .
ORGANOMETALLICS, 1982, 1 (07) :1003-1006
[3]  
Cacchi S, 1999, SYNLETT, P401
[4]   Ruthenium-catalysed synthesis of indoles from anilines and trialkanolamines in the presence of tin(II) chloride dihydrate [J].
Cho, CS ;
Lim, HK ;
Shim, SC ;
Kim, TJ ;
Choi, HJ .
CHEMICAL COMMUNICATIONS, 1998, (09) :995-996
[5]   Ruthenium-catalyzed synthesis of indoles from anilines and trialkanolammonium chlorides in an aqueous medium [J].
Cho, CS ;
Kim, JH ;
Shim, SC .
TETRAHEDRON LETTERS, 2000, 41 (11) :1811-1814
[6]   Synthesis of quinolines by ruthenium-catalyzed heteroannulation of anilines with 3-amino-1-propanol [J].
Cho, CS ;
Oh, BH ;
Shim, SC .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1999, 36 (05) :1175-1178
[7]   Ruthenium-catalyzed synthesis of 2-ethyl-3-methylquinolines from anilines and triallylamine [J].
Cho, CS ;
Oh, BH ;
Shim, SC .
TETRAHEDRON LETTERS, 1999, 40 (08) :1499-1500
[8]  
CHO CS, 2000, IN PRESS J HETEROCYC
[9]   PALLADIUM-CATALYZED SYNTHESIS OF 2-QUINOLONE DERIVATIVES FROM 2-IODOANILINES [J].
CORTESE, NA ;
ZIEGLER, CB ;
HRNJEZ, BJ ;
HECK, RF .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (15) :2952-2958
[10]   REACTIONS OF ANILINE WITH OLEFINS CATALYZED BY GROUP 8 METAL-COMPLEXES - N-ALKYLATION AND HETEROCYCLE FORMATION [J].
DIAMOND, SE ;
SZALKIEWICZ, A ;
MARES, F .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (02) :490-491