Facile one-pot synthesis of polysubstituted quinolines under solvent-free conditions using sulfamic acid as a reusable catalyst

被引:11
作者
Zhang, Min [1 ]
Xiong, Biao [1 ]
Yang, Wei [1 ]
Kumar, D. N. T. [1 ]
Ding, Yu-Qiang [1 ]
机构
[1] Jiangnan Univ, Sch Chem & Mat Engn, Wuxi 214122, Jiangsu, Peoples R China
来源
MONATSHEFTE FUR CHEMIE | 2012年 / 143卷 / 03期
关键词
Multicomponent reaction; Heterocylces; Reusable sulfamic acid catalyst; Solvent-free conditions; Eliminations and oxidations; SUBSTITUTED QUINOLINES; CONJUGATED POLYMERS; DERIVATIVES; INHIBITORS; CYCLIZATION; ALDEHYDES; PROFILES; ION;
D O I
10.1007/s00706-011-0590-7
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A facile one-pot synthesis of polysubstituted quinoline derivatives has been demonstrated by using sulfamic acid as a reusable catalyst under solvent-free conditions. The synthetic method provides the basis and advantages of a simple experimental procedure and easy recovery and reuse of catalyst, which makes it a highly practical and environmentally benign pathway for the synthesis of polysubstituted quinolines. Interestingly, this one-pot synthesis could produce the products regioselectively in the presence of dis-symmetrical arylamines.
引用
收藏
页码:471 / 478
页数:8
相关论文
共 34 条
[1]   Synthesis, potency, and in vivo profiles of quinoline containing histamine H3 receptor inverse agonists [J].
Altenbach, Robert J. ;
Liu, Huaqing ;
Banfor, Patricia N. ;
Brownian, Kaitlin E. ;
Fox, Gerard B. ;
Fryer, Ryan M. ;
Komater, Victoria A. ;
Krueger, Kathleen M. ;
Marsh, Kennan ;
Miller, Thomas R. ;
Pan, Jia Bao ;
Pan, Liping ;
Sun, Minghua ;
Thiffault, Christine ;
Wetter, Jill ;
Zhao, Chen ;
Zhou, Deliang ;
Esbenshade, Timothy A. ;
Hancock, Arthur A. ;
Cowart, Marlon D. .
JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (22) :5439-5448
[2]  
Beller M, 2000, CHEM-EUR J, V6, P2513, DOI 10.1002/1521-3765(20000717)6:14<2513::AID-CHEM2513>3.0.CO
[3]  
2-V
[4]   Synthesis of substituted quinolines from arylamines and aldehydes via tandem reaction promoted by chlorotrimethylsilane [J].
Bian, Xiaoqin ;
Liu, Lanhai ;
Geng, Xin ;
Xie, Zengyang ;
Li, Shuangshuang ;
Wang, Cunde .
JOURNAL OF CHEMICAL RESEARCH, 2009, (02) :81-83
[5]   Catalytic activity of iron(III), aluminum(III), cobalt(II), and magnesium(II) chloride crystal hydrates in the condensation of aniline with butyraldehyde [J].
Bulgakov, R. G. ;
Kuleshov, S. P. ;
Vafin, R. R. ;
Dzhemilev, U. M. .
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 45 (06) :944-945
[6]   Synthesis and antibacterial evaluation of certain quinolone derivatives [J].
Chen, YL ;
Fang, KC ;
Sheu, JY ;
Hsu, SL ;
Tzeng, CC .
JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (14) :2374-2377
[7]   Palladium catalysis in reductive alkyl group transfer from trialkylamines to nitroarenes followed by cyclization [J].
Cho, Chan Sik ;
Kim, Tae Gyun ;
Kim, Hae Won .
CATALYSIS COMMUNICATIONS, 2009, 10 (11) :1482-1485
[8]  
Combes A., 1888, B CHIM SOC FRANCE, V49, P89
[9]   Facile one-pot method for the synthesis of novel glycosylidene-based quinolines [J].
Dobbelaar, Peter H. ;
Marzabadi, Cecilia H. .
TETRAHEDRON LETTERS, 2010, 51 (01) :201-204
[10]  
Doebner, 1881, BER DTSCH CHEM GES, V14, P2812, DOI DOI 10.1002/CBER.188101402258