Sulfuric acid promoted condensation cyclization of 2-(2-(trimethylsilyl) ethynyl)anilines with arylaldehydes in alcoholic solvents: an efficient one-pot synthesis of 4-alkoxy-2-arylquinolines

被引:32
作者
Wang, Yong [1 ]
Peng, Changlan [1 ]
Liu, Lanying [1 ]
Zhao, Jiaji [1 ]
Su, Li [1 ]
Zhu, Qiang [1 ]
机构
[1] Chinese Acad Sci, Inst Biol Chem, Guangzhou Inst Biomed & Hlth, Guangzhou 510663, Guangdong, Peoples R China
关键词
INDIRECT FRIEDLANDER SYNTHESIS; SUBSTITUTED QUINOLINES; 2,4-DISUBSTITUTED QUINOLINES; OXIDATIVE CYCLIZATION; RECENT PROGRESS; IN-VITRO; DERIVATIVES; 2-ARYL-1,2,3,4-TETRAHYDRO-4-QUINOLONES; 2-ARYLQUINOLINE; ANTIBACTERIAL;
D O I
10.1016/j.tetlet.2009.02.206
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient method for the synthesis of 4-alkoxy-2-arylquinolines has been developed. The reaction proceeds smoothly by heating a mixture of easily accessible 2-(2-(trimethylsilyl) ethynyl)anilines and arylaldehydes in alcoholic solvents in the presence of sulfuric acid. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2261 / 2265
页数:5
相关论文
共 58 条
[51]   In vitro antifungal activity of new series of homoallylamines and related compounds with inhibitory properties of the synthesis of fungal cell wall polymers [J].
Vargas, LY ;
Castelli, MV ;
Kouznetsov, VV ;
Urbina, JM ;
López, SN ;
Sortino, M ;
Enriz, RD ;
Ribas, JC ;
Zacchino, S .
BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (07) :1531-1550
[52]   Hypervalent iodine oxidation of 2-aryl-1,2,3,4-tetrahydro-4-quinolones: An expedient route to naturally occurring 4-alkoxy-2-arylquinolines [J].
Varma, RS ;
Kumar, D .
TETRAHEDRON LETTERS, 1998, 39 (50) :9113-9116
[53]   Chemotherapy for falciparum malaria: The armoury, the problems and the prospects [J].
Winstanley, PA .
PARASITOLOGY TODAY, 2000, 16 (04) :146-153
[54]   Microwave-assisted one-pot synthesis of 2,4-disubstituted quinolines under solvent-free conditions [J].
Yadav, JS ;
Reddy, BVS ;
Rao, RS ;
Naveenkumar, V ;
Nagaiah, K .
SYNTHESIS-STUTTGART, 2003, (10) :1610-1614
[55]  
Yamashkin S.A., 2006, J. Heterocycl. Chem, V42, P701
[56]   Synthesis of substituted quinolines by electrophilic cyclization of N-(2-alkynyl)anilines [J].
Zhang, XX ;
Campo, MA ;
Yao, TL ;
Larock, RC .
ORGANIC LETTERS, 2005, 7 (05) :763-766
[57]   A facile synthesis of 2-methylquinolines via Pd-catalyzed aza-Wacker oxidative cyclization [J].
Zhang, Zuhui ;
Tan, Jiajing ;
Wang, Zhiyong .
ORGANIC LETTERS, 2008, 10 (02) :173-175
[58]   Ethynyl ketene-S,S-acetals:: The highly reactive electron-rich dienophiles and applications in the synthesis of 4-functionalized quinolines via a one-pot three-component reaction [J].
Zhao, Yu-Long ;
Zhang, Wei ;
Wang, Shuang ;
Liu, Qun .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (13) :4985-4988