Synthesis of Aza-Fused Polycyclic Quinolines through Copper-Catalyzed Cascade Reactions

被引:76
作者
Cai, Qian [1 ,2 ,3 ]
Li, Zhengqiu [4 ]
Wei, Jiajia [1 ,2 ,3 ]
Fu, Liangbin [1 ,2 ,3 ]
Ha, Chengyong [4 ]
Pei, Duanqing [1 ,2 ,3 ]
Ding, Ke [1 ,2 ,3 ]
机构
[1] Chinese Acad Sci, Key Lab Regenerat Biol, Guangzhou Inst Biomed, Guangzhou 510530, Guangdong, Peoples R China
[2] Chinese Acad Sci, Inst Biol Chem, Guangzhou Inst Biomed, Guangzhou 510530, Guangdong, Peoples R China
[3] Chinese Acad Sci, Guangzhou Inst Hlth, Guangzhou 510530, Guangdong, Peoples R China
[4] Chinese Acad Sci, Key Lab Cellulose & Lignocellulos Chem, Guangzhou Inst Chem, Guangzhou 510530, Guangdong, Peoples R China
关键词
COUPLING REACTIONS; EFFICIENT SYNTHESIS; BOND FORMATION; C-N; DERIVATIVES; PHENANTHRENES; CYCLIZATIONS; HETEROARENES; HETEROCYCLES; CHEMISTRY;
D O I
10.1021/ol1002225
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new and efficient method for the synthesis of aza-fused polycyclic quinolines (e.g., benzimidazo[1,2-a]quinolines) is described. This protocol Includes an Intermolecular condensation followed by a copper-catalyzed Intramolecular C-N coupling reaction. The method is applied to a wide range of 2-iodo, 2-bromo, and 2-chloro aryl aldehyde substrates to yield the aza-fused polycyclic quinolines in good yields.
引用
收藏
页码:1500 / 1503
页数:4
相关论文
共 37 条
[1]   Fused quinolines. Recent synthetic approaches to azoloquinolines. A review [J].
Abass, M .
HETEROCYCLES, 2005, 65 (04) :901-965
[2]  
Balasubramanian M., 1996, COMPREHENSIVE HETERO, V5, P245, DOI 10.1016/B978-008096518-5.00109
[3]   Copper in cross-coupling reactions - The post-Ullmann chemistry [J].
Beletskaya, IP ;
Cheprakov, AV .
COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2337-2364
[4]   NEW BENZIMIDAZOLE SYNTHESIS [J].
BENINCORI, T ;
SANNICOLO, F .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1988, 25 (03) :1029-1033
[5]   Rapid access to oxindoles by the combined use of an Ugi four-component reaction and a microwave-assisted intramolecular Buchwald-Hartwig amidation reaction [J].
Bonnaterre, Florence ;
Bois-Choussy, Michele ;
Zhu, Jieping .
ORGANIC LETTERS, 2006, 8 (19) :4351-4354
[6]   Assembly of indole-2-carboxylic acid esters through a ligand-free copper-catalysed cascade process [J].
Cai, Qian ;
Li, Zhengqiu ;
Wei, Jiajia ;
Ha, Chengyong ;
Pei, Duanqing ;
Ding, Ke .
CHEMICAL COMMUNICATIONS, 2009, (48) :7581-7583
[7]   Tandem Pd-Catalyzed Double C-C Bond Formation: Effect of Water [J].
Chai, David I. ;
Lautens, Mark .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (08) :3054-3061
[8]   Present trends and future strategy in chemotherapy of malaria [J].
Chauhan, PMS ;
Srivastava, SK .
CURRENT MEDICINAL CHEMISTRY, 2001, 8 (13) :1535-1542
[9]   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
[10]  
COOPER G, 1975, J CHEM SOC P1, P75