Copper-Catalyzed Tandem Reactions of 1-(2-Iodoary)-2-yn-1-ones with Isocyanides for the Synthesis of 4-Oxo-indeno[1,2-b]pyrroles

被引:87
作者
Cai, Qian [1 ]
Zhou, Fengtao
Xu, Tianfeng
Fu, Liangbing
Ding, Ke
机构
[1] Chinese Acad Sci, Guangzhou Inst Biomed & Hlth, Key Lab Regenerat Biol, Guangzhou 510530, Guangdong, Peoples R China
关键词
ALPHA-METALATED ISOCYANIDES; ASYMMETRIC ALDOL REACTION; COUPLING REACTIONS; OLIGOSUBSTITUTED PYRROLES; CROSS-CYCLOADDITION; CARBONYL-COMPOUNDS; ISOCYANOACETATE; ALDEHYDES; COMPLEX; DERIVATIVES;
D O I
10.1021/ol102826f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel copper-catalyzed tandem reaction of 1-(2-iodoaryl)-2-yn-1-ones with isocyanides is described. The reaction is through a formal [3 + 2] cycloaddition/coupling tandem process and leads to efficient formation of 4-oxo-indeno[1,2-b]pyrroles.
引用
收藏
页码:340 / 343
页数:4
相关论文
共 33 条
[1]  
Azizian J, 2006, SYNTHESIS-STUTTGART, P765
[2]   Copper in cross-coupling reactions - The post-Ullmann chemistry [J].
Beletskaya, IP ;
Cheprakov, AV .
COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2337-2364
[3]   Copper(I)-catalyzed diastereoselective formation of oxazolines and N-sulfonyl-2-imidazolines [J].
Benito-Garagorri, David ;
Bocokic, Vladica ;
Kirchner, Karl .
TETRAHEDRON LETTERS, 2006, 47 (49) :8641-8644
[4]   N-arylimidazole synthesis by cross-cycloaddition of isocyanides using a novel catalytic system [J].
Bonin, Marc-Andre ;
Giguere, Denis ;
Roy, Rene .
TETRAHEDRON, 2007, 63 (23) :4912-4917
[5]   Novel agonists of 5HT(2C) receptors. Synthesis and biological evaluation of substituted 2-(indol-1-yl)-1-methylethylamines and 2-(indeno[1,2-b]pyrrol-1-yl)-1-methylethylamines. Improved therapeutics for obsessive compulsive disorder [J].
Bos, M ;
Jenck, F ;
Martin, JR ;
Moreau, JL ;
Sleight, AJ ;
Wichmann, J ;
Widmer, U .
JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (17) :2762-2769
[6]   Synthesis of Aza-Fused Polycyclic Quinolines through Copper-Catalyzed Cascade Reactions [J].
Cai, Qian ;
Li, Zhengqiu ;
Wei, Jiajia ;
Fu, Liangbin ;
Ha, Chengyong ;
Pei, Duanqing ;
Ding, Ke .
ORGANIC LETTERS, 2010, 12 (07) :1500-1503
[7]   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
[8]  
Chatterjie N., 1975, TETRAHEDRON LETT, V30, P2535
[9]   Recent developments in isocyanide based multicomponent reactions in applied chemistry [J].
Dömling, A .
CHEMICAL REVIEWS, 2006, 106 (01) :17-89
[10]  
Dömling A, 2000, ANGEW CHEM INT EDIT, V39, P3168, DOI 10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO