Synthesis of (Z)-1-benzylidene-3-(1H-indol-1-yl)-1H-indene-2,2(3H)-dicarbonitriles via three-component reaction of 2-alkynylbenzaldehyde, malononitrile, and indole

被引:13
作者
Qiu, Guanyinsheng [1 ]
Ding, Qiuping [1 ]
Peng, Yiyuan [1 ]
Wu, Jie [2 ]
机构
[1] Jiangxi Normal Univ, Key Lab Green Chem Jiangxi Prov, Coll Chem & Chem Engn, Nanchang 330027, Peoples R China
[2] Fudan Univ, Dept Chem, Shanghai 200433, Peoples R China
基金
中国国家自然科学基金;
关键词
2-Alkynylbenzaldehyde; Malononitrile; Indole; Three-component reaction; MULTICOMPONENT REACTIONS; ASYMMETRIC-SYNTHESIS; CATALYZED REACTIONS; EFFICIENT ROUTE; LEWIS-ACID; INDENE; DISCOVERY; AMINES; BOND; CARBOANNULATION;
D O I
10.1016/j.tetlet.2010.06.065
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Three-component reaction of 2-alkynylbenzaldehyde, malononitrile, and indole under mild conditions is described, which generates the desired (Z)-1-benzylidene-3-(1H-indene-1-yl)-1H-indene-2,2(3H)-dicarbo-nitriles in moderate to good yields. This reaction proceeds smoothly with high selectivity The tandem condensation, nucleophilic addition, and 5-exo-cyclization may be involved in the process (c) 2010 Elsevier Ltd All rights reserved
引用
收藏
页码:4391 / 4394
页数:4
相关论文
共 57 条
[1]   ELECTROINITIATED COPOLYMERIZATION OF INDENE WITH BETA-METHOXYSTYRENE [J].
AKBULUT, U ;
KHURSHID, A ;
HACIOGLU, B ;
TOPPARE, L .
POLYMER, 1990, 31 (07) :1343-1346
[2]   AuBr3-catalyzed [4+2] benzannulation between an enynal unit and enol [J].
Asao, N ;
Aikawa, H ;
Yamamoto, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (24) :7458-7459
[3]   AuBr3- and Cu(OTf)2-catalyzed intramolecular [4+2] cycloaddition of tethered alkynyl and alkenyl enynones and enynals:: A new synthetic method for functionalized polycyclic hydrocarbons [J].
Asao, N ;
Sato, K ;
Menggenbateer ;
Yamamoto, Y .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (09) :3682-3685
[5]   Pd-assisted multicomponent synthesis of heterocycles [J].
Balme, G ;
Bossharth, E ;
Monteiro, N .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (21) :4101-4111
[6]  
Barberá J, 1998, ANGEW CHEM INT EDIT, V37, P296, DOI 10.1002/(SICI)1521-3773(19980216)37:3<296::AID-ANIE296>3.0.CO
[7]  
2-U
[8]  
BECKER CL, 1991, SYNLETT, P642
[9]   Discovery of chemical reactions through multidimensional screening [J].
Beeler, Aaron B. ;
Su, Shun ;
Singleton, Chris A. ;
Porco, John A., Jr. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (05) :1413-1419
[10]  
Bienaymé H, 2000, CHEM-EUR J, V6, P3321, DOI 10.1002/1521-3765(20000915)6:18<3321::AID-CHEM3321>3.0.CO