Uncatalyzed Condensation of Active Methylene Compounds with Aldehydes or Ketones in Aqueous Medium

被引:0
作者
Cheng, Qing-Fang [1 ,2 ]
Xu, Xing-You [1 ,2 ]
Ma, Wei-Xing [1 ]
Zhang, Hui [1 ]
Liu, Li-Sha [1 ]
Liu, Feng [1 ]
Yang, Xu-Jie [2 ]
机构
[1] Huaihai Inst Technol, Dept Chem Technol, Lianyungang 222005, Peoples R China
[2] Nanjing Univ Sci & Technol, Mat Chem Lab, Nanjing 210094, Peoples R China
关键词
condensation; carbonyl compound; active methylene compound; medium;
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Knoevenagel condensations of various carbonyl compounds with active methylene compounds were reported in water medium without adding any catalyst. The condensation of aromatic aldehydes with active methylene compounds like malononitrile, cyanoacetamide and ethyl cyanoacetate has been found to proceed very efficiently at room temperature giving excellent yields, but the condensation of heteroaromatic, alpha,beta-unsaturated and aliphatic aldehydes with active methylene compounds proceeded smoothly in 50 similar to 65 degrees C with good yields and the reactions of aromatic, aliphatic ketones as well as p-phthalaldehyde with malononitrile also proceeded in 75 similar to 85 degrees C with moderate yields. The work-up procedure is simple, efficient and environment-friendly.
引用
收藏
页码:1767 / 1771
页数:5
相关论文
共 21 条
[1]  
Ayoubi S. A. E., 1994, SYNTHESIS-STUTTGART, P258
[2]   Ammonium acetate-basic alumina catalyzed Knoevenagel condensation under microwave irradiation under solvent-free condition [J].
Balalaie, S ;
Nemati, N .
SYNTHETIC COMMUNICATIONS, 2000, 30 (05) :869-875
[3]  
Bian YJ, 2006, CHINESE J ORG CHEM, V26, P1165
[4]   Clean synthesis in water: uncatalysed preparation of ylidenemalononitriles [J].
Bigi, F ;
Conforti, ML ;
Maggi, R ;
Piccinno, A ;
Sartori, G .
GREEN CHEMISTRY, 2000, 2 (03) :101-103
[5]   Stereoselective intramolecular hetero Diels-Alder reactions of 1-oxa-1,3-butadienes:: synthesis of novel annelated pyrrolo[1,2-a]indoles [J].
Borah, HN ;
Deb, ML ;
Boruah, RC ;
Bhuyan, PJ .
TETRAHEDRON LETTERS, 2005, 46 (19) :3391-3393
[6]  
Brufola G, 1997, HETEROCYCLES, V45, P1715
[7]   Uncatalysed Knoevenagel condensation in aqueous medium at room temperature [J].
Deb, ML ;
Bhuyan, PJ .
TETRAHEDRON LETTERS, 2005, 46 (38) :6453-6456
[8]   Silica gel catalysed Knoevenagel condensation in Dry Media under microwave irradiation [J].
delaCruz, P ;
DiezBarra, E ;
Loupy, A ;
Langa, F .
TETRAHEDRON LETTERS, 1996, 37 (07) :1113-1116
[9]   PROPERTIES AND REACTIONS OF YLIDENEMALONONITRILES [J].
FREEMAN, F .
CHEMICAL REVIEWS, 1980, 80 (04) :329-350
[10]  
Jones G., 1967, ORGANICREACTIONS, V15, P204, DOI [DOI 10.1002/0471264180.OR015.02, 10.1002/0471264180.or015.02]