Lewis acidic ionic liquids for the synthesis of electrophilic alkenes via the Knoevenagel condensation

被引：238

作者：

Harjani, JR ^{[1
]}

Nara, SJ ^{[1
]}

Salunkhe, MM ^{[1
]}

机构：

[1] Inst Sci, Dept Chem, Bombay 400032, Maharashtra, India

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 06期

关键词：

D O I：

10.1016/S0040-4039(01)02341-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1-Butyl-3-methylimidazolium chloroaluminate. [bmim](ClAlCl3)-Al-., N=0.67 and 1-butylpyridinium chloroaluminate, [bpy](ClAlCl3)-Al-., N=0.67 ionic liquids were found to work well as the Lewis acid catalyst an solvent in the Knoevenagel condensations of benzaldehyde and substituted benzaldehydes with diethyl malonate to give benzylidene malonates. The benzylidene malonates subsequently underwent Michael additions with diethyl malonate. The extent of Michael product formed during the reaction was found to vary with the Lewis acidity and the molar proportion of ionic liquid. The influence of Lewis acidity of the ionic liquid on the Knoevenagel and Michael products is demonstrated. In the case of 2-hydroxyarylaldehydes, the reactions led to the formation of 3-ethoxycarbonyl coumarins under ambient conditions. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：1127 / 1130

页数：4

共 10 条

[1]

Bergmann E.D., 1959, ORG REACTIONS, V10, P179

[2] Montmorillonite KSF as an inorganic, water stable, and reusable catalyst for the knoevenagel synthesis of coumarin-3-carboxylic acids [J].

Bigi, F ;

Chesini, L ;

Maggi, R ;

Sartori, G .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (03) :1033-1035

[3] SYNTHESIS OF STEROIDAL 16,17-FUSED UNSATURATED DELTA-LACTONES [J].

GREEN, B ;

CRANE, RI ;

KHAIDEM, IS ;

LEIGHTON, RS ;

NEWAZ, SS ;

SMYSER, TE .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (05) :640-644

[4] Fries rearrangement in ionic melts [J].

Harjani, JR ;

Nara, SJ ;

Salunkhe, MM .

TETRAHEDRON LETTERS, 2001, 42 (10) :1979-1981

[5]

Jones G., 1967, ORGANICREACTIONS, V15, P204, DOI [DOI 10.1002/0471264180.OR015.02, 10.1002/0471264180.or015.02]

[6] Friedel-Crafts sulfonylation in 1-butyl-3-methylimidazolium chloroaluminate ionic liquids [J].

Nara, SJ ;

Harjani, JR ;

Salunkhe, MM .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (25) :8616-8620

[7]

RAO PS, 1991, TETRAHEDRON LETT, V32, P5821

[8]

Wasserscheid P, 2000, ANGEW CHEM INT EDIT, V39, P3772, DOI 10.1002/1521-3773(20001103)39:21<3772::AID-ANIE3772>3.0.CO

[9]

2-5

[10] Room-temperature ionic liquids. Solvents for synthesis and catalysis [J].

Welton, T .

CHEMICAL REVIEWS, 1999, 99 (08) :2071-2083

← 1 →