Aqueous Extract of Acacia concinna Pods: An Efficient Surfactant Type Catalyst for Synthesis of 3-Carboxycoumarins and Cinnamic Acids via Knoevenagel Condensation

被引:58
作者
Chavan, Hemant V. [1 ]
Bandgar, Babasaheb P. [1 ]
机构
[1] Solapur Univ, Sch Chem Sci, Med Chem Res Lab, Solapur 413255, Maharashtra, India
来源
ACS SUSTAINABLE CHEMISTRY & ENGINEERING | 2013年 / 1卷 / 08期
关键词
Green protocol; Acacia concinna; 3-Carboxycoumarins; Cinnamic acids; Knoevenagel condensation; Surfactant; CANCER-CELL INVASION; MELDRUMS ACID; ONE-POT; COUMARIN-3-CARBOXYLIC ACIDS; ASYMMETRIC REDUCTION; CAFFEIC ACID; IN-VITRO; DERIVATIVES; WATER; BIOTRANSFORMATION;
D O I
10.1021/sc4000237
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A simple, efficient, and environmentally benign protocol for the synthesis of 3-carboxycoumarins and cinnamic acids via Knoevenagel condensation has been achieved using aqueous extract of Acacia concinna pods as a naturally occurring surfactant type catalyst. We found for the first time that the aqueous extract of Acacia concinna pods could effectively catalyze the condensation of Meldrum's acid with salicyaldehyde/aromatic aldehyde to yield 3-carboxycoumarins and cinnamic acids in excellent yields under mild conditions. The low cost, easy availability of the catalyst, and simple reaction conditions suggest the possible use of the present method for large scale preparations.
引用
收藏
页码:929 / 936
页数:8
相关论文
共 55 条
[1]   Insulin-releasing properties of a series of cinnamic acid derivatives in vitro and in vivo [J].
Adisakwattana, Sirichai ;
Moonsan, Preecha ;
Yibchok-Anun, Sirintorn .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2008, 56 (17) :7838-7844
[2]  
Alfermann A., 1985, BIOCATALYSIS ORGANIC, P25
[3]   SAPOGENINS OF ACACIA CONCINNA .3. STRUCTURE OF ACACIGENIN-B, A NOVEL TRITERPENE ESTER ISOLATED FROM ACACIA-CONCINNA [J].
ANJANEYULU, ASR ;
BAPUJI, M ;
ROW, LR ;
SREE, A .
PHYTOCHEMISTRY, 1979, 18 (03) :463-466
[4]  
[Anonymous], KNOEVENAGEL REACT
[5]  
[Anonymous], KIRK OTHMER ENCY CHE
[6]  
[Anonymous], KIRK OTHMER ENCY CHE
[7]   Preparative synthesis of chiral alcohols by enantioselective reduction with Daucus carota root as biocatalyst [J].
Baldassarre, F ;
Bertoni, G ;
Chiappe, C ;
Marioni, F .
JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2000, 11 (01) :55-58
[8]   Uncatalyzed Knoevenagel condensation in PEG-600 at room temperature [J].
Bandgar, Babasaheb P. ;
Korbad, Balaji L. ;
Patil, Sachin A. ;
Bandgar, Sunita B. ;
Chavan, Hemant V. ;
Hote, Baliram S. .
AUSTRALIAN JOURNAL OF CHEMISTRY, 2008, 61 (09) :700-703
[9]   Solvent-free one-pot rapid synthesis of 3-carboxycoumarins using focused microwaves [J].
Bandgar, BP ;
Uppalla, LS ;
Kurule, DS .
GREEN CHEMISTRY, 1999, 1 (05) :243-245
[10]   Highly stereoselective reduction of 4-Aryl-2-oxo but-3-enoic carboxylic esters by plant cell culture of Daucus carota [J].
Baskar, B ;
Ganesh, S ;
Lokeswari, TS ;
Chadha, A .
JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2004, 27 (01) :13-17