Greener synthesis of spirooxindole in deep eutectic solvent

被引：100

作者：

Azizi, Najmedin ^{[1
]}

Dezfooli, Sahar ^{[2
]}

Hashemi, Mohammad Mahmoudi ^{[3
]}

机构：

[1] Chem & Chem Engn Res Ctr Iran, Tehran, Iran

[2] Islamic Azad Univ, Sci & Res Branch, Young Researchers & Elites Club, Tehran, Iran

[3] Islamic Azad Univ, Dept Chem, Sci & Res Branch, Tehran, Iran

来源：

JOURNAL OF MOLECULAR LIQUIDS | 2014年 / 194卷

关键词：

Acenaphthoquinone; Cumarin; Green chemistry; Spirooxindole; Ionic liquid; lsatin; EFFICIENT SYNTHESIS; IONIC LIQUIDS; POTENT;

D O I：

10.1016/j.molliq.2014.01.009

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A simple and efficient synthesis of spirooxindole derivatives by one-pot, three-component reaction of isatins, malononitrile and different nucleophiles under catalyst-free condition in deep eutectic solvent is reported. A series of biological importance, spirooxindole derivatives were synthesized via a multicomponent reaction of isatin, or acenaphthoquinone, and malononitrile or cyanoacetic ester with 1,3-dicarbonyl compounds, naphtol and 4-hydroxycumarin in biodegradable choline chloride based deep eutectic solvent in good yields (50-95%). This green procedure has the advantages of higher yields, shorter reaction times, environmental friendliness, and easy work-up.(c) 2014 Elsevier B.V. All rights reserved.

引用

收藏

页码：62 / 67

页数：6

相关论文

共 26 条

[1] Glycerol eutectics as sustainable solvent systems [J].

Abbott, Andrew P. ;

Harris, Robert C. ;

Ryder, Karl S. ;

D'Agostino, Carmine ;

Gladden, Lynn F. ;

Mantle, Mick D. .

GREEN CHEMISTRY, 2011, 13 (01) :82-90

[2] Novel solvent properties of choline chloride/urea mixtures [J].

Abbott, AP ;

Capper, G ;

Davies, DL ;

Rasheed, RK ;

Tambyrajah, V .

CHEMICAL COMMUNICATIONS, 2003, (01) :70-71

[3]

Andrew D.B., 2004, J AM CHEM SOC, V126, P9142

[4] Highly efficient deep eutectic solvent catalyzed ring opening of epoxides [J].

Azizi, Najmadin ;

Batebi, Elham .

CATALYSIS SCIENCE & TECHNOLOGY, 2012, 2 (12) :2445-2448

[5] Deep eutectic solvent promoted highly efficient synthesis of N, N′-diarylamidines and formamides [J].

Azizi, Najmadin ;

Gholibeglo, Elham ;

Babapour, Mahbobe ;

Ghafuri, Hossein ;

Bolourtchian, Seyed Mohammad .

COMPTES RENDUS CHIMIE, 2012, 15 (09) :768-773

[6] Natural deep eutectic salt promoted regioselective reduction of epoxides and carbonyl compounds [J].

Azizi, Najmadin ;

Batebi, Elham ;

Bagherpour, Said ;

Ghafuri, Hossein .

RSC ADVANCES, 2012, 2 (06) :2289-2293

[7] Systematics and nomenclature of bicyclic carbohydrogens. [J].

Baeyer, A .

BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1900, 33 :3771-3775

[8] Design, synthesis, and SAR of new pyrrole-oxindole progesterone receptor modulators leading to 5-(7-Fluoro-3,3-dimethyl-2-oxo-2,3-dihydro-1H-indol-5-yl)-1-methyl-1H-pyrrole-2-carbonitrile (WAY-255348) [J].

Fensome, Andrew ;

Adams, William R. ;

Adams, Andrea L. ;

Berrodin, Tom J. ;

Cohen, Jeff ;

Huselton, Christine ;

Illenberger, Arthur ;

Kern, Jeffrey C. ;

Hudak, Valerie A. ;

Marella, Michael A. ;

Melenski, Edward G. ;

McComas, Casey C. ;

Mugford, Cheryl A. ;

Slayden, Ov D. ;

Yudt, Matthew ;

Zhang, Zhiming ;

Zhang, Puwen ;

Zhu, Yuan ;

Winneker, Richard C. ;

Wrobel, Jay E. .

JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (06) :1861-1873

[9] Fluoride ion catalyzed multicomponent reactions for efficient synthesis of 4H-chromene and N-arylquinoline derivatives in aqueous media [J].

Gao, Shijay ;

Tsai, Cheng Hsuan ;

Tseng, Chi ;

Yao, Ching-Fa .

TETRAHEDRON, 2008, 64 (38) :9143-9149

[10] Gold(III) chloride (HAuCl4•3H2O) in PEG: A new and efficient catalytic system for the synthesis of functionalized spirochromenes [J].

Kidwai, Mazaahir ;

Jahan, Anwar ;

Mishra, Neeraj Kumar .

APPLIED CATALYSIS A-GENERAL, 2012, 425 :35-43