Greener synthesis of spirooxindole in deep eutectic solvent

被引：96
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
    Abbott, Andrew P.
    Harris, Robert C.
    Ryder, Karl S.
    D'Agostino, Carmine
    Gladden, Lynn F.
    Mantle, Mick D.
    [J]. GREEN CHEMISTRY, 2011, 13 (01) : 82 - 90
  • [2] Novel solvent properties of choline chloride/urea mixtures
    Abbott, AP
    Capper, G
    Davies, DL
    Rasheed, RK
    Tambyrajah, V
    [J]. 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
    Azizi, Najmadin
    Batebi, Elham
    [J]. CATALYSIS SCIENCE & TECHNOLOGY, 2012, 2 (12) : 2445 - 2448
  • [5] Deep eutectic solvent promoted highly efficient synthesis of N, N′-diarylamidines and formamides
    Azizi, Najmadin
    Gholibeglo, Elham
    Babapour, Mahbobe
    Ghafuri, Hossein
    Bolourtchian, Seyed Mohammad
    [J]. COMPTES RENDUS CHIMIE, 2012, 15 (09) : 768 - 773
  • [6] Natural deep eutectic salt promoted regioselective reduction of epoxides and carbonyl compounds
    Azizi, Najmadin
    Batebi, Elham
    Bagherpour, Said
    Ghafuri, Hossein
    [J]. RSC ADVANCES, 2012, 2 (06): : 2289 - 2293
  • [7] Systematics and nomenclature of bicyclic carbohydrogens.
    Baeyer, A
    [J]. 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)
    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.
    [J]. 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
    Gao, Shijay
    Tsai, Cheng Hsuan
    Tseng, Chi
    Yao, Ching-Fa
    [J]. 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
    Kidwai, Mazaahir
    Jahan, Anwar
    Mishra, Neeraj Kumar
    [J]. APPLIED CATALYSIS A-GENERAL, 2012, 425 : 35 - 43
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