A green one-pot three-component synthesis of spirooxindoles under conventional heating conditions or microwave irradiation by using Fe3O4@SiO2-imid-PMAn magnetic porous nanospheres as a recyclable catalyst

被引:41
|
作者
Esmaeilpour, Mohsen [1 ]
Javidi, Jaber [2 ,3 ]
Divar, Masoumeh [1 ]
机构
[1] Shiraz Univ, Coll Sci, Dept Chem, Shiraz, Iran
[2] Shahid Beheshti Univ Med Sci, Sch Pharm, Dept Pharmaceut, Tehran, Iran
[3] Shahid Beheshti Univ Med Sci, Sch Pharm, Students Res Comm, Tehran, Iran
基金
美国国家科学基金会;
关键词
Spirooxindoles; Multicomponent reactions; Green synthesis; One-pot reactions; Microwave irradiation; Magnetic separation; MULTICOMPONENT REACTIONS; EFFICIENT SYNTHESIS; REUSABLE CATALYST; NANOPARTICLES; DERIVATIVES; COPPER; NANOCATALYST; COMPLEX; NICKEL; HECK;
D O I
10.1016/j.jmmm.2016.09.020
中图分类号
T [工业技术];
学科分类号
08 ;
摘要
An efficient, green and environmentally procedure for the synthesis of spirooxindole derivatives has been developed by a one-pot three-component reaction of isatin derivatives, activated methylene, and 1,3-dicarbonyl compounds in the presence of Fe3O4@SiO2-imid-PMA(n) magnetic nanocatalyst under conventional heating conditions in water or microwave irradiation under solvent-free conditions. The reactions under conventional heating conditions were compared with the microwave-assisted reactions. The suggested method offers several advantages such as excellent yields, short reaction times, operational simplicity, a cleaner reaction, absence of any tedious workup or purification and ease of recovery and reusability of the catalyst by a magnetic field. In addition, the excellent catalytic performance in a water medium and the easy preparation, thermal stability and separation of the catalyst make it a good heterogeneous system and a useful alternative to other heterogeneous catalysts. The catalyst can be easily recovered by a magnetic field and reused for six consecutive reaction cycles without significant loss of activity. Also, the morphology of Fe3O4@SiO2-imid-PMA(n), particle size distribution and leaching of nano H3PMo12O40 (PMA(n)) after reaction cycles were investigated by scanning electron microscopy (SEM), dynamic light scattering (DLS), and inductively coupled plasma (ICP) analyzer.
引用
收藏
页码:232 / 240
页数:9
相关论文
共 50 条
  • [41] A facile one-pot, three-component synthesis of 3,3′-(4-arylpyridine-2,6-diyl)bis(2H-chromen-2-one) derivatives under microwave irradiation
    Zhou, Jian-Feng
    Sun, Xiao-Jun
    Lou, Feng-Wen
    Lv, Meng
    Zhang, Lu-Lu
    RESEARCH ON CHEMICAL INTERMEDIATES, 2013, 39 (03) : 1401 - 1408
  • [42] A facile one-pot, three-component synthesis of 3,3′-(4-arylpyridine-2,6-diyl)bis(2H-chromen-2-one) derivatives under microwave irradiation
    Jian-Feng Zhou
    Xiao-Jun Sun
    Feng-Wen Lou
    Meng Lv
    Lu-Lu Zhang
    Research on Chemical Intermediates, 2013, 39 : 1401 - 1408
  • [43] One-pot synthesis of 1-and 5-substituted 1H-tetrazoles using 1,4-dihydroxyanthraquinone-copper(II) supported on superparamagnetic Fe3O4@SiO2 magnetic porous nanospheres as a recyclable catalyst
    Esmaeilpour, Mohsen
    Javidi, Jaber
    Zahmatkesh, Saeed
    APPLIED ORGANOMETALLIC CHEMISTRY, 2016, 30 (11) : 897 - 904
  • [44] Sulfonated Porous Carbon (SPC): An efficient and recyclable solid acid catalyst for one-pot three-component synthesis of 2,3-dihydroquinazolin4(1H)-ones under solvent-free conditions
    Shokrolahi, Arash
    Zali, Abbas
    Zarei, Mohammad Ali
    Esmaeilpour, Karim
    IRANIAN JOURNAL OF CATALYSIS, 2012, 2 (02): : 91 - 94
  • [45] Three-Component One-Pot Synthesis of Quinazolin-4(3H)-one Derivatives Catalysed by Copper o-Toluenesulfonate under Mild Conditions
    Wang, Min
    Zhang, tingting
    Song, Zhiguo
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2010, 30 (05) : 740 - 744
  • [46] Al(H2PO4)3 as an Efficient and Reusable Catalyst for One-pot Three-component Synthesis of α-Amino Phosphonates under Solvent-free Conditions
    Maghsoodlou, Malek Taher
    Habibi-Khorassani, Sayyed Mostafa
    Heydari, Reza
    Hazeri, Nourollah
    Sajadikhah, Seyed Sajad
    Rostamizadeh, Mohsen
    CHINESE JOURNAL OF CHEMISTRY, 2010, 28 (02) : 285 - 288
  • [47] A green one-pot three-component syntheses of tetrazole under microwave irradiation using Ni Schiff base complex of mixed ligands on MCM-41 as an efficient heterogeneous catalyst
    Bharathi, M.
    Indira, S.
    Vinoth, G.
    Leslee, Denzil Britto Christopher
    Bharathi, K. Shanmuga
    JOURNAL OF POROUS MATERIALS, 2023, 30 (03) : 691 - 703
  • [48] Solvent-free, sonochemical, one-pot, four-component synthesis of 2H-indazolo[2,1-b]phthalazine-triones and 1H-pyrazolo[1,2-b]phthalazine-diones catalyzed by Fe3O4@SiO2-imid-PMAn magnetic nanoparticles
    Mohsen Esmaeilpour
    Jaber Javidi
    Fatemeh Nowroozi Dodeji
    Saeed Zahmatkesh
    Research on Chemical Intermediates, 2021, 47 : 2629 - 2652
  • [49] A green one-pot three-component syntheses of tetrazole under microwave irradiation using Ni Schiff base complex of mixed ligands on MCM-41 as an efficient heterogeneous catalyst
    M. Bharathi
    S. Indira
    G. Vinoth
    Denzil Britto Christopher Leslee
    K. Shanmuga Bharathi
    Journal of Porous Materials, 2023, 30 : 691 - 703
  • [50] Chitosan synergistically enhanced by successive Fe3O4 and silver nanoparticles as a novel green catalyst in one-pot, three-component synthesis of tetrahydrobenzo[α]xanthene-11-ones
    Mohammadi, Reza
    Eidi, Esmaiel
    Ghavami, Monireh
    Kassaee, Mohammad Zaman
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2014, 393 : 309 - 316