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
  • [21] A flexible one-pot synthesis of pyrazolopyridines catalyzed by Fe3O4@SiO2-SO3H nanocatalyst under microwave irradiation
    Safaei-Ghomi, J.
    Shahbazi-Alavi, H.
    SCIENTIA IRANICA, 2017, 24 (03) : 1209 - 1219
  • [22] A New One-Pot Three-Component Synthesis of 4-Aryl-6-cycloamino-1,3,5-triazin-2-amines under Microwave Irradiation
    Shahari, Muhammad Syafiq Bin
    Junaid, Ahmad
    Tiekink, Edward R. T.
    Dolzhenko, Anton, V
    SYNTHESIS-STUTTGART, 2021, 53 (14): : 2457 - 2468
  • [23] ONE-POT, THREE-COMPONENT SYNTHESIS OF α-AMINO PHOSPHONATES USING NaHSO4-SiO2 AS AN EFFICIENT AND REUSABLE CATALYST
    Maghsoodlou, Malek Taher
    Heydari, Reza
    Habibi-Khorassani, Sayyed Mostafa
    Hazeri, Nourallah
    Sajadikhah, Seyed Sajad
    Rostamizadeh, Mohsen
    Lashkari, Mojtaba
    SYNTHETIC COMMUNICATIONS, 2012, 42 (01) : 136 - 143
  • [24] Catalyst-free, one-pot, three-component synthesis of pyrimido[4,5-b]quinoline-4-amines under microwave irradiation
    Xu, Jiao
    Zhang, Li Hong
    Liu, Xiu Bo
    Ma, Wei
    Ma, Ling
    Ma, Yan
    Yang, Jian Nan
    Wang, Dao Lin
    JOURNAL OF CHEMICAL RESEARCH, 2018, (10) : 525 - 528
  • [25] Synthesis and characterization of Fe3O4@SiO2–polymer-imid–Pd magnetic porous nanospheres and their application as a novel recyclable catalyst for Sonogashira–Hagihara coupling reactions
    Esmaeilpour Mohsen
    Javidi Jaber
    Mokhtari Abarghoui Mehdi
    Nowroozi Dodeji Fatemeh
    Journal of the Iranian Chemical Society, 2014, 11 : 499 - 510
  • [26] A novel hydrophobic copper complex supported on γ-Fe2O3 as a magnetically heterogeneous catalyst for one-pot three-component synthesis of α-aminophosphonates
    Sobhani, Sara
    Khakzad, Fatemeh
    APPLIED ORGANOMETALLIC CHEMISTRY, 2017, 31 (12)
  • [27] Fe3O4 magnetic nanoparticles coated with a copolymer: a novel reusable catalyst for one-pot three-component synthesis of 2-amino-4H-chromene
    Keshavarz, Mahdieh
    Abdoli-Senejani, Masumeh
    Hojati, Seyedeh Fatemeh
    Askari, Shivadokht
    REACTION KINETICS MECHANISMS AND CATALYSIS, 2018, 124 (02) : 757 - 766
  • [28] One-pot three-component synthesis of pyrido [2′,1′: 2,3] imidazo[4,5-c] isoquinolines using Fe3O4@SiO2-OSO3H as an efficient heterogeneous nanocatalyst
    Maleki, Ali
    RSC ADVANCES, 2014, 4 (109): : 64169 - 64173
  • [29] Magnetic Co-doped NiFe2O4 Nanocomposite: A Heterogeneous and Recyclable Catalyst for the One-Pot Synthesis of Benzimidazoles, Benzoxazoles and Benzothiazoles under Solvent-Free Conditions
    Karimian, Azam
    Kakhki, Roya Mohammadzadeh
    Beidokhti, Hamideh Kargar
    JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2017, 64 (11) : 1316 - 1325
  • [30] Fe3O4-MNPs@MMT-K10: a reusable catalyst for synthesis of propargyl 4-aryl-4H-pyran-3-carboxyles via one-pot three-component reaction under microwave-assisted solvent-free conditions
    Thanh, Nguyen Dinh
    Hai, Do Son
    Huyen, Le Thi
    Thuy, Vu Thi Tuyet
    Tung, Do Tien
    Van, Hoang Thi Kim
    Toan, Vu Ngoc
    Giang, Nguyen Thi Kim
    Tri, Nguyen Minh
    RESEARCH ON CHEMICAL INTERMEDIATES, 2023, 49 (02) : 525 - 555