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]   Fe3O4@SiO2-(Imine-Thiazole)-Cu(OAc)2 nanocomposite catalyzed one-pot three-component synthesis of 2-Substituted benzothiazoles using S8 as sulfur source [J].
Patra, Indrajit ;
Kadhim, Mustafa M. ;
Kzar, Hamzah H. ;
Mustafa, Yasser Fakri ;
Jameel, Huda Ahmed .
JOURNAL OF SULFUR CHEMISTRY, 2023, 44 (02) :217-231
[42]   Magnetic Cu0@HAP@γ-Fe2O3 nanoparticles: An efficient catalyst for one-pot three-component reaction for the synthesis of imidazo[1,2-a]pyridines [J].
Sun, Wei ;
Jiang, Wei ;
Zhu, Gan ;
Li, Yiqun .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2018, 873 :91-100
[43]   One-Pot, Sequential Four-Component Synthesis of Benzo[a]chromeno[2,3-c]phenazine Derivatives Using SiO2-SO3H as an Efficient and Recoverable Catalyst Under Conventional Heating and Microwave Irradiation [J].
Yazdani-Elah-Abadi, Afshin ;
Mohebat, Razieh ;
Maghsoodlou, Malek-Taher ;
Heydari, Reza .
POLYCYCLIC AROMATIC COMPOUNDS, 2018, 38 (01) :92-101
[44]   Novel AlCl3@nano Fe3O4-SiO2: a benign multi-layer magnetite nanocatalyst for the three-component one-pot synthesis of spiro[benzochromeno [2,3-d]pyrimidin-indolines] [J].
Nikoofar, Kobra ;
Arian, Zahra ;
Jahanbani, Hoorieh .
INORGANIC AND NANO-METAL CHEMISTRY, 2022, 52 (03) :365-374
[45]   Aminosalicylic Acid Hydrazone Dioxomolybdenum(VI) Complex: Synthesis, Spectral Characterization and Application as a Green Homogeneous Lewis Acid Catalyst for the One-Pot Three-Component Synthesis of 2-Amino-3-Cyano-4H-Pyrans [J].
Kargar, Hadi ;
Fallah-Mehrjardi, Mehdi ;
Munawar, Khurram Shahzad .
POLYCYCLIC AROMATIC COMPOUNDS, 2022, 42 (09) :6780-6793
[46]   Three-component one-pot synthesis of 4,6-diarylpyrimidin- 2(1H)-ones under solvent-free conditions in the presence of sulfamic acid as a green and reusable catalyst [J].
Majid M. Heravi ;
Leila Ranjbar ;
Fatemeh Derikvand ;
Behnoush Alimadadi .
Molecular Diversity, 2008, 12 :191-196
[47]   Three-component one-pot synthesis of 4,6-diarylpyrimidin-2(1H)-ones under solvent-free conditions in the presence of sulfamic acid as a green and reusable catalyst [J].
Heravi, Majid M. ;
Ranjbar, Leila ;
Derikvand, Fatemeh ;
Alimadadi, Behnoush .
MOLECULAR DIVERSITY, 2008, 12 (3-4) :191-196
[48]   A convenient green protocol for one-pot three-component synthesis of 2-amino-4H-chromene derivatives catalyzed by ilmenite (FeTiO3) as an efficient and reusable catalyst in water [J].
Ebadzadeh, B. ;
Ramazani, A. ;
Azizkhani, V. ;
Aghahosseini, H. ;
Joo, S. W. .
BULGARIAN CHEMICAL COMMUNICATIONS, 2016, 48 (02) :187-193
[49]   One-Pot Three-Component Synthesis of 2,4,5-Triaryl Imidazoles using Fe3O4@BisImid-CuBr Nanocomposite as an Ecofriendly and Efficient Magnetically Reusable Catalyst [J].
Al-Dolaimy, F. ;
Alsalamy, Ali H. ;
Abdullah Abbas, Hussein ;
Rasen, Fadhil A. ;
Abdulhussein, Zaid ;
Ramadan, Montather F. ;
Abbas, Ahmed Hussien R. ;
Mustafa, Hesham S. .
CHEMISTRYSELECT, 2024, 9 (15)
[50]   A facile one-pot, three-component synthesis of 3,3′-(4-arylpyridine-2,6-diyl)bis(2H-chromen-2-one) derivatives under microwave irradiation [J].
Jian-Feng Zhou ;
Xiao-Jun Sun ;
Feng-Wen Lou ;
Meng Lv ;
Lu-Lu Zhang .
Research on Chemical Intermediates, 2013, 39 :1401-1408