Durable magnetite-chitosan core-shell nanoparticles as reusable green nanocatalyst for the benign one-pot three-component synthesis of spirooxindoles and spirochromenes at ambient temperature under both solvent-free and ultrasonic conditions in aqueous ethanol solution

被引:2
作者
Mardaneh, Pegah [1 ]
Sardarian, Ali Reza [1 ]
机构
[1] Shiraz Univ, Coll Sci, Dept Chem, Shiraz 7145685464, Iran
基金
美国国家科学基金会;
关键词
Superparamagnetic; Green nanocatalyst; Spirooxindoles; Spirochromenes; Solvent-free; Ultrasonic condition; RECYCLABLE CATALYST; FE3O4; NANOPARTICLES; HIGHLY EFFICIENT; L-PROLINE; ACID;
D O I
10.1007/s13738-023-02919-2
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In the present research, a novel, efficient, and green nanocatalyst has been afforded by coating Fe3O4 nanoparticles with chitosan through simple and readily available chemicals. Fourier-transform infrared spectroscopy, X-ray diffraction, scanning electron microscopy, dynamic light scattering, vibrating sample magnetometer, and thermogravimetric analyses were used to describe this nanocatalyst. The catalytic performance of the Fe3O4@chitosan heterogeneous nanocatalyst was investigated in an environmentally benign and efficacious fabrication of a variety of spirooxindole and spirochromene derivatives in high yields via employing three-component reactions of malononitrile, dimedone, and isatin in a solvent-free medium (Method A) and under ultrasonic conditions in EtOH/H2O (Method B) at ambient temperature. The achieved nanocatalyst could be easily removed from the mixture of the reaction and was recyclable seven times via a simple external magnet without appreciable loss in catalytic proficiency. Several other advantages of this methodology were environmental friendliness, simple operation, excellent yields, economical handling, and easy workup.
引用
收藏
页码:211 / 225
页数:15
相关论文
共 61 条
[1]   A green synthesis of spirooxindole derivatives catalyzed by SiO2@g-C3N4 nanocomposite [J].
Allahresani, Ali ;
Taheri, Bahare ;
Nasseri, Mohammad Ali .
RESEARCH ON CHEMICAL INTERMEDIATES, 2018, 44 (02) :1173-1188
[2]  
Azarnier SG., 2022, RES SQ, DOI [10.1038/s41598-022-10102-5, DOI 10.1038/S41598-022-10102-5]
[3]   Protic guanidinium ionic liquid as a green and highly efficient catalyst for the synthesis of functionalized spirochromenes under solvent-free conditions [J].
Baghbanian, Seyed Meysam ;
Tajbakhsh, Mahmood ;
Farhang, Maryam .
COMPTES RENDUS CHIMIE, 2014, 17 (12) :1160-1164
[4]   Isatin-based three-component synthesis of new spirooxindoles using magnetic nano-sized copper ferrite [J].
Baghernejad, Mojtaba ;
Khodabakhshi, Saeed ;
Tajik, Sanaz .
NEW JOURNAL OF CHEMISTRY, 2016, 40 (03) :2704-2709
[5]   Ultrasound promoted one-pot synthesis of 2-amino-4,8-dihydropyrano [3,2-b]pyran-3-carbonitrile scaffolds in aqueous media: A complementary 'green chemistry' tool to organic synthesis [J].
Banitaba, Sayed Hossein ;
Safari, Javad ;
Khalili, Shiva Dehghan .
ULTRASONICS SONOCHEMISTRY, 2013, 20 (01) :401-407
[6]   Synthesis of mono- and bis-spirooxindole derivatives "on water" using double salt of aluminum sulfate-sulfuric acid as a reusable catalyst [J].
Bashkar, Mohammad ;
Bavadi, Masoumeh ;
Ghaderi, Esmali ;
Niknam, Khodabakhsh .
MOLECULAR DIVERSITY, 2021, 25 (04) :2001-2015
[7]   Copper Ferrite Nanoparticles: An Efficient and Reusable Nanocatalyst for a Green One-Pot, Three-component Synthesis of Spirooxindoles in Water [J].
Bazgir, Ayoob ;
Hosseini, Ghaffar ;
Ghahremanzadeh, Ramin .
ACS COMBINATORIAL SCIENCE, 2013, 15 (10) :530-534
[8]   Engaging Isatins in Multicomponent Reactions (MCRs) - Easy Access to Structural Diversity [J].
Brandao, Pedro ;
Marques, Carolina S. ;
Carreiro, Elisabete P. ;
Pineiro, M. ;
Burke, Anthony J. .
CHEMICAL RECORD, 2021, 21 (04) :924-1037
[9]   Oxalic acid dihydrate: proline as a new recyclable designer solvent: a sustainable, green avenue for the synthesis of spirooxindole [J].
Chandam, Dattatray R. ;
Mulik, Abhijeet G. ;
Patil, Dayanand R. ;
Deshmukh, Madhukar B. .
RESEARCH ON CHEMICAL INTERMEDIATES, 2016, 42 (02) :1411-1423
[10]  
Chaudhary A., 2018, GREEN CHEM ENV SUSTA, P15, DOI [10.1007/978-981-10-8390-7_2, DOI 10.1007/978-981-10-8390-7_2]