Efficient one-pot four-component synthesis of 1,4-dihydropyridines promoted by magnetite/chitosan as a magnetically recyclable heterogeneous nanocatalyst

Maleki, Ali; Kamalzare, Maryam; Aghaei, Morteza

doi:10.1007/s40097-014-0140-z

Cited by 60 publications

(21 citation statements)

References 55 publications

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“…The isolated yields were 97, 95, 94, 92, 91 and 90% for the fresh catalyst and five subsequent recycled runs, respectively. As a result, the catalytic performance and recyclability of Fe 3 O 4 /SiO 2 -OSO 3 H were better than catalysts previously reported in the literature [8][9][10][11][12] and also our earlier works [13,20].…”

Section: Resultscontrasting

confidence: 44%

“…Our group previous works have been on preparation and application of nanostructure heterogeneous catalysts in chemical reactions, especially MCRs [16][17][18][19][20][21][22][23]; in this article, we want to describe the practical synthesis and theoretical prediction of the pharmacological and biological activities of polyhydroquinoline derivatives 4-37. In this purpose, sulfonated silica-based magnetic nanocatalyst (Fe 3 O 4 /SiO 2 -OSO 3 H) was used as a green heterogeneous nanocatalyst in a one-pot MCR starting from diverse aromatic and heteroaromatic aldehyde 1, dimedone/cyclohexandione 2, ethyl-or methyl-acetoacetate 3 and NH 4 OAc.…”

Section: Introductionmentioning

confidence: 99%

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Green synthesis of polyhydroquinolines via MCR using Fe3O4/SiO2-OSO3H nanostructure catalyst and prediction of their pharmacological and biological activities by PASS

2017

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In this work, a library of diverse chemically and medicinally important heterocyclic polyhydroquinoline derivatives was efficiently prepared via a one-pot multicomponent reaction starting from various raw materials including aromatic aldehydes, dimedone or 1,3-cyclohexandione, ethyl acetoacetate or methyl acetoacetate and ammonium acetate in the presence of Fe 3 O 4 /SiO 2 -OSO 3 H as a sulfonated silica-based magnetic nanocatalyst in high yields. Main advantages of the present practical approach are ready availability of starting materials, non-toxicity, inexpensiveness, ease of workup procedure, diversity orientation synthesis and an eco-friendly nature of the reaction. The nanocatalyst was characterized by Fourier transform infrared (FT-IR) spectra, scanning electron microscopy (SEM) images and energy-dispersive X-ray spectroscopy (EDX) spectra. The nanocatalyst was simply recovered using an external magnet and reused several times. Then, the pharmacological and biological activities of the products were theoretically examined by the prediction of activity spectra for substances (PASS) program.

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Section: Resultscontrasting

confidence: 44%

Section: Introductionmentioning

confidence: 99%

Green synthesis of polyhydroquinolines via MCR using Fe3O4/SiO2-OSO3H nanostructure catalyst and prediction of their pharmacological and biological activities by PASS

2017

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“…The area of nanocatalysis which involves a substance or material with catalytic properties that possesses at least one nanoscale dimension in their structures is undergoing an explosive development. Nanocatalysis can help design catalysts with excellent activity, greater selectivity, and high stability [5][6][7][8]. Composite nanocatalysts, especially supported magnetic metal oxides nanoparticles (MNPs), have attracted considerable interest of researchers, because of their potential applications in chemical, biomedical and materials science.…”

Section: Introductionmentioning

confidence: 99%

Design and development of a novel magnetic camphor nanospheres core/shell nanostructure

2017

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In this work, the first synthesis, characterization and catalytic performance of Fe 3 O 4 /camphor core/shell nanospheres as a magnetic composite nanocatalyst were reported. The characterization was carried out by Fourier transform infrared spectroscopy, field-emission scanning electron microscopy, transmission electron microscopy, X-ray diffraction, energy-dispersive X-ray spectroscopy, thermogravimetric analysis, vibrating sample magnetometer, N 2 adsorption-desorption by Brunauer-Emmett-Teller and inductively coupled plasma analyses. The recoverable heterogeneous nanostructure catalyst was simply prepared and effectively employed in the one-pot multicomponent synthesis of b-amino carbonyl compounds in ethanol as a green solvent at room temperature. Further advantages of this new protocol are short reaction times, high yields, easy workup procedure, inexpensive and eco-friendly protocol and magnetically recoverability and several times reusability of the nanocatalyst without significant decrease in catalytic activity.

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“…Specifically, chitosan has been also applied as a catalyst. In this regard, several catalytic systems using chitosan and magnetic nanoparticles coated with chitosan have been developed [21][22][23][24][25][26]. In addition, functionalization of amine and hydroxyl groups in chitosan provides coordination sites for a variety of chemical modifications and as a result, presents catalysts for different kinds of organic reaction such as oxidation, coupling and multi-component reactions, etc [27][28][29][30].…”

Section: Introductionmentioning

confidence: 99%

Fe₃O₄@chitosan‐bound picolinaldehyde Cu complex as the magnetically reusable nanocatalyst for adjustable oxidation of sulfides

Fakhri

Naghipour

2017

Env Prog and Sustain Energy

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As ecological and environmental demands for sustainability are one of the most strategic landscapes in the green chemistry, recent chemical researches have been directed toward eco‐friendly catalysts. Further advancement in this area has presented magnetically recoverable nanocatalyst. Herein, Cu‐based nanocatalyst was synthesized via reaction of picolinaldehyde and amine group of immobilized chitosan on the magnetic nanosupport, and followed by metallation. The prepared nanocatalyst was characterized by a variety of techniques. FT‐IR analysis demonstrated the favored coating of chitosan‐based Cu complex over Fe3O4 nanoparticles. The scanning electron microscopy and transmission electron microscope techniques confirmed nano‐sized of the catalyst. Fe3O4 nanoparticles and the nanocatalyst fit the X‐ray diffraction pattern of standard magnetite. High thermal stability of the nanocatalyst was determined by the TGA analysis. The inductively coupled plasma atomic emission analysis technique specified content of Cu was 0.62 mmol/g. Magnetic properties were analyzed by the vibrating sample magnetometer study. Regarding green chemistry goals, the applicability of this nanocatalyst was tested in the oxidation of sulfides derivatives. The nanocatalyst exhibited high catalytic activity and selectivity in the oxidation of sulfides to the corresponding sulfoxide (without over‐oxidation of sulfides to sulfones) under green conditions. Based on the magnetic properties (alluded to the Fe3O4 component), the nanocatalyst could be easily recovered from the reaction mixture using an external magnet, and reused up to four times without noticeable deterioration in its performance. Moreover, the other merits such as high yields, mild reaction condition, use of stable and green oxidant and eco‐friendly procedure made this nanocatalyst as a valuable catalyst in practical synthesis. © 2017 American Institute of Chemical Engineers Environ Prog, 37: 1626–1631, 2018

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Efficient one-pot four-component synthesis of 1,4-dihydropyridines promoted by magnetite/chitosan as a magnetically recyclable heterogeneous nanocatalyst

Cited by 60 publications

References 55 publications

Green synthesis of polyhydroquinolines via MCR using Fe3O4/SiO2-OSO3H nanostructure catalyst and prediction of their pharmacological and biological activities by PASS

Green synthesis of polyhydroquinolines via MCR using Fe3O4/SiO2-OSO3H nanostructure catalyst and prediction of their pharmacological and biological activities by PASS

Design and development of a novel magnetic camphor nanospheres core/shell nanostructure

Fe₃O₄@chitosan‐bound picolinaldehyde Cu complex as the magnetically reusable nanocatalyst for adjustable oxidation of sulfides

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Efficient one-pot four-component synthesis of 1,4-dihydropyridines promoted by magnetite/chitosan as a magnetically recyclable heterogeneous nanocatalyst

Cited by 60 publications

References 55 publications

Green synthesis of polyhydroquinolines via MCR using Fe3O4/SiO2-OSO3H nanostructure catalyst and prediction of their pharmacological and biological activities by PASS

Green synthesis of polyhydroquinolines via MCR using Fe3O4/SiO2-OSO3H nanostructure catalyst and prediction of their pharmacological and biological activities by PASS

Design and development of a novel magnetic camphor nanospheres core/shell nanostructure

Fe3O4@chitosan‐bound picolinaldehyde Cu complex as the magnetically reusable nanocatalyst for adjustable oxidation of sulfides

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Product

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Fe₃O₄@chitosan‐bound picolinaldehyde Cu complex as the magnetically reusable nanocatalyst for adjustable oxidation of sulfides