Trihydrazinotriazine-grafting Fe3O4/SiO2 core-shell nanoparticles with expanded porous structure for organic reactions

Jamal Rahimi, Seyedeh Shadi Mirmohammadi, Ali Maleki

PDF(4484 KB)
PDF(4484 KB)
Front. Chem. Sci. Eng. ›› 2021, Vol. 15 ›› Issue (4) : 1008-1020. DOI: 10.1007/s11705-020-1996-8
RESEARCH ARTICLE
RESEARCH ARTICLE

Trihydrazinotriazine-grafting Fe3O4/SiO2 core-shell nanoparticles with expanded porous structure for organic reactions

Author information +
History +

Abstract

This study focuses on the synthesis and characterization of a novel magnetic nanocomposite 2,4,6-trihydrazino-1,3,5-triazine (THDT)-functionalized with silica-coated iron oxide magnetic nanoparticles (MNPs). This nanocomposite has porous morphology decorated with the spherical MNPs. Through co-precipitation of iron salts, MNPs were obtained. The prepared THDT was placed on the chlorine surface-modified MNPs. The present environment-friendly nanocatalyst intensely accelerated the synthesis of highly functionalized tetrahydrobenzo[b]pyran derivatives as well as reduced the reaction times and increased yields of the products.

Graphical abstract

Keywords

trihydrazino-triazine / porous / magnetic nanocatalyst / green chemistry / tetrahydrobenzo[b]pyrans

Cite this article

Download citation ▾
Jamal Rahimi, Seyedeh Shadi Mirmohammadi, Ali Maleki. Trihydrazinotriazine-grafting Fe3O4/SiO2 core-shell nanoparticles with expanded porous structure for organic reactions. Front. Chem. Sci. Eng., 2021, 15(4): 1008‒1020 https://doi.org/10.1007/s11705-020-1996-8

References

[1]
Wu L, Mendoza-Garcia A, Li Q, Sun S. Organic phase syntheses of magnetic nanoparticles and their applications. Chemical Reviews, 2016, 116: 10473–10512
[2]
Polshettiwar V, Luque R, Fihri A, Zhu H, Bouhrara M, Basset J M. Magnetically recoverable nanocatalysts. Chemical Reviews, 2011, 111: 3036–3075
[3]
Maleki A, Rahimi J, Demchuk O M, Wilczewska A Z, Jasiński R. Green in water sonochemical synthesis of tetrazolopyrimidine derivatives by a novel core-shell magnetic nanostructure catalyst. Ultrasonics Sonochemistry, 2018, 43: 262–271
[4]
Wang D, Astruc D. Fast-growing field of magnetically recyclable nanocatalysts. Chemical Reviews, 2014, 114: 6949–6985
[5]
Hu Y, Zheng S, Zhang F. Fabrication of MIL-100(Fe)@SiO2@Fe3O4 core-shell microspheres as a magnetically recyclable solid acidic catalyst for the acetalization of benzaldehyde and glycol. Frontiers of Chemical Science and Engineering, 2016, 10(4): 534–541
[6]
Yuan E, Ren X, Wang L, Zhao W. A comparison of the catalytic hydrogenation of 2-amylanthraquinone and 2-ethylanthraquinone over a Pd/Al2O3 catalyst. Frontiers of Chemical Science and Engineering, 2017, 11(2): 177–184
CrossRef Google scholar
[7]
Wu D, Xu F, Sun B, Fu R, He H, Matyjaszewski K. Design and preparation of porous polymers. Chemical Reviews, 2012, 112(7): 3959–4015
CrossRef Google scholar
[8]
Bo L, Sun S. Microwave-assisted catalytic oxidation of gaseous toluene with a Cu-Mn-Ce/cordierite honeycomb catalyst. Frontiers of Chemical Science and Engineering, 2019, 13(2): 385–392
CrossRef Google scholar
[9]
Mohapatra M, Anand S. Synthesis and applications of nano-structured iron oxides/hydroxides—a review. International Journal of Engineering Science and Technology, 2010, 2(8): 127–146
[10]
Maleki A, Azadegan S, Rahimi J. Gallic acid grafted to amine-functionalized magnetic nanoparticles as a proficient catalyst for environmentally friendly synthesis of a-aminonitriles. Applied Organometallic Chemistry, 2019, 33(5): e4810
CrossRef Google scholar
[11]
Mohammadi A A, Asghariganjeh M R, Hadadzahmatkesh A. Synthesis of tetrahydrobenzo[b]pyran under catalysis of NH4Al(SO4)2·12H2O (Alum). Arabian Journal of Chemistry, 2017, 10: 2213–2216
CrossRef Google scholar
[12]
Maleki A, Rahimi J, Hajizadeh Z, Niksefat M. Synthesis and characterization of an acidic nanostructure based on magnetic polyvinyl alcohol as an efficient heterogeneous nanocatalyst for the synthesis of a-aminonitriles. Journal of Organometallic Chemistry, 2019, 881: 58–65
CrossRef Google scholar
[13]
Maleki A, Niksefat M, Rahimi J, Hajizadeh Z. Design and preparation of Fe3O4@PVA polymeric magnetic nanocomposite film and surface coating by sulfonic acid via in situ methods and evaluation of its catalytic performance in the synthesis of dihydropyrimidines. BMC Chemistry, 2019, 13(1): 19
CrossRef Google scholar
[14]
Maleki A, Rahimi J. Synthesis of dihydroquinazolinone and octahydroquinazolinone and benzimidazoloquinazolinone derivatives catalyzed by an efficient magnetically recoverable GO-based nanocomposite. Journal of Porous Materials, 2018, 25(6): 1–8
CrossRef Google scholar
[15]
Elhamifar D, Ramazani Z, Norouzi M, Mirbagheri R. Magnetic iron oxide/phenylsulfonic acid: a novel, efficient and recoverable nanocatalyst for green synthesis of tetrahydrobenzo[b]pyrans under ultrasonic conditions. Journal of Colloid and Interface Science, 2018, 511: 392–401
CrossRef Google scholar
[16]
Maleki A, Hamidi N, Maleki S, Rahimi J. Surface modified SPIONs-Cr (VI) ions-immobilized organic-inorganic hybrid as a magnetically recyclable nanocatalyst for rapid synthesis of polyhydroquinolines under solvent-free conditions at room temperature. Applied Organometallic Chemistry, 2017, 32(4): e4245
CrossRef Google scholar
[17]
Dinari M, Hatami M. Novel N-riched crystalline covalent organic framework as a highly porous adsorbent for effective cadmium removal. Journal of Environmental Chemical Engineering, 2019, 7(1): 102907
CrossRef Google scholar
[18]
Taheri-Ledari R, Rahimi J, Maleki A. Method screening for conjugation of the small molecules onto the vinyl-coated Fe3O4/silica nanoparticles: highlighting the efficiency of ultrasonication. Materials Research Express, 2020, 7(1): 015067
CrossRef Google scholar
[19]
Yaoting F, Gang L, Zifeng L, Hongwei H, Hairong M. Synthesis, structure and third-order nonlinear optical properties of 1,3,5-triazine-based Zn(II) three-dimensional supramolecule. Journal of Molecular Structure, 2004, 693(1-3): 217–224
CrossRef Google scholar
[20]
Zhuang L, Zhang W, Zhao Y, Shen H, Lin H, Liang J. Preparation and characterization of Fe3O4 particles with novel nanosheets morphology and magnetochromatic property by a modified solvothermal method. Scientific Reports, 2015, 5(1): 9320
CrossRef Google scholar
[21]
Huang H, Shende C, Sengupta A, Inscore F, Brouillette C, Smith W, Farquharson S. Surface-enhanced Raman spectra of melamine and other chemicals using a 1550 nm (retina-safe) laser. Journal of Raman Spectroscopy : JRS, 2012, 43(6): 701–705
CrossRef Google scholar
[22]
Maleki A, Ghalavand R, Firouzi Haji R. Synthesis and characterization of the novel diamine-functionalized Fe3O4@SiO2 nanocatalyst and its application for one-pot three-component synthesis of chromenes. Applied Organometallic Chemistry, 2018, 32(1): e3916
CrossRef Google scholar
[23]
Khazaei A, Gholami F, Khakyzadeh V, Moosavi-Zare A R, Afsar J. Magnetic core-shell titanium dioxide nanoparticles as an efficient catalyst for domino Knoevenagel-Michael-cyclocondensation reaction of malononitrile, various aldehydes and dimedone. RSC Advances, 2015, 5(19): 14305–14310
CrossRef Google scholar
[24]
Maleki A, Azadegan S. Preparation and characterization of silica-supported magnetic nanocatalyst and application in the synthesis of 2-amino-4-H-chromene-3-carbonitrile derivatives. Inorganic and Nano-Metal Chemistry, 2017, 47(6): 917–924
CrossRef Google scholar
[25]
Zonouz A M, Okhravi S, Moghani D. Ammonium acetate as a catalyst and/or reactant in the reaction of dimedone, aromatic aldehyde, and malononitrile: synthesis of tetrahydrobenzo[b]pyrans and hexahydroquinolines. Monatshefte für Chemie-Chemical Monthly, 2016, 147(10): 1819–1824
CrossRef Google scholar
[26]
Bodaghifard M A, Mobinikhaledi A, Asadbegi S. Bis(4-pyridylamino) triazine-stabilized magnetite nanoparticles: preparation, characterization and application as a retrievable catalyst for the green synthesis of 4H-pyran, 4H-thiopyran and 1,4-dihydropyridine derivatives. Applied Organometallic Chemistry, 2017, 31(2): e3557
CrossRef Google scholar
[27]
Niknam K, Borazjani N, Rashidian R, Jamali A. Silica-bonded N-propylpiperazine sodium n-propionate as recyclable catalyst for synthesis of 4H-pyran derivatives. Chinese Journal of Catalysis, 2013, 34(12): 2245–2254
CrossRef Google scholar

Acknowledgments

This work was partially supported by the research council of the Iran University of Science and Technology. We also would like to thank Maryam Niksefat, Ehsan Morshedloo and Peyman Hanifenejad for their help in graphic drawing.

RIGHTS & PERMISSIONS

2020 Higher Education Press
AI Summary AI Mindmap
PDF(4484 KB)

Accesses

Citations

Detail

Sections
Recommended

/