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

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.

Key words： trihydrazino-triazine; porous; magnetic nanocatalyst; green chemistry; tetrahydrobenzo[b]pyrans

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.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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