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Journal of Sol-Gel Science and Technology

, Volume 82, Issue 2, pp 432–439 | Cite as

Green synthesis of Ni–Cu–Mg ferrite nanoparticles using tragacanth gum and their use as an efficient catalyst for the synthesis of polyhydroquinoline derivatives

  • Saeid Taghavi Fardood
  • Ali Ramazani
  • Sajjad Moradi
Original Paper: Nano-structured materials (particles, fibers, colloids, composites, etc.)

Abstract

The use of natural gel is generating interest of researchers toward cost effective, nontoxic, economic viability and eco-friendly green synthesis of nanoparticles. In the present work, Ni0.35Cu0.25Mg0.4Fe2O4 MNPs were synthesized using tragacanth gum as biotemplate and Metals nitrate as the metal source by the sol–gel method without using any organic chemicals. The sample was characterized by powder X-ray diffraction, fourier transform infrared spectroscopy, vibrating sample magnetometer and scanning electron microscopy. The X-ray powder diffraction analysis revealed the formation of Cubic phase ferrite MNPs with average particle size of 19 nm. Thereupon, Ni–Cu–Mg ferrite nanoparticles as an efficient catalyst was used for the synthesis of polyhydroquinoline derivatives via multi-component reactions under microwave irradiation. Simple work-up, mild reaction conditions, short reaction times, use of an economically convenient catalyst, and excellent product yields (82–98%) are the advantageous features of this method. The catalyst could easily be recycled and reused six times without noticeable decrease in catalytic activity.

Graphical Abstract

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Keywords

Ferrites Tragacanth gum Sol–gel method Polyhydroquinoline Microwave irradiation 

Notes

Compliance with Ethical Standards

Conflict of Interest

The authors declare no conflict of interests.

References

  1. 1.
    Reddy MP, Madhuri W, Sadhana K, Kim I, Hui K, Hui K, Kumar KS, Reddy RR (2014) Microwave sintering of nickel ferrite nanoparticles processed via sol–gel method. J Sol Gel Sci Technol 70:400–404CrossRefGoogle Scholar
  2. 2.
    Kumar R, Kumar H, Singh RR, Barman P (2016) Variation in magnetic and structural properties of Co-doped Ni–Zn ferrite nanoparticles: a different aspect. J Sol Gel Sci Technol 78:566–575CrossRefGoogle Scholar
  3. 3.
    Taghavi Fardood S, Ramazani A (2016) Green Synthesis and Characterization of Copper Oxide Nanoparticles Using Coffee Powder Extract. J Nanostruct 6:167–171Google Scholar
  4. 4.
    Sadri F, Ramazani A, Massoudi A, Khoobi M, Tarasi R, Shafiee A, Azizkhani V, Dolatyari L, Joo SW (2014) Green oxidation of alcohols by using hydrogen peroxide in water in the presence of magnetic Fe3O4 nanoparticles as recoverable catalyst. Green Chem Lett Rev 7:257–264CrossRefGoogle Scholar
  5. 5.
    Cai X, Wang H, Zhang Q, Tong J (2014) Selective oxidation of styrene efficiently catalyzed by spinel Mg–Cu ferrite complex oxides in water. J Sol Gel Sci Technol 69:33–39CrossRefGoogle Scholar
  6. 6.
    Tong J, Cai X, Wang H, Xia C (2013) Efficient magnetic CoFe2O4 nanocrystal catalyst for aerobic oxidation of cyclohexane prepared by sol–gel auto-combustion method: effects of catalyst preparation parameters. J Sol Gel Sci Technol 66:452–459CrossRefGoogle Scholar
  7. 7.
    Nagarapu L, Kumari MD, Kumari NV, Kantevari S (2007) MCM-41 catalyzed rapid and efficient one-pot synthesis of polyhydroquinolines via the Hantzsch reaction under solvent-free conditions. Catal Commun 8:1871–1875CrossRefGoogle Scholar
  8. 8.
    Tayebee R, Maleki B, Ghadamgahi M (2012) Ammonium dihydrogen phosphate catalyst for one-pot synthesis of 3, 4-dihydropyrimidin-2 (1H)-ones. Chin J Catal 33:659–665CrossRefGoogle Scholar
  9. 9.
    Bahrami M, Ramazani A, Hanifehpour Y, Fattahi N, Fardood ST, Asiabi PA, Joo SW (2016) In-situ generated stabilized phosphorus ylides mediated a mild and efficient method for the preparation of some new sterically congested electron-poor N-vinylated heterocycles. Phosphorus Sulfur Silicon Relat Elem 191:1368–1374CrossRefGoogle Scholar
  10. 10.
    Ramazani A, Ahmadi Y, Fattahi N, Ahankar H, Pakzad M, Aghahosseini H, Rezaei A, Fardood ST, Joo SW (2016) Synthesis Of 1, 3, 4-oxadiazoles from the reaction Of N-isocyaniminotriphenylphosphorane (Nicitpp) with cyclohexanone, a primary amine and an aromatic carboxylic acid via intramolecular aza-wittig reaction of in-situ generated iminophosphoranes. Phosphorus Sulfur Silicon Relat Elem 191:1057–1062CrossRefGoogle Scholar
  11. 11.
    Mager P, Coburn R, Solo A, Triggle D, Rothe H (1992) QSAR, diagnostic statistics and molecular modelling of 1, 4-dihydropyridine calcium antagonists: a difficult road ahead. Drug Des Discovery 8:273–289Google Scholar
  12. 12.
    Kawase M, Shah A, Gaveriya H, Motohashi N, Sakagami H, Varga A, Molnár J (2002) 3, 5-Dibenzoyl-1, 4-dihydropyridines: synthesis and MDR reversal in tumor cells. Biorg Med Chem 10:1051–1055CrossRefGoogle Scholar
  13. 13.
    Rouffet M, de Oliveira CAF, Udi Y, Agrawal A, Sagi I, McCammon JA, Cohen SM (2010) From sensors to silencers: quinoline-and benzimidazole-sulfonamides as inhibitors for zinc proteases. J Am Chem Soc 132:8232–8233CrossRefGoogle Scholar
  14. 14.
    Buhler FR, Kiowski W (1987) Calcium antagonists in hypertension. J Hypertens 5:3–10CrossRefGoogle Scholar
  15. 15.
    Reid J, Meredith P, Pasanisi F (1985) Clinical pharmacological aspects of calcium antagonists and their therapeutic role in hypertension. J Cardiovasc Pharmacol 7:18–20CrossRefGoogle Scholar
  16. 16.
    Mekheimer RA, Hameed AA, Sadek KU (2008) Solar thermochemical reactions: four-component synthesis of polyhydroquinoline derivatives induced by solar thermal energy. Green Chem 10:592–593CrossRefGoogle Scholar
  17. 17.
    Sapkal SB, Shelke KF, Shingate BB, Shingare MS (2009) Nickel nanoparticle-catalyzed facile and efficient one-pot synthesis of polyhydroquinoline derivatives via Hantzsch condensation under solvent-free conditions. Tetrahedron Lett 50:1754–1756CrossRefGoogle Scholar
  18. 18.
    Kumar S, Sharma P, Kapoor KK, Hundal MS (2008) An efficient, catalyst-and solvent-free, four-component, and one-pot synthesis of polyhydroquinolines on grinding. Tetrahedron 64:536–542CrossRefGoogle Scholar
  19. 19.
    Wang L-M, Sheng J, Zhang L, Han J-W, Fan Z-Y, Tian H, Qian C-T (2005) Facile Yb (OTf)3 promoted one-pot synthesis of polyhydroquinoline derivatives through Hantzsch reaction. Tetrahedron 61:1539–1543CrossRefGoogle Scholar
  20. 20.
    Zhang X-Y, Li Y-Z, Fan X-S, Qu G-R, Hu X-Y, Wang J-J (2006) Multicomponent Reaction in Ionic Liquid: A Novel and Green Synthesis of 1, 4-Dihydropyridme Derivatives. Chin Chem Lett 17:150–152Google Scholar
  21. 21.
    Reddy CS, Raghu M (2008) Cerium (IV) ammonium nitrate catalysed facile and efficient synthesis of polyhydroquinoline derivatives through Hantzsch multicomponent condensation. Chin Chem Lett 19:775–779CrossRefGoogle Scholar
  22. 22.
    Maheswara M, Siddaiah V, Damu GLV, Rao CV (2006) An efficient one-pot synthesis of polyhydroquinoline derivatives via Hantzsch condensation using a heterogeneous catalyst under solvent-free conditions. Arkivoc 2:201–206Google Scholar
  23. 23.
    Katkar S, Arbad B, Lande M (2011) ZnO-Beta zeolite catalyzed solvent-free synthesis of polyhydroquinoline derivatives under microwave irradiation. Arab J Sci Eng 36:39–46CrossRefGoogle Scholar
  24. 24.
    Safaei-Ghomi J, Ghasemzadeh M (2012) Nanocrystalline copper (II) oxide-catalyzed one-pot four-component synthesis of polyhydroquinoline derivativesunder solvent-free conditions. J Nanostruct 1:243–248Google Scholar
  25. 25.
    Kassaee M, Masrouri H, Movahedi F (2010) ZnO-nanoparticle-promoted synthesis of polyhydroquinoline derivatives via multicomponent Hantzsch reaction. Monatsh Chem 141:317–322CrossRefGoogle Scholar
  26. 26.
    Joshi VM, Pawar RP (2013) Microwave assisted expeditious synthesis of bioactive polyhydroquinoline derivatives. Eur Chem Bull 2:679–682Google Scholar
  27. 27.
    Mobinikhaledi A, Foroughifar N, Fard MAB, Moghanian H, Ebrahimi S, Kalhor M (2009) Efficient one-pot synthesis of polyhydroquinoline derivatives using silica sulfuric acid as a heterogeneous and reusable catalyst under conventional heating and energy-saving microwave irradiation. Synth Commun 39:1166–1174CrossRefGoogle Scholar
  28. 28.
    Draget K (2009) Alginates. In: Phillips G, & Williams P (eds) Handbook of hydrocolloids. Woodhead Publishing, Cambridge, pp 807–828CrossRefGoogle Scholar
  29. 29.
    Zohuriaan M, Shokrolahi F (2004) Thermal studies on natural and modified gums. Polym Test 23:575–579CrossRefGoogle Scholar
  30. 30.
    Ishaque M, Islam M, Khan MA, Rahman I, Genson A, Hampshire S (2010) Structural, electrical and dielectric properties of yttrium substituted nickel ferrites. Physica B 405:1532–1540CrossRefGoogle Scholar
  31. 31.
    Waldron R (1955) Infrared spectra of ferrites. Phys Rev 99:1727CrossRefGoogle Scholar
  32. 32.
    Batoo KM, Kumar S, Lee CG (2009) Influence of Al doping on electrical properties of Ni–Cd nano ferrites. Curr Appl Phys 9:826–832CrossRefGoogle Scholar
  33. 33.
    Sainani J, Shah A, Arya V (1994) Synthesis of 4-aryl-1, 4, 5, 6, 7, 8-Hexahydro-5-oxo-2, 7, 7-trimethyl-quinoline-3-carboxylates and amides. Indian J Chem Sect B 33:526–531Google Scholar
  34. 34.
    Li BL, Zhong AG, Ying AG (2015) Novel SO3H‐functionalized ionic liquids–catalyzed facile and efficient synthesis of polyhydroquinoline derivatives via hantzsch condensation under ultrasound irradiation. J Heterocycl Chem 52:445–449CrossRefGoogle Scholar
  35. 35.
    Maleki B, Tayebee R, Kermanian M, Sedigh Ashrafi S (2013) One-Pot Synthesis of 1, 8-Dioxodecahydroacridines and Polyhydroquinoline using 1, 3-Di (bromo or chloro)-5, 5-Dimethylhydantoin as a Novel and Green Catalyst under Solvent-Free Conditions. J Mex Chem Soc 57:290–297Google Scholar
  36. 36.
    Puri S, Kaur B, Parmar A, Kumar H (2011) Copper perchlorate hexahydrate: an efficient catalyst for the green synthesis of polyhydroquinolines under ultrasonication. ISRN Org Chem 2011:1–4CrossRefGoogle Scholar
  37. 37.
    Mohammadi Ziarani G, Badiei AR, Khaniania Y, Haddadpour M (2010) One pot synthesis of polyhydroquinolines catalyzed by sulfonic acid functionalized SBA-15 as a new nanoporous acid catalyst under solvent free conditions. Iran J Chem Chem Eng 29:1–10Google Scholar
  38. 38.
    Sanaeishoar T, Roueen S (2011) P2O5/AL2O3 As an an effieient catalyst for one-pot synthesis of polyhydroquinoline derivatives under solvent-free conditions. Int J Heterocyclic Chem 1:17–22Google Scholar
  39. 39.
    Karade NN, Budhewar VH, Shinde SV, Jadhav WN (2007) L-proline as an efficient organo-catalyst for the synthesis of polyhydroquinoline via multicomponent Hantzsch reaction. Lett Org Chem 4:16–19CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2017

Authors and Affiliations

  1. 1.Department of ChemistryUniversity of ZanjanZanjanIran

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