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Core-shell structured Fe3O4@MgO: magnetically recyclable nanocatalyst for one-pot synthesis of polyhydroquinoline derivatives under solvent-free conditions

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Abstract

Core-shell nanostructured Fe3O4@MgO catalyst was synthesized using a two-fold co-precipitation technique. High-resolution transmission electron microscopy (HR-TEM) images demonstrated that the catalyst had a core-shell framework with spherical morphology. In present study, Fe3O4@MgO is successfully used as an effective, novel, and recoverable nanocatalyst in an easy-to-follow, affordable, environment-friendly, and productive process for the synthesis of polyhydroquinoline derivatives via one-pot four-component Hantzsch condensation reaction. Importantly, magnetically retrievable Fe3O4@MgO nanoparticles provides high catalytic efficiency in solvent-free condition and can be used repeatedly up to six cycles without significant loss of catalytic activity. The study provides a greener route to yield 82-94% of polyhydroquinoline in a short reaction time under ultrasonication.

Graphical abstract

Fe3O4@MgO is a core-shell nanocatalyst that is reliable, affordable, heterogeneous, simple to handle, and recoverable. It can be used repeatedly for up to six cycles without significantly losing catalytic activity. The reaction was found to be effective in giving polyhydroquinoline yield of about 82-94 percent in short reaction times in solvent-free conditions.

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References

  1. Saleh S S, Salihi S S and Mohammed I A 2019 Biological activity Study for some heterocyclic compounds and their impact on the gram positive and negative bacteria Energy Proced. 157 296

    Article  CAS  Google Scholar 

  2. Heravi M M and Zadsirjan V 2020 Prescribed drugs containing nitrogen heterocycles: an overview RSC Adv. 10 44247

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  3. Kerru N, Gummidi L, Maddila S, Gangu K K and Jonnalagadda S B 2020 A review on recent advances in nitrogen-containing molecules and their biological applications Molecules 25 1909

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  4. Zarnegar Z 2015 Environmentally benign synthesis of polyhydroquinolines by Co3O4-CNT as an efficient heterogeneous catalyst Catal. Commun. 59 216

    Article  CAS  Google Scholar 

  5. Sirisha K, Achaiah G and Reddy V M 2010 Facile synthesis and antibacterial, antitubercular, and anticancer activities of novel 1,4-dihydropyridines Arch. Pharm. Chem. Life. Sci. 343 342

    Article  CAS  Google Scholar 

  6. Abdollahi-Alibeik M 2016 Fe3O4@B-MCM-41_a new magnetically recoverable nanostructured catalyst for the synthesis of polyhydroquinolines J. Magn. Mater. 398 205

    Article  CAS  Google Scholar 

  7. Nasr-Esfahani M 2014 Magnetic Fe3O4 nanoparticles: Efficient and recoverable nanocatalyst for the synthesis of polyhydroquinolines and Hantzsch 1,4-dihydropyridines under solvent-free conditions J. Mol. Catal. Chem. 382 99

    Article  CAS  Google Scholar 

  8. Saha M 2011 Palladium0 nanoparticles: an efficient catalyst for the one-pot synthesis of polyhydroquinolines Tetrahedron Lett. 52 4872

  9. Garden S J, Guimarães C R W, Corréa M B, Oliveira C A, Pinto A C and Bicca de Alencastro R 2003 Synthetic and theoretical studies on the reduction of electron withdrawing group conjugated olefins using the Hantzsch 1,4-dihydropyridine Ester. J. Org. Chem. 68 8815

    Article  CAS  PubMed  Google Scholar 

  10. Devi Guggilapu S, Kumar Prajapti S, Nagarsenkar A, Lalita G, Vegi G M N and Nagendra Babu B 2016 MoO2Cl2 catalyzed efficient synthesis of functionalized 3,4-dihydropyrimidin-21 H -ones/thiones and polyhydroquinolines: recyclability, fluorescence and biological studies New J. Chem. 40 838

    Article  Google Scholar 

  11. Yasar S, Corrada M, Brookmeyer R and Kawas C 2005 Calcium channel blockers and risk of AD: the Baltimore Longitudinal Study of Aging Neurobiol. Aging. 26 157

    Article  CAS  PubMed  Google Scholar 

  12. der Lee R, van Pfaffendorf M and van Zwieten P A 2000 The differential time courses of the vasodilator effects of various 14-dihydropyridines in isolated human small arteries are correlated to their lipophilicity J. Hypertens. 18 1677

    Article  PubMed  Google Scholar 

  13. Jiang B, Rajale T, Wever W, Tu S J and Li G 2010 Multicomponent Reactions for the Synthesis of Heterocycles Chem. - Asian J. 5 2318

  14. John S E, Gulati S and Shankaraiah N 2021 Recent advances in multi-component reactions and their mechanistic insights: a triennium review Org. Chem. Front. 8 4237

    Article  CAS  Google Scholar 

  15. Shirini F and Abedini M 2013 Application of nanocatalysts in multi-component reactions J. Nanosci. Nanotechnol. 13 4838

    Article  CAS  PubMed  Google Scholar 

  16. Bhaskaruni S V H S, Maddila S, Gangu K K and Jonnalagadda S B 2020 A review on multi-component green synthesis of N-containing heterocycles using mixed oxides as heterogeneous catalysts Arab. J. Chem. 13 1142

    Article  CAS  Google Scholar 

  17. Neto B A D, Rocha R O and Rodrigues M O 2022 Catalytic approaches to multicomponent reactions: a critical review and perspectives on the roles of catalysis Molecules 27 132

    Article  CAS  Google Scholar 

  18. Kar S, Sanderson H, Roy K, Benfenati E and Leszczynski J 2022 Green chemistry in the synthesis of pharmaceuticals Chem. Rev. 122 3637

    Article  CAS  PubMed  Google Scholar 

  19. Chen M N, Mo L P, Cui Z S and Zhang Z-H 2019 Magnetic nanocatalysts: Synthesis and application in multicomponent reactions Curr. Opin. Green. Sustain. Chem. 15 27

    Article  Google Scholar 

  20. José Climent M, Corma A and Iborra S 2012 Homogeneous and heterogeneous catalysts for multicomponent reactions RSC Adv. 2 16

    Article  Google Scholar 

  21. Wang D and Astruc D 2014 Fast-growing field of magnetically recyclable nanocatalysts Chem. Rev. 114 6949

    Article  CAS  PubMed  Google Scholar 

  22. Kumar P, Tomar V, Kumar D, Joshi R and Nemiwal M 2022 Magnetically active iron oxide nanoparticles for catalysis of organic transformations: A review Tetrahedron 106–107 132641

    Article  Google Scholar 

  23. Mondal J, Sen T and Bhaumik A 2012 Fe3O4@mesoporous SBA-15: a robust and magnetically recoverable catalyst for one-pot synthesis of 34-dihydropyrimidin-21H-ones via the Biginelli reaction Dalton. Trans. 41 6173

    Article  CAS  PubMed  Google Scholar 

  24. Fan G, Li F, Evans DG and Duan X 2014 Catalytic applications of layered double hydroxides: recent advances and perspectives Chem. Soc. Rev. 43 7040

    Article  CAS  PubMed  Google Scholar 

  25. Shinde G and Thakur J 2022 Magnetically recyclable Ag@Fe2O3 core-shell nanostructured catalyst for one-pot synthesis of 2-aryl benzimidazole and benzothiazole Curr Organocatal. 09 237

    Article  Google Scholar 

  26. Banerjee B 2019 Ultrasound and nano-catalysts: an ideal and sustainable combination to carry out diverse organic transformations ChemistrySelect 4 2484

    Article  CAS  Google Scholar 

  27. Zangade S and Patil P 2020 A review on solvent-free methods in organic synthesis Curr. Org. Chem. 23 2295

    Article  Google Scholar 

  28. Kaboudin B, Kazemi F and Habibi F 2015 Fe3O4@MgO nanoparticles as an efficient recyclable catalyst for the synthesis of phosphoroamidates via the Atherton–Todd reaction Tetrahedron Lett. 56 6364

  29. Salem A N M, Ahmed M A and El-Shahat M F 2016 Selective adsorption of amaranth dye on Fe3O4/MgO nanoparticles J. Mol. Liq. 219 780

    Article  CAS  Google Scholar 

  30. Tan D, Jin J, Guo C, Dhanjai and Chen J 2020 Magnetic magnesium oxide composites for rapid removal of polycyclic aromatic hydrocarbons and cadmium ions from water Environ. Chem. 17 479

  31. Peng H, Wang X, Hu C, Hu J and Tian X 2016 A simple approach for the synthesis of bi-functional Fe3O4@MgO core–shell nanoparticles with magnetic-microwave to heat responsive properties New J. Chem. 40 7911

    Article  CAS  Google Scholar 

  32. Ahankar H, Ramazani A and Joo S W 2016 Magnetic nickel ferrite nanoparticles as an efficient catalyst for the preparation of polyhydroquinoline derivatives under microwave irradiation in solvent-free conditions Res. Chem. Intermed. 42 2487

    Article  CAS  Google Scholar 

  33. Nikoorazm M and Erfani Z 2019 Core–shell nanostructure Fe3O4@MCM-41@Cu-P2C as a highly efficient and recoverable nanocatalyst for the synthesis of polyhydroquinoline 5-substituted 1H-tetrazoles and sulfides Chem. Phys. Lett. 737 136784

    Article  CAS  Google Scholar 

  34. Shaker M and Beni A S 2021 Cu@SB-MCM-41 composite as an efficient and recyclable nanocatalyst for the synthesis of polyhydroquinoline derivatives via unsymmetrical Hantzsch reaction J. Porous. Mater. 28 435

    Article  CAS  Google Scholar 

  35. Tanna J A, Chaudhary R G, Sonkusare V N and Juneja H D 2016 CuO nanoparticles: synthesis characterization and reusable catalyst for polyhydroquinoline derivatives under ultrasonication J. Chin. Adv. Mater. Soc. 4 110

    Article  CAS  Google Scholar 

  36. Parhad A, Aute D, Gadhave A and Uphade B 2021 Gallium oxide (Ga2O3): an efficient heterogeneous nanocatalyst for one pot, multi-component synthesis of polyhydroquinolines Polycycl. Aromat. Compd. 42 5809

    Article  Google Scholar 

  37. Nosrati A, Amirnejat S and Javanshir S 2021 Preparation antibacterial activity and catalytic application of magnetic graphene oxide-fucoidan in the synthesis of 14-dihydropyridines and polyhydroquinolines ChemistryOpen 10 1186

  38. Ghorbani C A, Tahmasbi B and Moradi Z 2017 S-Benzylisothiourea complex of palladium on magnetic nanoparticles: A highly efficient and reusable nanocatalyst for synthesis of polyhydroquinolines and Suzuki reaction: Pd-SBTU@Fe3O4 applied as organometal nanocatalyst Appl. Organomet. Chem. 31 e3665

    Article  Google Scholar 

  39. Hajjami M and Tahmasbi B 2015 Synthesis and characterization of Glucosulfonic acid supported on Fe3O4 nanoparticles as novel and magnetically recoverable nanocatalyst and its application in the synthesis of polyhydroquinoline and 23- dihydroquinazolin-41H-one Derivatives RSC Adv. 05 59194

  40. Dhanunjayarao A V, Surasani R, Vykunteswararao B P, Bhaskarkumar T, Srikanth B, Jogdand N R, et al. 2016 Sulfonic acid–functionalized Wang resin (Wang-OSO3H) as polymeric acidic catalyst for the ecofriendly multicomponent synthesis of polyhydroquinolines via Hantzsch condensation Synth. Commun. 46 1519

    Article  CAS  Google Scholar 

  41. Ranjbar-Karimi R, Hashemi-Uderji S and Bazmandegan-Shamili A 2011 MgO nanoparticles as a recyclable heterogeneous catalyst for the synthesis of polyhydroquinoline derivatives under solvent free conditions Chin. J. Chem. 29 1624

    Article  CAS  Google Scholar 

  42. Sheibani H, Seifi M and Bazgir A 2009 Three-component synthesis of pyrimidine and pyrimidinone derivatives in the presence of high-surface-area MgO a highly effective heterogeneous base catalyst Synth. Commun. 39 1055

    Article  CAS  Google Scholar 

  43. Kaboudin B, Kazemi F and Habibi F 2015 MgO-coated-Fe3O4 nanoparticles as a magnetically recoverable and reusable catalyst for the synthesis of 1-hydroxyphosphonates J. Iran. Chem. Soc. 12 469

    Article  CAS  Google Scholar 

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Acknowledgements

The authors acknowledge SAIF, IIT, Mumbai, SAIF, IIT, Madras, CSMCRI, Bhavnagar, STIC, Cochin for extending instrumental support.

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Correspondence to Jyotsna Thakur.

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Shinde, G., Thakur, J. Core-shell structured Fe3O4@MgO: magnetically recyclable nanocatalyst for one-pot synthesis of polyhydroquinoline derivatives under solvent-free conditions. J Chem Sci 135, 14 (2023). https://doi.org/10.1007/s12039-023-02134-9

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  • DOI: https://doi.org/10.1007/s12039-023-02134-9

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