Synthesis of a salen complex supported on cobalt ferrite-hydroxyapatite magnetic nanoparticles and its application in the preparation of spirooxindole compounds
Subject Areas : Synthesis and Characterization of NanostructuresMohammad Ali Nasseri 1 * , Batol Zakerinasab 2 , Azam Habibollahi 3
1 - Department of Chemistry, College of Sciences, University of Birjand, Birjand, Iran.
2 - Department of Chemistry, College of Sciences, University of Birjand, Birjand, Iran.
3 - epartment of Chemistry, College of Sciences, University of Birjand, Birjand, Iran.
Keywords: Catalyst, Salen complex, Magnetic nanoparticles, Nanocomplexes, Spirooxindoles.,
Abstract :
In this study, considering the importance of nanocatalysts in organic reactions, a copper salen complex supported on cobalt ferrite–hydroxyapatite magnetic nanoparticles(CoFe₂O₄@HAP@Cu Salen Complex) was synthesized and characterized using various techniques including FT-IR, SEM, ICP, XRD, etc. The activity of the catalyst in a multicomponent reaction was investigated for the synthesis of spirooxindole derivatives, and high-yield products were prepared. The absence of toxic solvents, easy recycling and reusability of the catalyst, and no formation of by-products are the advantages of this method.
[1] A. Soroceanu, A. Bargan, Advanced and biomedical applications of Schiff-base ligands and their metal complexes: A review, Crystals 12 (2022) 1436.
[2] B.M.L. Dioos, P.A. Jacobs, Microwave-assisted Cr (salen)-catalysed asymmetric ring opening of epoxides, J. Catal. 235 (2005) 428–430.
[3] N. Turan, H. Seymen, B. Gündüz, K. Buldurun, N. Çolak, Synthesis, characterization of Schiff base and its metal complexes and investigation of their electronic and photonic properties, Opt. Mater. (Amst). 148 (2024) 114802.
[4] A. Prakash, D. Adhikari, Application of Schiff bases and their metal complexes-A Review, Int. J. Chem. Tech. Res 3 (2011) 1891–1896.
[5] I.R. Pathan, M.K. Patel, A comprehensive review on the synthesis and applications of Schiff base ligand and metal complexes: A comparative study of conventional heating, microwave heating, and sonochemical methods, Inorg. Chem. Commun. 158 (2023) 111464.
[6] F. Nworie, F. Nwabue, N. Elom, S. Eluu, Schiff bases and schiff base metal complexes: from syntheses to applications, J. Basic Appl. Res. Biomed. 2 (2025) 295–305.
[7] M. Kazemnejadi, M.A. Nasseri, S. Sheikh, Z. Rezazadeh, S.A.A. Gol, Fe 3 O 4@ Sap/Cu (ii): an efficient magnetically recoverable green nanocatalyst for the preparation of acridine and quinazoline derivatives in aqueous media at room temperature, RSC Adv. 11 (2021) 15989–16003.
[8] M.A. Nasseri, M. Shahabi, A. Allahresani, A novel, efficient and magnetically recyclable Cu–Ni bimetallic alloy nanoparticle as a highly active bifunctional catalyst for Pd-free Sonogashira and C–N cross-coupling reactions: A combined theoretical and experimental study, RSC Adv. 13 (2023) 22158–22171.
[9] K. Sangeetha, M. Ashok, E.K. Girija, Development of multifunctional cobalt ferrite/hydroxyapatite nanocomposites by microwave assisted wet precipitation method: A promising platform for synergistic chemo-hyperthermia therapy, Ceram. Int. 45 (2019) 12860–12869.
[10] M. Rastgordani, J. Zolgharnein, Magnetic CoFe2O4@ HAp-GQDs nanocomposites for removal of Brilliant crysel blue dye using FCCD optimization and adsorption characterization, Mater. Sci. Eng. B 290 (2023) 116290.
[11] X. Xiao, L. Yang, D. Zhou, J. Zhou, Y. Tian, C. Song, C. Liu, Magnetic γ-Fe2O3/Fe-doped hydroxyapatite nanostructures as high-efficiency cadmium adsorbents, Colloids Surfaces A Physicochem. Eng. Asp. 555 (2018) 548–557.
[12] A. Saffar-Teluri, Direct covalent attachment of Mn (III) salophen complex to the hydroxyapatite-encapsulated γ-Fe 2 O 3 nanocrystallites: an efficient magnetic and reusable catalyst for oxidation of alcohols, RSC Adv. 5 (2015) 70577–70585.
[13] N. Razavi, B. Akhlaghinia, Hydroxyapatite nanoparticles (HAP NPs): a green and efficient heterogeneous catalyst for three-component one-pot synthesis of 2, 3-dihydroquinazolin-4 (1 H)-one derivatives in aqueous media, New J. Chem. 40 (2016) 447–457.
[14] F. Mohandes, M. Salavati-Niasari, Particle size and shape modification of hydroxyapatite nanostructures synthesized via a complexing agent-assisted route, Mater. Sci. Eng. C 40 (2014) 288–298.
[15] E. Kabir, M. Uzzaman, A review on biological and medicinal impact of heterocyclic compounds, Results Chem. 4 (2022) 100606.
[16] A.M. Escobar, G. Blustein, R. Luque, G.P. Romanelli, Recent applications of heteropolyacids and related compounds in heterocycle synthesis. Contributions between 2010 and 2020, Catalysts 11 (2021) 291.
[17] F.M. Alshareef, J.S. Algethami, M.A.M. Alhamami, E.H. Alosaimi, H.M. Al-Saidi, S. Khan, Recent Advancement in Organic Fluorescent and Colorimetric Chemosensors for the Detection of Al3+ Ions: A Review (2019-2024), J. Environ. Chem. Eng. (2024) 114110.
[18] A. Kumar, A. Mishra, ROLE OF HETEROCYCLIC COMPOUNDS IN PHARMACEUTICALS AND MEDICINES., J. Exp. Zool. India 26 (2023).
[19] H. Hassani, B. Zakerinasab, M.A. Nasseri, M. Shavakandi, The preparation, characterization and application of COOH grafting on ferrite–silica nanoparticles, RSC Adv. 6 (2016) 17560–17566.
[20] M.A. Nasseri, F. Ahrari, B. Zakerinasab, A green biosynthesis of NiO nanoparticles using aqueous extract of Tamarix serotina and their characterization and application, Appl. Organomet. Chem. 30 (2016) 978–984.
[21] M.A. Nasseri, B. Zakerinasab, S. Kamayestani, Catalytic activity of reusable Mn (II) salen complex immobilized on nano silicagel in the oxidation of sulfides, J. Iran. Chem. Soc. 12 (2015) 1457–1463.
[22] M.A. Nasseri, B. Zakerinasab, M.M. Samieadel, Sulfamic acid supported on Fe 3 O 4@ SiO 2 superpara magnetic nanoparticles as a recyclable heterogeneous catalyst for the synthesis of quinolines, RSC Adv. 4 (2014) 41753–41762.
[23] M.A. Nasseri, B. Zakerinasab, Sulfuric acid-modified poly (ethylene glycol): an efficient, biodegradable, and reusable polymeric catalyst for synthesis of spiro oxindole derivatives in aqueous medium, Res. Chem. Intermed. 41 (2015) 5261–5270.
[24] M.A. Nasseri, B. Zakerinasab, S. Kamayestani, Proficient procedure for preparation of quinoline derivatives catalyzed by NbCl5 in glycerol as green solvent, J. Appl. Chem. 2015 (2015) 743094.
[25] M.A. Nasseri, F. Kamali, B. Zakerinasab, Catalytic activity of reusable nickel oxide nanoparticles in the synthesis of spirooxindoles, RSC Adv. 5 (2015) 26517–26520.
[26] S. Sheikh, M.A. Nasseri, A. Allahresani, R.S. Varma, Copper adorned magnetic nanoparticles as a heterogeneous catalyst for Sonogashira coupling reaction in aqueous media, Sci. Rep. 12 (2022) 17986.
[27] S. Sheikh, M.A. Nasseri, M. Chahkandi, A. Allahresani, O. Reiser, Functionalized magnetic PAMAM dendrimer as an efficient nanocatalyst for a new synthetic strategy of xanthene pigments, J. Hazard. Mater. 400 (2020) 122985.
[28] M.A. Nasseri, K. Hemmat, A. Allahresani, E. Hamidi‐Hajiabadi, CoFe2O4@ SiO2@ Co (III) salen complex nanoparticle as a green and efficient magnetic nanocatalyst for the oxidation of benzyl alcohols by molecular O2, Appl. Organomet. Chem. 33 (2019) e4809.
[29] C. García, C. García, C. Paucar, Controlling morphology of hydroxyapatite nanoparticles through hydrothermal microemulsion chemical synthesis, Inorg. Chem. Commun. 20 (2012) 90–92.
[30] F. Foroughi, S.A. Hassanzadeh-Tabrizi, J. Amighian, A. Saffar-Teluri, A designed magnetic CoFe2O4–hydroxyapatite core–shell nanocomposite for Zn (II) removal with high efficiency, Ceram. Int. 41 (2015) 6844–6850.