The use of recyclable magnetic nanocatalyst Fe3O4@SiO2-(CH2)3-Pyridine-2-(1H)-tetrazole-Cu(II) in the synthesis of bis-coumarin derivatives under green conditions

محورهای موضوعی : Iranian Journal of Catalysis

Ali Oji Moghanlou ¹ , Mohammadali Pourshahi ² , Siamak Atabak ³ , Nayer Mohammadian Tarighi ⁴

1 - Department of Chemistry, Ardabil Branch, Islamic Azad University, Ardabil, Iran, 56157-31567
2 - Department of Chemistry, Ardabil Branch, Islamic Azad University, Ardabil, Iran, 56157-31567
3 - Department of Chemistry, Ardabil Branch, Islamic Azad University, Ardabil, Iran, 56157-31567
4 - Department of Chemistry, Ardabil Branch, Islamic Azad University, Ardabil, Iran, 56157-31567

تاریخ دریافت : 1402/01/06 تاریخ پذیرش : 1402/04/08 تاریخ انتشار : 1402/04/10

کلید واژه: aldehyde, coumarin, Magnetic nanocatalyst, Bis-coumarin, Copper catalyst,

چکیده مقاله :

In the present work, first, magnetic nanoparticles (MNP) were synthesized, and a layer of silica was placed on the magnetite nanoparticles through the reaction with TEOS. Next, the pyridine-2-(1H)-tetrazole ligand was fixed on the core-shell magnetite nanoparticles, and finally, the nanocatalyst copper complex was synthesized. The synthesized copper (II) complex of magnetic nanocatalyst was identified through different analyses such as FT-IR, SEM, EDX, XRD, VSM, BET, and atomic absorption. After characterizing the nanocatalyst Fe3O4@SiO2-(CH2)3-Pyridine-2-(1H)-tetrazole-Cu(II), by applying this catalyst in the reaction of benzaldehyde with 4-hydroxycoumarin, the reaction conditions such as solvent type, reaction temperature and The amount of catalyst was optimized. Ethanol was chosen as the optimal solvent as an environmentally friendly solvent. The recycling cycle of the magnetic catalyst was also studied, and the slight decrease in the catalyst's efficiency after six times reactions indicates the high efficiency of this nanocatalyst in the synthesis reaction of bis-coumarin derivatives as a green catalyst.

منابع و مأخذ:

[1] Y. Wang, X. Wang, M. Antonietti, Polymeric graphitic carbon nitride as a heterogeneous organocatalyst: from photochemistry to multipurpose catalysis to sustainable chemistry, Angew. Chem. Inter. Edit., 51 (2012) 68-89.

[2] M. Ghobadi, M. Kargar Razi, R. Javahershenas, M. Kazemi, Nanomagnetic reusable catalysts in organic synthesis, Synth. Commun., 51 (2021) 647-669.

[3] W. Wu, Q. He, C. Jiang, Magnetic Iron Oxide Nanoparticles: Synthesis and Surface Functionalization Strategies, Nanoscale Res. Lett., 3 (2008) 397.

[4] A.K. Gupta, M. Gupta, Synthesis and surface engineering of iron oxide nanoparticles for biomedical applications, Biomaterials, 26 (2005) 3995-4021.

[5] C. Klein, Hurlburt jr. CS “Manual of Mineralogy”, in, New York, John Wiley and Sons, Inc, 1993.

[6] S. Shylesh, V. Schünemann, W.R. Thiel, Magnetically Separable Nanocatalysts: Bridges between Homogeneous and Heterogeneous Catalysis, Angew. Chem. Inter. Edit., 49 (2010) 3428-3459.

[7] A.S. Arbab, L.A. Bashaw, B.R. Miller, E.K. Jordan, B.K. Lewis, H. Kalish, J.A. Frank, Characterization of biophysical and metabolic properties of cells labeled with superparamagnetic iron oxide nanoparticles and transfection agent for cellular MR imaging, Radiology, 229 (2003) 838-846.

[8] P. Reimer, R. Weissleder, [Development and experimental use of receptor-specific MR contrast media], Der Radiologe, 36 (1996) 153-163.

[9] M. Esmaeilpour, A.R. Sardarian, J. Javidi, Synthesis and characterization of Schiff base complex of Pd (II) supported on superparamagnetic Fe3O4@ SiO2 nanoparticles and its application as an efficient copper-and phosphine ligand-free recyclable catalyst for Sonogashira–Hagihara coupling reactions, J. Organometal. Chem., 749 (2014) 233-240.

[10] M. Esmaeilpour, J. Javidi, F.N. Dodeji, M.M. Abarghoui, Facile synthesis of 1-and 5-substituted 1H-tetrazoles catalyzed by recyclable ligand complex of copper (II) supported on superparamagnetic Fe3O4@ SiO2 nanoparticles, J. Mol. Catal. A: Chem., 393 (2014) 18-29.

[11] M. Sarkheil, M. Lashanizadegan, M. Ghiasi, High catalytic activity of magnetic Fe3O4@ SiO2-Schiff base-Co (II) nanocatalyst for aerobic oxidation of alkenes and alcohols and DFT study, J. Mol. Struct., 1179 (2019) 278-288.

[12] M. Rezaei, K. Azizi, K. Amani, Copper–birhodanine complex immobilized on Fe3O4 nanoparticles: DFT studies and heterogeneous catalytic applications in the synthesis of propargylamines in aqueous medium, Appl. Organometal. Chem., 32 (2018) e4120.

[13] L. Vahabi, P.R. Ranjbar, F. Davar, Cladosporium protease/doxorubicin decorated Fe3O4@ SiO2 nanocomposite: An efficient nanoparticle for drug delivery and combating breast cancer, J. Drug Deliv. Sci. Tech., 80 (2023) 104144.

[14] A.-H. Lu, E.L. Salabas, F. Schüth, Magnetic Nanoparticles: Synthesis, Protection, Functionalization, and Application, Angew. Chem. Inter. Edit., 46 (2007) 1222-1244.

[15] G. Huang, C.-H. Lu, H.-H. Yang, Chapter 3 - Magnetic Nanomaterials for Magnetic Bioanalysis, in: X. Wang, X. Chen (Eds.) Novel Nanomaterials for Biomedical, Environmental and Energy Applications, Elsevier, 2019, pp. 89-109.

[16] G. Gnanaprakash, S. Mahadevan, T. Jayakumar, P. Kalyanasundaram, J. Philip, B. Raj, Effect of initial pH and temperature of iron salt solutions on formation of magnetite nanoparticles, Mater. Chem. Physic., 103 (2007) 168-175.

[17] A. Khalid, R. Ahmed, M. Taha, T. Soliman, Fe3O4 nanoparticles and Fe3O4@ SiO2 core-shell: synthesize, structural, morphological, linear, and nonlinear optical properties, J. Alloy. Comp., 947 (2023) 169639.

[18] B.K. Paul, S.P. Moulik, Uses and applications of microemulsions, Current Science, 80 (2001) 990-1001.

[19] C. Graf, D.L. Vossen, A. Imhof, A. van Blaaderen, A general method to coat colloidal particles with silica, Langmuir, 19 (2003) 6693-6700.

[20] M. Mohapatra, S. Anand, Synthesis and applications of nano-structured iron oxides/hydroxides–a review, International J. Eng., Sci. Tech., 2 (2010).

[21] S. Giri, S. Samanta, S. Maji, S. Ganguli, A. Bhaumik, Magnetic properties of α-Fe2O3 nanoparticle synthesized by a new hydrothermal method, J. Magnet. Magnet. Mater, 285 (2005) 296-302.

[22] Z. Jing, S. Wu, Synthesis and characterization of monodisperse hematite nanoparticles modified by surfactants via hydrothermal approach, Mater. Lett., 58 (2004) 3637-3640.

[23] D. Wang, D. Astruc, Fast-Growing Field of Magnetically Recyclable Nanocatalysts, Chem. Rev., 114 (2014) 6949-6985.

[24] Z. Du, W. Zhou, L. Bai, F. Wang, J.-X. Wang, In Situ Generation of Palladium Nanoparticles: Reusable, Ligand-Free Heck Reaction in PEG-400 Assisted by Focused Microwave Irradiation, Synlett, 2011 (2011) 369-372.

[25] B.B. Shaik, N.K. Katari, P. Seboletswe, R. Gundla, N.D. Kushwaha, V. Kumar, P. Singh, R. Karpoormath, M.D. Bala, Recent Literature Review on Coumarin Hybrids as Potential Anticancer Agents, Anti-Cancer Agents in Medicinal Chemistry (Formerly Current Medicinal Chemistry-Anti-Cancer Agents), 23 (2023) 142-163.

[26] P. Teli, A. Sethiya, S. Agarwal, An insight view on synthetic protocol, mechanistic and biological aspects of biscoumarin derivatives, ChemistrySelect, 4 (2019) 13772-13787.

[27] S. Zeinali, L.Z. Fekri, M. Nikpassand, R.S. Varma, Greener Syntheses of Coumarin Derivatives Using Magnetic Nanocatalysts: Recent Advances, Topics in Current Chemistry, 381 (2023) 1.

[28] F. Borges, F. Roleira, N. Milhazes, L. Santana, E. Uriarte, Simple coumarins and analogues in medicinal chemistry: occurrence, synthesis and biological activity, Current medicinal chemistry, 12 (2005) 887-916.

[29] N.O. Mahmoodi, F. Ghanbari Pirbasti, Z. Jalalifard, Recent advances in the synthesis of biscoumarin derivatives, J. Chin. Chem. Soc., 65 (2018) 383-394.

[30] K. Parvanak Boroujeni, P. Ghasemi, Z. Rafienia, Synthesis of biscoumarin derivatives using poly (4-vinylpyridine)-supported dual acidic ionic liquid as a heterogeneous catalyst, Monatshefte für Chemie-Chemical Monthly, 145 (2014) 1023-1026.

[31] D.S. Reddy, M. Kongot, V. Singh, M.A. Siddiquee, R. Patel, N.K. Singhal, F. Avecilla, A. Kumar, Biscoumarin–pyrimidine conjugates as potent anticancer agents and binding mechanism of hit candidate with human serum albumin, Archiv der Pharmazie, 354 (2021) 2000181.

[32] N.O. Mahmoodi, Z. Jalalifard, G.P. Fathanbari, Green synthesis of bis‐coumarin derivatives using Fe (SD) 3 as a catalyst and investigation of their biological activities, J. Chin. Chem. Soc., 67 (2020) 172-182.

[33] M. Faisal, F.A. Larik, A. Saeed, A highly promising approach for the one-pot synthesis of biscoumarins using HY zeolite as recyclable and green catalyst, J. Porous Mater., 26 (2019) 455-466.

[34] P. Li, R. Su, D. Zhang, M. Han, Y. Zhao, L. Ma, H. Zhang, T. Yu, Carbazole-functionalized V-shaped bis-coumarin derivatives as organic luminescent materials, Synthetic Metals, 287 (2022) 117069.

[35] T. Schalekamp, B.P. Brassé, J.F. Roijers, Y. Chahid, J.H. van Geest‐Daalderop, H. de Vries‐Goldschmeding, E.M. van Wijk, A.C. Egberts, A. de Boer, VKORC1 and CYP2C9 genotypes and acenocoumarol anticoagulation status: interaction between both genotypes affects overanticoagulation, Clinical Pharmacology & Therapeutics, 80 (2006) 13-22.

[36] E. Zarenezhad, M.N. Montazer, M. Tabatabaee, C. Irajie, A. Iraji, New solid phase methodology for the synthesis of biscoumarin derivatives: experimental and in silico approaches, BMC Chemistry, 16 (2022) 53.

[37] W.L.F. Armarego, C.L.L. Chai, Purification of laboratory chemicals, 5^th ed., Butterworth-Heinemann, Burlington, 2003.

[38] Y. Mansoori, B. Koohi-Zargar, H. Shekaari, M.R. Zamanloo, G.H. Imanzadeh, Polyamides with pendant 1,3,4-oxadiazole and pyridine moieties, Chin. J. Polymer Sci., 30 (2012) 112-121.

[39] L. Ciccotti, L.A.S. do Vale, T.L.R. Hewer, R.S. Freire, Fe3O4@TiO2 preparation and catalytic activity in heterogeneous photocatalytic and ozonation processes, Catal. Sci. Tech., 5 (2015) 1143-1152.

[40] S. Wang, K. Wang, C. Dai, H. Shi, J. Li, Adsorption of Pb2+ on amino-functionalized core–shell magnetic mesoporous SBA-15 silica composite, Chem. Eng. J., 262 (2015) 897-903.

[41] M. Nasrollahzadeh, Z. Issaabadi, S.M. Sajadi, Fe 3 O 4@ SiO 2 nanoparticle supported ionic liquid for green synthesis of antibacterially active 1-carbamoyl-1-phenylureas in water, RSC adv., 8 (2018) 27631-27644.

[42] H. Mehrabi, H. Abusaidi, Synthesis of biscoumarin and 3, 4-dihydropyrano [c] chromene derivatives catalysed by sodium dodecyl sulfate (SDS) in neat water, J. Iran. Chem. Soc., 7 (2010) 890-894.

[43] P. Teli, A. Sethiya, S. Agarwal, Black yet green: A heterogenous carbon-based acid catalyst for the synthesis of biscyclic derivatives under eco-friendly conditions, Res. Chem. Intermed., 48 (2022) 731-750.

[44] A. Shamsaddini, E. Sheikhhosseini, Synthesis of 3, 3-arylidene bis (4-hydroxycoumarin) catalyzed by p-dodecylbenzenesulfonic acid (DBSA) in aqueous media and microwave irradiation, Inter. J. Org. Chem., 4 (2014) 135-141.

[45] A.D. Gupta, S. Samanta, R. Mondal, A.K. Mallik, A Convenient, Eco-friendly, and Efficient Method for Synthesis of 3, 3'-Arylmethylene-bis-4-hydroxycoumarins, Bullet. Korean Chem. Soc., 33 (2012) 4239-4242.

[46] N. Iravani, M. Keshavarz, M. Mousavi, M. Baghernejad, Melamine trisulfonic acid: An efficient and recyclable solid acid catalyst for the green synthesis of Biscoumarin derivatives, Iran. J. Catal., 5 (2015) 65-71.

[47] S. Zahiri, M. Mokhtary, Bi (NO3) 3· 5H2O: An efficient catalyst for one-pot synthesis of 3-((aryl)(diethylamino) methyl)-4-hydroxy-2H-chromen-2-ones and biscoumarin derivatives, J. Taibah Uni. Sci., 9 (2015) 89-94.

[48] Z. Zare-Akbari, L. Edjali, M. Eshaghi, Synthesis of Novel Bis-Coumarin Derivatives as Potential Acetylcholinesterase Inhibitors: An In Vitro, Molecular Docking, and Molecular Dynamics Simulations Study, Pharmaceutical and Biomedical Research, 8 (2022) 131-142.

[49] Z.M. Mohammadi, N. Mahmoodi, Nano TiO2@ KSF as a high-efficient catalyst for solvent-free synthesis of Biscoumarin derivatives, Int. J. Nano Dimens 7(2) (2016) 174-180.

[50] B. Kharrngi, E.D. Dhar, G. Basumatary, D. Das, R.C. Deka, A.K. Yadav, G. Bez, Developing a highly potent anthelmintic: study of catalytic application of l-proline derived aminothiourea in rapid synthesis of biscoumarins and their in vitro anthelmintic essay, J. Chem. Sci., 133 (2021) 16.

[51] J. Albadi, A. Mansournezhad, S. Salehnasab, Green synthesis of biscoumarin derivatives catalyzed by recyclable CuO–CeO2 nanocomposite catalyst in water, Res. Chem. Intermed., 41 (2015) 5713-5721.