The First Pyrazolium-Based Ionic Liquid Containing Phosphotungstic Acid Immobilized on CuFe2O4@SiO2: A Recyclable Organic-Inorganic Nanohybrid Catalyst for the Synthesis of Polyhydroquinolines

Document Type : Research Article

Authors

1 Department of Chemistry, Mashhad Branch, Islamic Azad University, Mashhad, I.R. IRAN

2 Young Researchers and Elite Club, Mashhad Branch, Islamic Azad University, Mashhad, I.R. IRAN

Abstract

A new magnetically separable organic-inorganic nanohybrid catalyst denoted as CuFe2O4@SiO2@C3-Pyrazole-C4SO3-H2PW was successfully prepared by grafting of a functionalized ionic liquid containing a pyrazolium cation with a phosphotungstic counter-anion H2PW12O40¯ (H2PW) on silica-coated copper ferrite magnetic nanoparticles (CuFe2O4@SiO2). The prepared catalyst was fully characterized using scanning electron microscopy, transmission electron microscopy, energy-dispersive X-ray analysis, inductively coupled plasma optical emission spectrometry, Fourier transform infrared spectroscopy, and vibrating sample magnetometry. The catalytic activity of CuFe2O4@SiO2@C3-Pyrazole-C4SO3-H2PW as a novel heterogeneous catalyst was probed in the synthesis of polyhydroquinolines by one-pot condensation of dimedone, an aromatic aldehyde, ammonium acetate, and ethyl acetoacetate. The results demonstrated a significant catalytic performance of the catalyst for this transformation under solvent-free conditions, giving high yields of the products over short reaction time. Also, the magnetic nanocatalyst could be easily recovered from the reaction mixture and reused many times with no significant loss of its catalytic activity.

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References

[1] Sarma P., Dutta A.K., Borah R., Design and Exploration of -SO3H Group Functionalized Brønsted Acidic Ionic Liquids (BAILs) as Task-Specific Catalytic Systems for Organic Reactions: A Review of Literature, Catal. Surv. Asia, 21(2): 70-93 (2017).
[2] Vekariya R.L., A Review of Ionic Liquids: Applications Towards Catalytic Organic Transformations, J. Mol. Liq., 227: 44-60 (2017).
[3] Greaves T.L., Drummond C.J., Protic Ionic Liquids: Evolving Structure-Property Relationships and Expanding Applications, Chem. Rev., 115(20): 11379-11448 (2015).
[4] Davoodnia A., Khojastehnezhad A., Bakavoli M., Tavakoli-Hoseini N., SO3H-Functionalized Ionic Liquids: Green, Efficient and Reusable Catalysts for the Facile Dehydration of Aldoximes into Nitriles, Chin. J. Chem., 29(5): 978-982 (2011).
[5] Tavakoli-Hoseini N., Heravi M.M., Bamoharram F.F., Davoodnia A., Ghassemzadeh M., An Unexpected Tetracyclic Product Isolated During the Synthesis of Biscoumarins Catalyzed by [MIM(CH2)4SO3H] [HSO4]: Characterization and X-ray Crystal Structure of 7-(2-Hydroxy-4-oxo-4H-chromen-3-yl)-6H,7H-chromeno[4,3-b]chromen-6-one, J. Mol. Liq., 163(3): 122-127 (2011).
[6] Dehghan M., Davoodnia A., Bozorgmehr M.R., Bamoharram F.F., Evaluation of Catalytic Activity of Two Newly Prepared Functionalized Sulfonic Acids Ionic Liquids in the Synthesis of Carbamatoalkyl Naphthols Under Mild Conditions, Russ. J. Gen. Chem., 87(2): 311-315 (2017).
[7] Khaligh N.G., Introduction 1,1′-butylenebis(3-methyl-3H-imidazol-1-ium) Hydrogen Sulfate as an Efficient Binuclear Brönsted Acidic Ionic Liquid for Three-Component and One-Pot Synthesis of Benzo[f]indenoquinoline Derivatives, Polycyclic Aromat. Compd., 35(5): 428-438 (2015).
[8] Vahdat S.M., Zolfigol M.A., Baghery S., Straightforward Hantzsch Four- and Three-Component Condensation in the Presence of Triphenyl(propyl-3-sulfonyl) phosphoniumtrifluoromethanesulfonate [TPPSP]OTf as a Reusable and Green Mild Ionic Liquid Catalyst, Appl. Organomet. Chem., 30(5): 311-317 (2016).
[9] Wight A.P., Davis E., Design and Preparation of Organic-Inorganic Hybrid Catalysts, Chem. Rev., 102(10): 3589-3614 (2002).
[10] Bhanja P., Bhaumik A., Organic-Inorganic Hybrid Metal Phosphonates as Recyclable Heterogeneous Catalysts, Chem. Cat. Chem., 8(9): 1607-1616 (2016).
[11] Eshghi H., Khojastehnezhad A., Moeinpour F., Rezaeian S., Bakavoli M., Teymouri M., Rostami A., Haghbeen K., Nanomagnetic Organic-Inorganic Hybrid (Fe@Si-Gu-Prs): A Novel Magnetically Green Catalyst for the Synthesis of Tetrahydropyridine Derivatives at Room Temperature Under Solvent-Free Conditions, Tetrahedron, 71(3): 436-444 (2015).
[12] Ghahremanzadeh R., Rashid Z., Zarnani A.H., Naeimi H., Inorganic-Organic Hybrid Silica Based Tin Complex as a Novel, Highly Efficient and Recyclable Heterogeneous Catalyst for the One-Pot Preparation of Spirooxindoles in Water, Dalton Trans., 43(42): 15791-15797 (2014).
[13] Wang D., Astruc D., Fast-Growing Field of Magnetically Recyclable Nanocatalysts, Chem. Rev., 114(14): 6949-6985 (2014).
[14] Wu L., Mendoza-Garcia A., Li Q., Sun S., Organic Phase Syntheses of Magnetic Nanoparticles and Their Applications, Chem. Rev., 116(18): 10473-10512 (2016).
[15] Yadegarian S., Davoodnia A., Nakhaei A., Solvent-Free Synthesis of 1,2,4,5-Tetrasubstituted Imidazoles Using Nano Fe3O4@SiO2-OSO3H as a Stable and Magnetically Recyclable Heterogeneous Catalyst, Orient. J. Chem., 31(1): 573-579 (2015).
[16] Ghorbani-Choghamarani A., Tahmasbi B., Noori N., Faryadi S., Pd–S-Methylisothiourea Supported on Magnetic Nanoparticles as an Efficient and Reusable Nanocatalyst for Heck and Suzuki Reactions, C. R. Chim., 20(2): 132-139 (2017).
[17] Pourjavadi A., Hosseini S.H., AghayeeMeibody S.A., Hosseini S.T., Poly(basic ionic liquid) Coated Magnetic Nanoparticles: High-Loaded Supported Basic Ionic Liquid Catalyst, C. R. Chim., 16(10): 906-911 (2013).
[18] Ghorbani-Choghamarani A., Norouzi M., Synthesis and Characterization of Ionic Liquid Immobilized on Magnetic Nanoparticles: A Recyclable Heterogeneous Organocatalyst for the Acetylation of Alcohols, J. Magn. Magn. Mater., 401: 832-840 (2016).
[19] Zolfigol M.A., Ayazi-Nasrabadi R., Baghery S., The First Urea-Based Ionic Liquid-Stabilized Magnetic Nanoparticles: An Efficient Catalyst for the Synthesis of Bis(indolyl)methanes and Pyrano[2,3-d]pyrimidinone Derivatives, Appl. Organomet. Chem., 30(5): 273-281 (2016).
[20] Alinezhad H., Tajbakhsh M., Ghobadi N., Ionic Liquid Immobilized on Fe3O4 Nanoparticles: A Magnetically Recyclable Heterogeneous Catalyst for One-Pot Three-Component Synthesis of 1,8-Dioxodecahydroacridines, Res. Chem. Intermed., 41(12): 9979-9992 (2015).
[21] Safari J., Zarnegar Z., Ni Ion-Containing Immobilized Ionic Liquid on Magnetic Fe3O4 Nanoparticles: An Effective Catalyst for the Heck Reaction, C. R. Chim., 16(9): 821-828 (2013).
[22] Zhang Y., Jiao Q., Zhen B., Wu Q., Li H., Transesterification of Glycerol Trioleate Catalyzed by Basic Ionic Liquids Immobilized on Magnetic Nanoparticles: Influence of Pore Diffusion Effect, Appl. Catal. A: Gen., 453: 327-333 (2013).
[23] Dharma Rao G.B., Nagakalyan S., Prasad G.K., Solvent-Free Synthesis of Polyhydroquinoline Derivatives Employing Mesoporous Vanadium Ion Doped Titania Nanoparticles as a Robust Heterogeneous Catalyst via the Hantzsch Reaction, RSC Adv., 7(6): 3611-3616 (2017).
[24] Goli-Jolodar O., Shirini F., Seddighi, M., Introduction of a Novel Nanosized N-Sulfonated Brönsted Acidic Catalyst for the Promotion of the Synthesis of Polyhydroquinoline Derivatives via Hantzsch Condensation Under Solvent-Free Conditions, RSC Adv., 6(31): 26026-26037 (2016).
[25] Davoodnia A., Khojastehnezhad A., Carbon-Based Solid Acid Catalyzed Synthesis of Polyhydroquinoline Derivatives via Hantzsch Reaction Under Solvent-Free Conditions, J. Chil. Chem. Soc., 57(4): 1385-1387 (2012).
[26] Khashi M., Allameh S., Beyramabadi S.A., Morsali A., Dastmalchian E., Gharib A., BiFeO3 Magnetic Nanoparticles: A Novel, Efficient and Reusable Magnetic Catalyst for the Synthesis of Polyhydroquinoline Derivatives, Iran. J. Chem. Chem. Eng. (IJCCE), 36(3): 45-52 (2017).
[27] Davoodnia A., Khashi M., Tavakoli-Hoseini N., Tetrabutylammonium Hexatungstate [TBA]2[W6O19]: Novel and Reusable Heterogeneous Catalyst for Rapid Solvent-Free Synthesis of Polyhydroquinolines via Unsymmetrical Hantzsch Reaction, Chin. J. Catal., 34(6): 1173-1178 (2013).
[28] Kiasat A.R., Nazari S., Davarpanah, J., β-Cyclodextrin-Polyurethane Polymer: A Neutral and Eco-Friendly Heterogeneous Catalyst for the One-Pot Synthesis of 1,4-Dihydropyridine and Polyhydroquinoline Derivatives via the Hantzsch Reaction Under Solvent-Free Conditions, J. Serb. Chem. Soc., 79(4): 401-409 (2014).
[29] Maleki B., Tayebee R., Kermanian M., Ashrafi S.S., 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(4): 290-297 (2013).
[30] Mohammadi Ziarani G., Badiei A.R., Khaniania Y., Haddadpour M., 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. (IJCCE), 29(2): 1-10 (2010).
[31] Khojastehnezhad A., Moeinpour F., Davoodnia A., PPA-SiO2 Catalyzed Efficient Synthesis of Polyhydroquinoline Derivatives Through Hantzsch Multicomponent Condensation Under Solvent-Free Conditions, Chin. Chem. Lett., 22(7): 807-810 (2011).
[32] Sakram B., Sonyanaik B., Ashok K., Rambabu S., Polyhydroquinolines: 1-Sulfopyridinium Chloride Catalyzed an Efficient One-Pot Multicomponent Synthesis via Hantzsch Condensation Under Solvent-Free Conditions, Res. Chem. Intermed., 42(10): 7651-7658 (2016).
[33] Kidwai M., Chauhan R., Bhatnagar D., Singh A. K., Mishra B., Dey S., Nafion-H®-Catalyzed Synthesis of Polyhydroquinolines via The Hantzsch Multicomponent Reaction, Monatsh. Chem., 143(12): 1675-1680 (2012).
[34] Tajbakhsh M., Alaee E., Alinezhad H., Khanian M., Jahani F., Khaksar S., Rezaee P., Tajbakhsh M., Titanium Dioxide Nanoparticles Catalyzed Synthesis of Hantzsch Esters and Polyhydroquinoline Derivatives, Chin. J. Catal., 33(9): 1517-1522 (2012).
[35] Abdollahi-Alibeik M., Hoseinikhah S.S., ClO4−/Zr-MCM-41 Nanoparticles Prepared at Mild Conditions: A Novel Solid Acid Catalyst for the Synthesis of Polyhydroquinolines, J. Iran. Chem. Soc., 13(7): 1339-1347 (2016).
[36] Abdollahi-Alibeik M., Rezaeipoor-Anari A., Fe3O4@B-MCM-41: A New Magnetically Recoverable Nanostructured Catalyst for the Synthesis of Polyhydroquinolines, J. Magn. Magn. Mater., 398: 205-214 (2016).
[37] Wang L.M., Sheng J., Zhang L., Han J.W., Fan Z.Y., Tian H., Qian C.T., Facile Yb(OTf)3 Promoted One-Pot Synthesis of Polyhydroquinoline Derivatives Through Hantzsch Reaction, Tetrahedron, 61(6): 1539-1543 (2005).
[38] Sapkal S.B., Shelke K.F., Shingate B.B., Shingare M., Nickel Nanoparticle-Catalyzed Facile and Efficient One-Pot Synthesis of Polyhydroquinoline Derivatives via Hantzsch Condensation Under Solvent-Free Conditions, Tetrahedron Lett., 50(15): 1754-1756 (2009).
[39] Mekheimer R.A., Hameed A.A., Sadek K.U., Solar Thermochemical Reactions: Four-Component Synthesis of Polyhydroquinoline Derivatives Induced by Solar Thermal Energy, Green Chem., 10(5): 592-593 (2008).
[40] Romanelli G.P., Autino J.C., Recent Applications of Heteropolyacids and Related Compounds in Heterocycles Synthesis, Mini-Rev. Org. Chem., 6(4): 359-366 (2009).
[41] Shimizu K., Furukawa H., Kobayashi N., Itaya Y., Satsuma A., Effects of Brønsted and Lewis Acidities on Activity and Selectivity of Heteropolyacid-Based Catalysts for Hydrolysis of Cellobiose and Cellulose, Green Chem., 11(10): 1627-1632 (2009).
[42] Vafaee A., Davoodnia A., Pordel M., A Rapid, Efficient, and High-Yielding Synthesis of 4,4′-(Arylmethylene) bis(3-methyl-1H-pyrazol-5-ol) Derivatives Catalyzed by 12-Tungstophosphoric Acid (H3PW12O40), Res. Chem. Intermed., 41(11): 8343-8354 (2015).
[43] Kozhevnikov I.V., Catalysis by Heteropoly Acids and Multicomponent Polyoxometalates in Liquid-Phase Reactions, Chem. Rev., 98(1): 171-198 (1998).
[44] Zheng X., Zhang L., Li J., Luo S., Cheng J.P., Magnetic Nanoparticle Supported Polyoxometalates (POMs) via Non-Covalent Interaction: Reusable Acid Catalysts and Catalyst Supports for Chiral Amines, Chem. Commun., 47(45): 12325-12327 (2011).
[45] Hamadi H., Kooti M., Afshari M., Ghiasifar Z., Adibpour N., Magnetic Nanoparticle Supported Polyoxometalate: An Efficient and Reusable Catalyst for Solvent-Free Synthesis of α-Aminophosphonates, J. Mol. Catal. A: Chem., 373: 25-29 (2013).
[46] Zhang Z., Zhang F., Zhu Q., Zhao W., Ma B., Ding Y., Magnetically Separable Polyoxometalate Catalyst for the Oxidation of Dibenzothiophene With H2O2, J. Colloid Interface Sci.,360(1): 189-194 (2011).
[47] Cui X., Yao D., Li H., Yang J., Hu D., Nano-Magnetic Particles as Multifunctional Microreactor for Deep Desulfurization, J. Hazard. Mater., 205-206: 17-23 (2012).
[48] Davoodnia A., Roshani M., Saleh Nadim E., Bakavoli M., Tavakoli Hoseini N., Microwave-Assisted Synthesis of New Pyrimido[4′,5′:4,5]thiazolo[3,2-a] benzimidazol-4(3H)-one Derivatives in Solvent-Free Condition, Chin. Chem. Lett.,18(11): 1327-1330 (2007).
[49] Davoodnia A., Bakavoli M., Bashash M., Roshani M., Zhiani R., Synthesis of New 5-Arylpyrido[3′,2′:4,5]thieno[2,3-e] [1,2,3,4]tetrazolo [1,5-c]pyrimidine Derivatives, Turk. J. Chem., 31(6): 599-603 (2007).
[50] Ameli S., Davoodnia A., Pordel M., Behmadi H., Synthesis of New Imino Containing Tetrahydrochromeno[2,3-d]pyrimidines, J. Heterocycl. Chem., 54(2): 1437-1441 (2017).
[51] Davoodnia A., Heravi M.M., Rezaei-Daghigh R., Tavakoli-Hoseini T., A Modified and Green Procedure for The Synthesis of β-Amido Ketones Using a Brønsted-Acidic Ionic Liquid as Novel and Reusable Catalyst, Chin. J. Chem., 28(3): 429-433 (2010).
[52] Yassaghi G., Davoodnia A., Allameh S., Zare-Bidaki A., Tavakoli-Hoseini N., Preparation, Characterization and First Application of Aerosil Silica Supported Acidic Ionic Liquid as a Reusable Heterogeneous Catalyst for the Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones, Bull. Korean Chem. Soc., 33(8): 2724-2730 (2012).
[53] Tavakoli-Hoseini N., Davoodnia A., Carbon-Based Solid Acid as an Efficient and Reusable Catalyst for One-Pot Synthesis of Tetrasubstituted Imidazoles Under Solvent-Free Conditions, Chin. J. Chem., 29(1): 203-206 (2011).
[54] Davoodnia A., Zare-Bidaki A., Behmadi H., A Rapid and Green Method for Solvent-Free Synthesis Of 1,8-Dioxodecahydroacridines Using Tetrabutylammonium Hexatungstate as a Reusable Heterogeneous Catalyst, Chin. J. Catal., 33(11): 1797-1801 (2012).
[55] Davoodnia A., Nakhaei A., Tavakoli-Hoseini N., Catalytic Performance of a Keplerate-Type, Giant-Ball Nanoporous Isopolyoxomolybdate as A Highly Efficient Recyclable Catalyst for the Synthesis of Biscoumarins, Z. Naturforsch., 71b(3): 219-225 (2016).
[56] Lee B., Kang P., Lee K.H., Cho J., Nam W., Lee W.K., Hur N.H., Solid-State and Solvent-Free Synthesis of Azines, Pyrazoles, and Pyridazinones Using Solid Hydrazine, Tetrahedron Lett., 54(11): 1384-1388 (2013).
[57] Bazgir A., Hosseini G., Ghahremanzadeh R., Copper Ferrite Nanoparticles: An Efficient and Reusable Nanocatalyst for a Green One-Pot, Three-Component Synthesis of Spirooxindoles in Water, ACS Comb. Sci., 15(10): 530-534 (2013).
[58] Swami S., Agarwala A., Shrivastava R., Sulfonic Acid Functionalized Silica-Coated CuFe2O4 Core-Shell Nanoparticles: An Efficient and Magnetically Separable Heterogeneous Catalyst for the Synthesis of 2-Pyrazole-3-Amino-Imidazo-Fused Polyheterocycles, New J. Chem., 40(11): 9788-9794 (2016).
[59] Kotadia D.A., Soni S.S., Silica Gel Supported -SO3H Functionalised Benzimidazolium Based Ionic Liquid as a Mild and Effective Catalyst for Rapid Synthesis of 1-Amidoalkyl naphthols, J. Mol. Catal. A: Chem., 353-354: 44-49 (2012).
Iranian Journal of Chemistry and Chemical Engineering
Volume 38, Issue 5 - Serial Number 97
September and October 2019
Pages 65-77

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