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Research Articles

Fe3O4@nSiO2@mSiO2/DBU: A Novel and Effective Basic Magnetic Nanocatalyst in the Multicomponent One Pot Synthesis of Polyhydroacridines and Polyhydroquinolines

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Pages 1728-1746 | Received 13 May 2020, Accepted 29 Jul 2020, Published online: 17 Aug 2020

References

  • R. Karimi-Chayjani, N. Daneshvar, M. S. N. Langarudi, F. Shirini, and H. Tajik, “Silica-Coated Magnetic Nanoparticles Containing Bis Dicationic Bridge for the Synthesis of 1,2,4-Triazolo Pyrimidine/Quinazolinone Derivatives,” Journal of Molecular Structure 1199, (2020): 126891.
  • M. Vahidian, D. Elhamifar, and M. Shaker, “Core–Shell Structured Magnetic Mesoporous Silica-Titania: A Novel, Powerful and Recoverable Nanocatalyst,” Polyhedron 178, (2020): 114326.
  • O. V. Salata, “Applications of Nanoparticles in Biology and Medicine,” Journal of Nanobiotechnology 2, no. 1 (2004): 3.
  • F. Habeche, M. Hachemaoui, A. Mokhtar K. Chikh, F. Benali, A. Mekki, F. Zaoui, Z. Cherifi, and B. Boukoussa, “Recent Advances on the Preparation and Catalytic Applications of Metal Complexes Supported-Mesoporous Silica MCM-411,” Journal of Inorganic and Organometallic Polymers and Materials, (2020). doi: https://doi.org/10.1007/s10904-020-01689-1
  • A. Kohzadian and A. Zare, “Efficient and Highly Selective Production of 10,11-Dihydrochromeno[4,3-b]Chromene-6,8(7H,9H)-Diones Using a Mesoporous Silica-Based Nanocatalyst,” Research on Chemical Intermediates 45, no. 11 (2019): 5473–85.
  • M. Kazemi and M. Ghobadi, “Magnetically Recoverable Nano-Catalysts in Sulfoxidation Reactions,” Nanotechnology Reviews 6, no. 6 (2017): 549–71.
  • V. Somjit, M. Wong Chi Man, A. Ouali, P. Sangtrirutnugul, and V. Ervithayasuporn, “Heterogeneous Pd/POSS Nanocatalysts for C-C Cross-Coupling Reactions,” Chemistry Select 3, no. 2 (2018): 753–9.
  • R. K. Sharma, R. Gaur, M. Yadav, A. Goswami, R. Zbořil, and M. B. Gawande, “An efficient copper-based magnetic nanocatalyst for the fixation of carbon dioxide at atmospheric pressure,” Scientific Reports 8, (2018): 1–12.
  • S. B. Singh and P. K. Tandon, “Catalysis: a brief review on nano-catalyst,” Journal of Energy and Chemistry Engineering 2, (2014): 106–15.
  • A. Ghorbani-Choghamarani, M. Mohammadi, Z. Taherinia, and J. Iran, “ZrO)2Fe2O5 as an Efficient and Recoverable Nanocatalyst in C–C Bond Formation,” Journal of the Iranian Chemical Society 16, no. 2 (2019): 411–21.
  • A. Ghorbani‐Choghamarani, M. Mohammadi, R. Hudson, and T. Tamoradi, “Boehmite@ tryptophan‐Pd nanoparticles: A new catalyst for C–C bond formation,” Applied Organometallic Chemistry 33, (2019): e4977.
  • A. Ghorbani‐Choghamarani and M. Mohammadi, “l-Methionine–Pd Complex Supported on Hercynite as a Highly Efficient and Reusable Nanocatalyst for C–C Cross-Coupling Reactions,” New Journal of Chemistry 44, no. 7 (2020): 2919–29.
  • T. Tamoradi, S. M. Mousavi, and M. Mohammadi, “C − C and C − S Coupling Catalyzed by Supported Cu(II) on Nano CoFe 2 O 4,” Chemistry Select 5, no. 17 (2020): 5077–81.
  • L. Chen, A. Noory Fajer, Zh Yessimbekov, M. Kazemi, and M. Mohammadi, “Diaryl Sulfides Synthesis: copper Catalysts in C–S Bond Formation,” Journal of Sulfur Chemistry 40, no. 4 (2019): 451–68.
  • A. Ghorbani‐Choghamarani, H. Aghavandi, and M. Mohammadi, “Boehmite@ SiO2@ Tris (hydroxymethyl) aminomethane‐Cu (I): a novel, highly efficient and reusable nanocatalyst for the C‐C bond formation and the synthesis of 5‐substituted 1H‐tetrazoles in green media,” Applied Organometallic Chemistry, (2020): e5804.
  • A. Maleki, R. Taheri-Ledari, R. Ghalavand, and R. Firouzi-Haji, “Palladium-Decorated o-Phenylenediamine-Functionalized Fe3O4/SiO2 Magnetic Nanoparticles: A Promising Solid-State Catalytic System Used for Suzuki–Miyaura Coupling Reactions,” Journal of Physical Chemistry Solids 136, (2020): 109200.
  • A. Sheoran, J. Kaur, P. Kaur, V. Kumar, K. B. Tikoo, J. Agarwal, S. Bansal, and S. Singhal, “Graphene Based Magnetic Nanohybrids as Promising Catalysts for the Green Synthesis of β-Amino Alcohol Derivatives,” Journal of Molecular Structure 1204, (2020): 127522.
  • A. Ahmadi, T. Sedaghat, R. Azadi, and H. Motamedi, “Magnetic Mesoporous Silica Nanocomposite Functionalized with Palladium Schiff Base Complex: Synthesis, Characterization, Catalytic Efficacy in the Suzuki–Miyaura Reaction and α-Amylase Immobilization,” Catalysis Letters 150, no. 1 (2020): 112–26.
  • H. Filian, A. Ghorbani-Choghamarani, E. Tahanpesar, and J. Iran, “Ni-Guanidine@MCM-41 NPs: A New Catalyst for the Synthesis of 4,4′-(Arylmethylene)-Bis-(3-Methyl-1-Phenyl-1H-Pyrazol-5-Ols) and Symmetric di-Aryl Sulfides,” Journal of the Iranian Chemical Society 16, no. 12 (2019): 2673–81.
  • A. Zare, A. Kohzadian, Z. Abshirini, S. Sajad Sajadikhah, J. Phipps, M. Benamara, and M. Hassan Beyzavi, “Nano-2-(Dimethylamino)-N-(Silica-n-Propyl)-N, N-Dimethylethanaminium Chloride as a Novel Basic Catalyst for the Efficient Synthesis of Pyrido[2,3-d :6,5-d ′]Dipyrimidines,” New Journal of Chemistry 43, no. 5 (2019): 2247–57.
  • A. R. Moosavi-Zare, M. A. Zolfigol, V. Khakyzadeh, C. Böttcher, M. H. Beyzavi, A. Zare, A. Hasaninejad, and R. Luque, “Facile Preparation of a Nanostructured Functionalized Catalytically Active Organosalt,” Journal of Materials Chemistry 2, no. 3 (2014): 770–7.
  • A. Kohzadian, H. Filian, Z. Kordrostami, A. Zare, and A. Ghorbani-Choghamarani, “A Simple, Rapid and Effective Protocol for Synthesis of Bis(Pyrazolyl)Methanes Using Nickel–Guanidine Complex Immobilized on MCM-41,” Research on Chemical Intermediates 46, no. 3 (2020): 1941–53.
  • M. Nikoorazm, M. Khanmoradi, and M. Mohammadi, “Guanine‐La complex supported onto SBA‐15: A novel efficient heterogeneous mesoporous nanocatalyst for one‐pot, multi‐component Tandem Knoevenagel condensation–Michael addition–cyclization Reactions,” Applied Organometallic Chemistry 34, (2020): e5504.
  • H. Filian, A. Kohzadian, M. Mohammadi, A. Ghorbani, Choghamarani, and A. Karami, “Pd (0)‐guanidine@ MCM‐41: a very effective catalyst for rapid production of bis (pyrazolyl) methanes 25- A Novel Magnetic Immobilized Para-Aminobenzoic Acid-Cu(II) Complex: A Green, Efficient and Reusable Catalyst for Aldol Condensation Reactions in Green Media,” Applied Organometallic Chemistry 34, (2020): e5579.
  • Z. Esam, M. Akhavan, A. Bekhradnia, M. Mohammadi, and S. Tourani, Catalysis Letters (2020)
  • M. Nikoorazm, M. Mohammadi, and M. Khanmoradi, “Zirconium@guanine@MCM‐41 nanoparticles: An efficient heterogeneous mesoporous nanocatalyst for one‐pot, multi‐component tandem Knoevenagel condensation–Michael addition–cyclization Reactions,” Applied Organometallic Chemistry 34, (2020): e5704.
  • M. Haji, “ Multicomponent reactions: A simple and efficient route to heterocyclic phosphonates,” Beilstein Journal of Organic Chemistry 12, (2016): 1269–301.
  • A. Kohzadian and A. Zare, “Effective and Rapid Synthesis of Pyrido[2,3-d:6,5-d′]Dipyrimidines Catalyzed by a Mesoporous Recoverable Silica-Based Nanomaterial,” Silicon 12, no. 6 (2020): 1407–15.
  • Springer Science & Business Media R. P. Gore, and A. P. Rajput. “A review on recent progress in multicomponent reactions of pyrimidine synthesis,” Drug Invention Today 5, no. 2, (2013): 148-152.
  • K. N. Tiwari, M. R. Uttam, P. Kumari, P. Vatsa, and S. Prabhakaran, “Efficient Synthesis of Acridinediones in Aqueous Media,” Synthetic Communications 47, no. 10 (2017): 1013–9.
  • R. Kardooni, A. R. Kiasat, and H. Motamedi, “Designing of a Novel Dual-Function Silica-Iron Oxide Hybrid Based Nanocomposite, Fe 3 O 4 @SiO 2 PEG/NH 2, and Its Application as an Eco-Catalyst for the Solvent-Free Synthesis of Polyhydroacridines and Polyhydroquinolines,” Journal of the Taiwan Institute of Chemical Engineers 81, (2017): 373–82.
  • M. A. Ashraf, Z. Liu, W.-X. Peng, and C. Gao, “New Copper Complex on Fe3O4 Nanoparticles as a Highly Efficient Reusable Nanocatalyst for Synthesis of Polyhydroquinolines in Water,” Catalysis Letters 150, no. 3 (2020): 683–701.
  • D. K. Jamale, S. S. Undare, N. J. Valekar, A. P. Sarkate, G. B. Kolekar, and P. V. Anbhule, “Glycerol Mediated Synthesis, Biological Evaluation, and Molecular Docking Study of 4‐(1H‐pyrazol‐4‐yl)‐polyhydroquinolines as Potent Antitubercular Agents,” Journal of Heterocyclic Chemistry 56, (2019): 608–18.
  • S. J. Saghanezhad, M. H. Sayahi, I. Imanifar, M. Mombeni, and S. D. Hamood, “Caffeine-H3PO4: A Novel Acidic Catalyst for Various One-Pot Multicomponent Reactions,” Research on Chemical Intermediates 43, no. 11 (2017): 6521–36.
  • H. Ahankar, A. Ramazani, and S. W. Joo, “Magnetic Nickel Ferrite Nanoparticles as an Efficient Catalyst for the Preparation of Polyhydroquinoline Derivatives under Microwave Irradiation in Solvent-Free Conditions,” Research on Chemical Intermediates 42, no. 3 (2016): 2487–500.
  • S. Jadhvar, H. Kasraliker, S. Goswami, A. Chakrawar, and S. Bhusare, “One-Pot Synthesis and Evaluation of Anticancer Activity of Polyhydroquinoline Derivatives Catalyzed by [Msim]Cl,” Research on Chemical Intermediates 43, no. 12 (2017): 7211–21.
  • G.-H. Gong, M. Bian, C.-Y. Liu, and B. Zhang, “Heterocyclic Pyran and Polyhydroquinoline Derivatives to Inhibit Human Breast Cancer Cells,” Main Group Chemistry 18, no. 1 (2019): 15–22.
  • S. Rahmani and A. Amoozadeh, “Nano Titanium Dioxide: Efficient and Reusable Heterogeneous Nano Catalyst for Synthesis of 1, 8-Dioxo-Decahydroacridines,” Journal of Nanostructure 1, (2014): 91–8.
  • A. Ghorbani-Choghamarani, M. Mohammadi, T. Tamoradi, and M. Ghadermazi, “Covalent Immobilization of Co Complex on the Surface of SBA-15: Green, Novel and Efficient Catalyst for the Oxidation of Sulfides and Synthesis of Polyhydroquinoline Derivatives in Green Condition,” Polyhedron 158, (2019): 25–35.
  • G. Brahmachari, S. Begam, and K. Nurjamal, “Bismuth Nitrate Catalyzed One-Pot Multicomponent Synthesis of a Novel Series of Diversely Substituted 1,8-Dioxodecahydroacridines at Room Temperature #,” Chemistry Select 2, no. 11 (2017): 3311–6.
  • K. Mohammadi, F. Shirini, and A. Yahyazadeh, “1, 3-Disulfonic Acid Imidazolium Hydrogen Sulphate as an Efficient and Reusable Ionic Liquid for the Multicomponent Synthesis of Polyhydroquinoline Derivatives under Solvent-Free Conditions,” Research on Chemical Intermediates 42, no. 3 (2016): 2047–54.
  • F. Moheiseni, A. R. Kiasat, and R. Badri, Polycyclic Aromatic Compounds (2019),
  • R. Surasani, D. Kalita, A. D. Rao, K. Yarbagi, and K. B. Chandrasekhar, “FeF3 as a Novel Catalyst for the Synthesis of Polyhydroquinoline Derivatives via Unsymmetrical Hantzsch Reaction,” Journal of Fluorine Chemistry 135, (2012): 91–6.
  • B. Das, B. Ravikanth, R. Ramu, and B. V. Rao, “An Efficient One-Pot Synthesis of Polyhydroquinolines at Room Temperature Using HY-Zeolite,” Chemical & Pharmaceutical Bulletin 54, no. 7 (2006): 1044–5.
  • M. Yarie, M. A. Zolfigol, Y. Bayat, A. Asgari, D. A. Alonso, and A. Khoshnood, “Novel Magnetic Nanoparticles with Ionic Liquid Tags as a Reusable Catalyst in the Synthesis of Polyhydroquinolines,” RSC Advances 6, no. 86 (2016): 82842–53.82842-82853
  • M. Kazemi, and M. Mohammadi, Applied Organometallic Chemistry 34, (2020): e5400.
  • T. Tamoradi, S. M. Mousavi, and M. Mohammadi, “Synthesis of a New Ni Complex Supported on CoFe 2 O 4 and Its Application as an Efficient and Green Catalyst for the Synthesis of Bis(Pyrazolyl)Methane and Polyhydroquinoline Derivatives,” New Journal of Chemistry 44, no. 20 (2020): 8289–302.
  • A. Ghorbani-Choghamarani, M. Mohammadi, L. Shiri, and Z. Taherinia, “Synthesis and Characterization of Spinel FeAl2O4 (Hercynite) Magnetic Nanoparticles and Their Application in Multicomponent Reactions,” Research on Chemical Intermediates 45, no. 11 (2019): 5705–23.
  • M. Hong, C. Cai, and W.-B. Yi, “Hafnium (IV) Bis(Perfluorooctanesulfonyl)Imide Complex Catalyzed Synthesis of Polyhydroquinoline Derivatives via Unsymmetrical Hantzsch Reaction in Fluorous Medium,” Journal of Fluorine Chemistry 131, no. 1 (2010): 111–4.
  • M. Jafari Nasab, and A. R. Kiasat, “Multifunctional Fe 3 O 4 @nSiO 2 @mSiO 2 /Pr-Imi-NH 2 ·Ag Core–Shell Microspheres as Highly Efficient Catalysts in the Aqueous Reduction of Nitroarenes: improved Catalytic Activity and Facile Catalyst Recovery,” RSC Advances 6, no. 48 (2016): 41871–7.
  • M. Ma, Y. Yang, D. Liao, P. Lyu, J. Zhang, J. Liang, and L. Zhang, “Synthesis, Characterization and Catalytic Performance of Core-Shell Structure Magnetic Fe 3 O 4 /P(GMA-EGDMA)-NH 2 /HPG-COOH-Pd Catalyst Core-Shell Magnetic Fe3O4/P(GMA-EGDMA)-NH2/HPG-COOH-Pd Catalyst,” Applied Organometallic Chemistry 33, no. 2 (2019): e4708.
  • A. Zare, M. Sadeghi-Takallo, M. Karami, and A. Kohzadian, “Synthesis, Characterization and Application of nano-N,N,N′,N′-tetramethyl-N-(Silica-n-Propyl)-N′-Sulfo-Ethane-1,2-Diaminium Chloride as a Highly Efficient Catalyst for the Preparation of N,N′-Alkylidene Bisamides,” Research on Chemical Intermediates 45, no. 5 (2019): 2999–3018.
  • K. Gerwert, and F. Siebert, “Evidence for Light-Induced 13-Cis, 14-s-Cis Isomerization in Bacteriorhodopsin Obtained by FTIR Difference Spectroscopy Using Isotopically Labelled Retinals,” The EMBO Journal 5, no. 4 (1986): 805–11.
  • D.L. Pavia, G.M. Lampman, G.S. Kriz, J.A. Vyvyan, Introduction to Spectroscopy, 5th ed. (Belmont, Cengage Learning, 2014)
  • M. Sarkheil, and M. Lashanizadegan, “New Magnetic Supported Hydrazone Schiff Base Dioxomolybdenum (VI) Complex: An Efficient Nanocatalyst for Epoxidation of Cyclooctene and Norbornene,” Applied Organometallic Chemistry 32, no. 9 (2018): e4459.
  • A. Biabani-Ravandi, and M. Rezaei, “Low Temperature CO Oxidation over Fe–Co Mixed Oxide Nanocatalysts,” Chemical Engineering Journal and the Biochemical Engineering Journal 184, (2012): 141–6.
  • M. Nikoorazm, A. Ghorbani, ‐Choghamarani, and M. Khanmoradi, “Application of Pd-2A3HP-MCM-41 to the Suzuki, Heck and Stille Coupling Reactions and Synthesis of 5-Substituted 1 H-Tetrazoles,” Applied Organometallic Chemistry 30, no. 8 (2016): 705–12.
  • M. Nikoorazm, A. Ghorbani-Choghamarani, N. Noori, and B. Tahmasbi, “Palladium 2-mercapto-N-Propylacetamide Complex Anchored onto MCM-41 as Efficient and Reusable Nanocatalyst for Suzuki, Stille and Heck Reactions and Amination of Aryl Halides,” Applied Organometallic Chemistry 30, no. 10 (2016): 843–51.
  • H. Filian, A. Ghorbani-Choghamarani, and E. Tahanpesar, “Pd(0)-Guanidine@MCM-41 as Efficient and Reusable Heterogeneous Catalyst for C–C Coupling Reactions,” Journal of Porous Materials 26, no. 4 (2019): 1091–101.

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