Fe₃O₄@C@PrS-SO₃H: A Novel Efficient Magnetically Recoverable Heterogeneous Catalyst in the Ultrasound-Assisted Synthesis of Coumarin Derivatives

References

• M. J. Climent, A. Corma, and S. Iborra, “Heterogeneous Catalysts for the One-Pot Synthesis of Chemicals and Fine Chemicals,” Chemical Reviews 111, no. 2 (2011): 1072–133.
   PubMed Web of Science ®Google Scholar
• D. A. Petrone, J. Ye, and M. Lautens, “Modern Transition-Metal-Catalyzed Carbon-Halogen Bond Formation,” Chemical Reviews 116, no. 14 (2016): 8003–104.
   PubMed Web of Science ®Google Scholar
• E. Vessally, S. Soleimani-Amiri, A. Hosseinian, L. Edjlali, and M. Babazadeh, “Chemical Fixation of CO2 to 2-Aminobenzonitriles: A Straightforward Route to Quinazoline-2,4(1H,3H)-Diones with Green and Sustainable Chemistry Perspectives,” Journal of CO2 Utilization 21 (2017): 342–52.
   Web of Science ®Google Scholar
• S. Soleimani Amiri, “Green Production and Antioxidant Activity Study of New Pyrrolo[2,1-a]Isoquinolines,” Journal of Heterocyclic Chemistry 57, no. 11 (2020): 4057–69.
   Web of Science ®Google Scholar
• A. Mojaverian Kermani, V. Mahmoodi, M. Ghahramaninezhad, and A. Ahmadpour, “Highly Efficient and Green Catalyst of {Mo132} Nanoballs Supported on Ionic Liquid-Functionalized Magnetic Silica Nanoparticles for Oxidative Desulfurization of Dibenzothiophene,” Separation and Purification Technology 258 (2021): 117960.
   Web of Science ®Google Scholar
• M. Helmi, K. Tahvildari, A. Hemmati, P. Aberoomand Azar, and A. Safekordi, “Phosphomolybdic Acid/Graphene Oxide as Novel Green Catalyst Using for Biodiesel Production from Waste Cooking Oil via Electrolysis Method: Optimization Using with Response Surface Methodology (RSM),” Fuel 287 (2021): 119528.
   Web of Science ®Google Scholar
• M. Kazemi, “Based on MFe2O4 (M = Co, Cu, and Ni): Magnetically Recoverable Nanocatalysts in Synthesis of Heterocyclic Structural Scaffolds,” Synthetic Communications 50, no. 13 (2020): 1899–935.
   Web of Science ®Google Scholar
• A. Ghorbani-Choghamarani, M. Mohammadi, R. H. E. Hudson, and T. Tamoradi, “Boehmite@tryptophan-Pd Nanoparticles: A New Catalyst for C–C Bond Formation,” Applied Organometallic Chemistry 33, no. 8 (2019): e4977.
   Web of Science ®Google Scholar
• S. Ahmadi, A. Hosseinian, P. Delir Kheirollahi Nezhad, A. Monfared, and E. Vessally, “Nano-Ceria (CeO2): an Efficient Catalyst for the Multi-Component Synthesis of a Variety of Key Medicinal Heterocyclic Compounds,” Iranian Journal of Chemistry and Chemical Engineering (IJCCE) 38, no. 6 (2019): 1–19.
   Google Scholar
• 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.
   Web of Science ®Google Scholar
• S. Abdolmohammadi, and Z. Hossaini, “Fe3O4 MNPs as a Green Catalyst for Syntheses of Functionalized [1,3]-Oxazole and 1H-Pyrrolo-[1,3]-Oxazole Derivatives and Evaluation of Their Antioxidant Activity,” Molecular Diversity 23, no. 4 (2019): 885–96.
   PubMed Web of Science ®Google Scholar
• F. Chaghari-Farahani, S. Abdolmohammadi, and R. Kia-Kojoori, “A PANI-Fe3O4@ZnO Nanocomposite: A Magnetically Separable and Applicable Catalyst for the Synthesis of Chromeno-Pyrido[d]Pyrimidine Derivatives,” RSC Advances 10, no. 26 (2020): 15614–21.
   PubMed Web of Science ®Google Scholar
• F. Shafaei, S. E. Babaei, A. S. Shahvelayati, and F. Honarmand Janatabadi, “Biosynthesis of Fe3O4-Magnetic Nanoparticles Using Clover Leaf Aqueous Extract: Green Synthesis of 1,3-Benzoxazole Derivatives,” Journal of the Chinese Chemical Society 67, no. 5 (2020): 891–7.
   Web of Science ®Google Scholar
• Gabino Gonzalez-Carrillo, Jorge Gonzalez, Maria Jose Emparan-Legaspi, Gisela Jareth Lino-Lopez, Ismael A. Aguayo-Villarreal, Silvia G. Ceballos-Magaña, Francisco J. Martinez-Martinez, and Roberto Muñiz-Valencia, “Propylsulfonic Acid Grafted on Mesoporous Siliceous FDU-5 Material: A High TOF Catalyst for the Synthesis of Coumarins via Pechmann Condensation,” Microporous and Mesoporous Materials 307 (2020): 110458.
   Web of Science ®Google Scholar
• G. Özgül Artuç, B. Karapınar, M. Özdemir, and M. Bulut, “Synthesis, Characterization, and Determination of Photophysicochemical Properties of Peripheral and Nonperipheral Tetra-7-Oxy-3,4-Dimethylcoumarin Substituted Zinc, Indium Phthalocyanines,” Applied Organometallic Chemistry 35, no. 1 (2021): e6061.
   Web of Science ®Google Scholar
• F. Rajabi, A. Feiz, and R. Luque, “An Efficient Synthesis of Coumarin Derivatives Using a SBA-15 Supported Cobalt(II) Nanocatalyst,” Catalysis Letters 145, no. 8 (2015): 1621–5.
   Web of Science ®Google Scholar
• A. Mirosanloo, D. Zareyee, and M. A. Khalilzadeh, “Recyclable Cellulose Nanocrystal Supported Palladium Nanoparticles as an Efficient Heterogeneous Catalyst for the Solvent-Free Synthesis of Coumarin Derivatives via Von Pechmann Condensation,” Applied Organometallic Chemistry 32, no. 12 (2018): e4546.
   Web of Science ®Google Scholar
• E. Jafari, P. Farajzadeh, N. Akbari, and A. Karbakhshzadeh, “An Efficient and Facile Synthesis of the Coumarin and Ester Derivatives Using Sulfonated Polyionic Liquid as a Highly Active Heterogeneous Catalyst,” Chemical Review and Letters 2, no. 3 (2019): 123–9.
   Google Scholar
• M. Kiani, and B. Karami, “Nanosilica Molybdic Acid: synthesis, Characterization and Application as a Green and Reusable Catalyst for the Pechmann Condensation,” Journal of the Iranian Chemical Society 14, no. 3 (2017): 655–63.
   Web of Science ®Google Scholar
• O. Veselý, M. Shamzhy, M. Mazur, and P. Eliášová, “Zeolites in Pechmann Condensation: Impact of the Framework Topology and Type of Acid Sites,” Catalysis Today 345 (2020): 97–109.
   Web of Science ®Google Scholar
• F. K. Esfahani, D. Zareyee, and R. Yousefi, “Sulfonated Core-Shell Magnetic Nanoparticle (Fe3O4@SiO2@PrSO3H) as a Highly Active and Durable Protonic Acid Catalyst; Synthesis of Coumarin Derivatives through Pechmann Reaction,” Chemcatchem. 6, no. 12 (2014): 3333–7.
   Web of Science ®Google Scholar
• A. Mobaraki, S. Yasham, and B. Movassagh, “Environmentally Sustainable Magnetic Solid Sulfonic Acid: An Efficient and Reusable Catalyst for the Pechmann Reaction,” Synlett 26, no. 09 (2015): 1263–8.
   Google Scholar
• M. Samadizadeh, S. Nouri, and F. Kiani Moghadam, “Magnetic Nanoparticles Functionalized Ethane Sulfonic Acid (MNESA): as an Efficient Catalyst in the Synthesis of Coumarin Derivatives Using Pechmann Condensation under Mild Condition,” Research on Chemical Intermediates 42, no. 6 (2016): 6089–103.
   Web of Science ®Google Scholar
• Z. Abbasi, S. Rezayati, M. Bagheri, and R. Hajinasiri, “Preparation of a Novel, Efficient, and Recyclable Magnetic Catalyst, γ-Fe2O3@HAp-Ag Nanoparticles, and a Solvent- and Halogen-Free Protocol for the Synthesis of Coumarin Derivatives,” Chinese Chemical Letters 28, no. 1 (2017): 75–82.
   Web of Science ®Google Scholar
• Z. Samiei, S. Soleimani-Amiri, and Z. Azizi, “Fe3O4@C@OSO3H as an Efficient, Recyclable Magnetic Nanocatalyst in Pechmann Condensation: green Synthesis, Characterization, and Theoretical Study,” Molecular Diversity 25, no. 1 (2021): 67–86.
   PubMed Web of Science ®Google Scholar
• F. Zarei, S. Soleimani-Amiri, and Z. Azizi, “Heterogeneously Catalyzed Pechmann Condensation Employing the HFe(SO4)2.4H2O-Chitosan Nano-Composite: Ultrasound-Accelerated Green Synthesis of Coumarins,” Polycyclic Aromatic Compounds (2021): 1–18.doi: 10.1080/10406638.2021.1973520
   Web of Science ®Google Scholar
• Daniela R. Araujo, Yanka R. Lima, Angelita M. Barcellos, Márcio S. Silva, Raquel G. Jacob, Eder J. Lenardão, Luana Bagnoli, Claudio Santi, and Gelson Perin, “Ultrasound-Promoted Radical Synthesis of 5-Methylselanyl-4,5-Dihydroisoxazoles,” European Journal of Organic Chemistry 2020, no. 5 (2020): 586–92.
   Web of Science ®Google Scholar
• G. Mohammadi Ziarani, Z. Kheilkordi, and P. Gholamzadeh, “Ultrasound-Assisted Synthesis of Heterocyclic Compounds,” Molecular Diversity 24, no. 3 (2020): 771–820.
   PubMed Web of Science ®Google Scholar
• S. Abdolmohammadi, S. Shariati, and B. Mirza, “Ultrasound Promoted and Kit-6 Mesoporous Silica-Supported Fe3O4 Magnetic Nanoparticles Catalyzed Cyclocondensation Reaction of 4-Hydroxycoumarin, 3,4-Methylenedioxyphenol, and Aromatic Aldehydes,” Applied Organometallic Chemistry 35, no. 3 (2021): e6117.
   Web of Science ®Google Scholar
• A. S. Shahvelayati, M. Sabbaghan, and S. Banihashem, “Sonochemically Assisted Synthesis of N-Substituted Pyrroles Catalyzed by ZnO Nanoparticles under Solvent-Free Conditions,” Monatshefte Für Chemie - Chemical Monthly 148, no. 6 (2017): 1123–9.
   Google Scholar
• H. Ghavidel, B. Mirza, S. Soleimani-Amiri, and M. Manafi, “New Insight into Experimental and Theoretical Mechanistic Study on a Green Synthesis of Functionalized 4H-Chromenes Using Magnetic Nanoparticle Catalyst,” Journal of the Chinese Chemical Society 67, no. 10 (2020): 1856–76.
   Web of Science ®Google Scholar
• H. Ghavidel, B. Mirza, and S. Soleimani-Amiri, “A Novel, Efficient, and Recoverable Basic Fe3O4@C Nano-Catalyst for Green Synthesis of 4H-Chromenes in Water via One-Pot Three Component Reactions,” Polycyclic Aromatic Compounds 41, no. 3 (2021): 604–25.
   Web of Science ®Google Scholar
• S. F. Taheri Hatkehlouei, B. Mirza, and S. Soleimani-Amiri, “Solvent-Free One-Pot Synthesis of Diverse Dihydropyrimidinones/Tetrahydropyrimidinones Using Biginelli Reaction Catalyzed by Fe3O4@C@OSO3H,” Polycyclic Aromatic Compounds (2020): 1–17.doi: 10.1080/10406638.2020.1781203
   Web of Science ®Google Scholar
• P. Kamalzare, B. Mirza, and S. Soleimani-Amiri, “Chitosan Magnetic Nanocomposite: A Magnetically Reusable Nanocatalyst for Green Synthesis of Hantzsch 1,4-Dihydropyridines under Solvent-Free Conditions,” Journal of Nanostructure in Chemistry 11, no. 2 (2021): 229–43. +.
   Web of Science ®Google Scholar
• N. Nasehi, B. Mirza, and S. Soleimani-Amiri, “Fe3O4@C@prNHSO3H: A Novel Magnetically Recoverable Heterogeneous Catalyst in Green Synthesis of Diverse Triazoles,” Journal of the Chinese Chemical Society 68, no. 11 (2021): 2071–84.
   Web of Science ®Google Scholar
• S. Kangari, I. Yavari, and B. Maasoumi, “Synthesis and Heterogeneous Catalytic Activity of Covalently Immobilized Hexamine Cation as a Magnetically-Recoverable Nanocatalyst,” Journal of the Iranian Chemical Society 12, no. 10 (2015): 1771–9.
   Web of Science ®Google Scholar
• F. Shirini, M. A. Zolfigol, and J. Albadi, “Melamine Trisulfonic Acid as a New, Efficient and Reusable Catalyst for the Solvent Free Synthesis of Coumarins,” Journal of the Iranian Chemical Society 7, no. 4 (2010): 895–9.
   Web of Science ®Google Scholar
• R. S. Keri, K. M. Hosamani, and H. R. Seetharama Reddy, “A Solvent-Free Synthesis of Coumarins Using Phosphotungstic Acid as Catalyst,” Catalysis Letters 131, no. 1-2 (2009): 321–7.
   Web of Science ®Google Scholar
• S. S. Bahekar, and D. B. Shinde, “Samarium (III) Catalyzed One-Pot Construction of Coumarins,” Tetrahedron Letters 45, no. 43 (2004): 7999–8001.
   Web of Science ®Google Scholar
• J. D’Souza, and N. Nagaraju, “Clean and Efficient Synthesis of Coumarins over Modified Metal Oxides via Pechmann Reaction,” Indian Journal of Chemical Technology 15 (2008): 244–251.
   Google Scholar
• Christophe Guillon, Yi-Hua Jan, Diane E. Heck, Thomas M. Mariano, Robert D. Rapp, Michele Jetter, Keith Kardos, Marilyn Whittemore, Eric Akyea, Ivan Jabin, et al, “Phototoxicity of 7-Oxycoumarins with Keratinocytes in Culture,” Bioorganic Chemistry 89 (2019): 103014.
   PubMed Web of Science ®Google Scholar
• Baoxin Zhang, Chunpo Ge, Juan Yao, Yaping Liu, Huichen Xie, and Jianguo Fang, “Selective Selenol Fluorescent Probes: design, Synthesis, Structural Determinants, and Biological Applications,” Journal of the American Chemical Society 137, no. 2 (2015): 757–69.
   PubMed Web of Science ®Google Scholar
• K. Jung, Y.-J. Park, and J.-S. Ryu, “Scandium(III) Triflate–Catalyzed Coumarin Synthesis,” Synthetic Communications 38, no. 24 (2008): 4395–406.
   Web of Science ®Google Scholar
• E. R. Bissell, D. K. Larson, and M. C. Croudace, “Some 7-Substituted-4-(Trifluoromethyl)Coumarins,” Journal of Chemical & Engineering Data 26, no. 3 (1981): 348–50.
   Web of Science ®Google Scholar