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Research Articles

2-Aminoisoindoline-1,3-Dione-Functionalized Fe3O4/Chloro-Silane Core-Shell Nanoparticles as Reusable Catalyst: An Efficient Heterogeneous Magnetic Nanoparticles for Synthesis of 4H-Pyran Derivatives through Multicomponent Reaction

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Pages 4561-4577 | Received 15 Jan 2021, Accepted 26 Feb 2021, Published online: 22 Mar 2021

References

  • R. V A. Orru and M. Greef, “Recent Advances in Solution Phase Multicomponent Methodology for the Synthesis of Heterocyclic Compounds,”Synthesis 10, no. 10 (2003): 1471–99.
  • A. Domling, “Recent Developments in Isocyanide Based Multicomponent Reactions in Applied Chemistry,”Chemical Reviews 106, no. 18 (2006): 17–89.
  • N. S. Babu, N. Pasha, K. T. V. Rao, P. S. S. Prasad, and N. A. Lingaiah, “A Heterogeneous Strong Basic Mg/La Mixed Oxide Catalyst for Efficient Synthesis of Polyfunctionalized Pyrans,”Tetrahedron Letters 49, no. 17 (2008): 2730–3.
  • J. F. Zhou, “One-Step Synthesis of Pyridine and 4H-Pyran Derivatives from Bisarylidenecyclohexanone and Malononitrile under Microwave Irradiation,”Synthetic Communications 33, no. 1 (2003): 99–103.
  • X. S. Wang, D. Q. Shi, Y. Du, Y. Zhou, and S. J. Tu, “Synthesis of 2-Aminopyran Derivatives and 3-Arylpropionitrile Derivatives Catalyzed by KF/Al2O3,”Synthetic Communications 34, no. 8 (2004): 1425–32.
  • T. S. Jin, L. B. Liu, Y. Zhao, and T. S. Li, “Clean, One-Pot Synthesis of 4H-Pyran Derivatives Catalyzed by Hexadecyltrimethyl Ammonium Bromide in Aqueous Media,”Synthetic Communications 35, no. 14 (2005): 1859–63.
  • M. Amirnejad, M. R. Naimi-Jamal, H. Tourani, and H. Ghafuri, “A Facile Solvent-Free One-Pot Three-Component Method for the Synthesis of 2-Amino-4H-Pyrans and Tetrahydro-4H-Chromenes at Ambient Temperature,”Monatshefte Für Chemie - Chemical Monthly 144, no. 8 (2013): 1219–25.
  • S. Nemouchi, R. Boulcina, B. Carboni, and A. Debache, “Phenylboronic Acid as an Efficient and Convenient Catalyst for a Three-Component Synthesis of Tetrahydrobenzo[b]Pyrans,”Comptes Rendus Chimie 15, no. 5 (2012): 394–7.
  • J. T. Li, W. Z. Xu, L. C. Yang, and T. S. Li, “One‐Pot Synthesis of 2‐Amino‐4‐Aryl‐3‐Carbalkoxy‐7,7‐Dimethyl‐5,6,7,8‐Tetrahydrobenzo[b]Pyran Derivatives Catalyzed by KF/Basic Al2O3 under Ultrasound Irradiation,”Synthetic Communications 34, no. 24 (2004): 4565–71. ”,
  • S. Rathod, B. Arbad, and M. Lande, “Preparation, Characterization, and Catalytic Application of a Nanosized Ce1MgxZr1-xO2 Solid Heterogeneous Catalyst for the Synthesis of Tetrahydrobenzo[b]Pyran Derivatives,”Chinese Journal of Catalysis 31, no. 6 (2010): 631–6.
  • Y. Li, B. Du, X. Wang, D. Shi, and S. Tu, “Synthesis of 2‐Amino‐4‐Aryl‐7,7‐Dimethyl‐5‐Oxo‐4H‐5,6,7,8‐Tetrahydrobenzo[b]Pyran Derivatives in Ionic Liquid Medium,”Journal of Heterocyclic Chemistry 43, no. 3 (2006): 685–8.
  • I. Devi and P. J. Bhuyan, “Sodium Bromide Catalysed One-Pot Synthesis of Tetrahydrobenzo[b]Pyrans via a Three-Component Cyclocondensation under Microwave Irradiation and Solvent Free Conditions,”Tetrahedron Letters 45, no. 47 (2004): 8625–7.
  • T. S. Jin, A. Q. Wang, X. Wang, J. S. Zhang, and T. S. Li, “A Clean One-Pot Synthesis of Tetrahydrobenzo[b]Pyran Derivatives Catalyzed by Hexadecyltrimethyl Ammonium Bromide in Aqueous Media,”Synlett 5, no. 5 (2004): 0871–7.
  • D. Tahmassebi, J. A. Bryson, and S. T. Binz, “1,4-Diazabicyclo[2.2.2]Octane as an Efficient Catalyst for a Clean, One-Pot Synthesis of Tetrahydrobenzo[b]Pyran Derivatives via Multicomponent Reaction in Aqueous Media,”Synthetic Communications 41, no. 18 (2011): 2701–11.
  • J. Zheng and Y. Li, “Basic Ionic Liquid-Catalyzed Multicomponent Synthesis of Tetrahydrobenzo[b]Pyrans and Pyrano[c]Chromenes,”Mendeleev Communications 21, no. 5 (2011): 280–1.
  • M. Moghaddas and A. Davoodnia, “Atom-Economy Click Synthesis of Tetrahydrobenzo[b]Pyrans Using Carbon-Based Solid Acid as a Novel, Highly Efficient and Reusable Heterogeneous Catalyst,”Research on Chemical Intermediates 41, no. 7 (2015): 4373–86.
  • S. Khaksar, A. Rouhollahpour, and S. Mohammadzadeh Talesh, “A Facile and Efficient Synthesis of 2-Amino-3-Cyano-4H-Chromenes and Tetrahydrobenzo[b]Pyrans Using 2,2,2-Trifluoroethanol as a Metal-Free and Reusable Medium,” Journal of Fluorine Chemistry 141, (2012): 11–5.
  • R. Hekmatshoar, S. Majedi, and K. Bakhtiari, “Sodium Selenate Catalyzed Simple and Efficient Synthesis of Tetrahydro Benzo [b] Pyran Derivatives,”Catalysis Communications 9, no. 2 (2008): 307–10.
  • B. Abrahamsen, N. Schneider, M. N. Erichsen, T. H. V. Huynh, C. Fahlke, L. Bunch, and A. A. Jensen, “Allosteric Modulation of an Excitatory Amino Acid Transporter: The Subtype-Selective Inhibitor UCPH-101 Exerts Sustained Inhibition of EAAT1 through an Intramonomeric Site in the Trimerization Domain,”The Journal of Neuroscience : The Official Journal of the Society for Neuroscience 33, no. 3 (2013): 1068–87.
  • A. Rostami, B. Atashkar, and H. Gholami, “Novel Magnetic Nanoparticles Fe3O4-Immobilized Domino Knoevenagel Condensation, Michael Addition, and Cyclization Catalyst,” Catalysis Communications 37, (2013): 69–74.
  • A. Rostami and B. Atashkar, “Synthesis, Characterization and Catalytic Property of Chiral oxo-Vanadium (+)-Pseudoephedrine Complex Supported on Magnetic Nanoparticles Fe3O4 in the Cyanosilylation of Carbonyl Compounds,” Catalysis Communications 58, (2015): 80–4.
  • B. Atashkar, A. Rostami, and B. Tahmasbi, “Magnetic Nanoparticle-Supported Guanidine as a Highly Recyclable and Efficient Nanocatalyst for the Cyanosilylation of Carbonyl Compounds,”Catalysis Science & Technology 3, no. 8 (2013): 2140–6.
  • C. Yuan, Y. Zhang, and J. Chen, “Molybdenum Oxide Supported on Hydroxyapatite- Encapsulated _-Fe2O3: A Novel Magnetically Recyclable Catalyst for Olefin,”Chinese Journal of Catalysis 32, no. 6–8 (2011): 1166–72.
  • R. Y. Hong, J. H. Li, S. Z. Zhang, H. Z. Li, Y. Zheng, J. M. Ding, and D. G. Wei, “Preparation and Characterization of Silica-Coated Fe3O4 Nanoparticles Used as Precursor of Ferrofluids,”Applied Surface Science 255, no. 6 (2009): 3485–92.
  • R. K. Sharma, Y. Monga, and A. Puri, “Zirconium (IV)-Modified Silica@Magnetic Nanocomposites: Fabrication, Characterization and Application as Efficient, Selective and Reusable Nanocatalysts for Friedel–Crafts, Knoevenagel and Pechmann Condensation Reactions,” Catalysis Communications 35, (2013): 110–4.
  • H. Yang, S. Li, W. Wang, F. Zhang, X. Zhong, Z. Dong, and J. Ma, “Core–Shell Silica Magnetic Microspheres Supported Proline as a Recyclable Organocatalyst for the Asymmetric Aldol Reaction,” Journal of Molecular Catalysis A: Chemical 363–364, (2012): 404–10.
  • F. Shahbazi and K. Amani, “Synthesis, Characterization and Heterogeneous Catalytic Activity of Diamine-Modified Silica-Coated Magnetite-Polyoxometalate Nanoparticles as a Novel Magnetically-Recoverable Nanocatalyst,” Catalysis Communications 55, (2014): 57–64.
  • A. Fihri, C. Len, R. S. Varma, and A. Solhy, “Hydroxyapatite: A Review of Syntheses, Structure and Applications in Heterogeneous Catalysis,”Coordination Chemistry Reviews 347, (2017): 48–76.
  • S. Pan, P. Li, G. Xu, J. Guo, L. Ke, C. Xie, C. Xie, Z. Zhang, and Y. Hui, “MCM-41@ Schiff base-Co (OAc)2 as an Efficient Catalyst for the Synthesis of Pyran Derivatives,”Research on Chemical Intermediates 46, no. 2 (2020): 1353–71.
  • B. Eshtehardian, M. Rouhani, and Z. Mirjafary, “Green Protocol for Synthesis of MgFe2O4 Nanoparticles and Study of Their Activity as an Efficient Catalyst for the Synthesis of Chromene and Pyran Derivatives under Ultrasound Irradiation,”Journal of the Iranian Chemical Society 17, no. 2 (2020): 469–81.
  • N. Azizi, S. Dezfooli, M. Khajeh, and M. M. Hashemi, “Efficient Deep Eutectic Solvents Catalyzed Synthesis of Pyran and Benzopyran Derivatives,” Journal of Molecular Liquids 186, (2013): 76–80.
  • M. K. Chaudhuri, S. Hussain, M. L. Kantam, and B. Neelima, “Boric Acid: A Novel and Safe Catalyst for aza-Michael Reactions in Water,”Tetrahedron Letters 46, no. 48 (2005): 8329–31.
  • S. K. Dangolani, F. Panahi, M. Nourisefat, and A. Khalafi-Nezhad, “4-Dialkylaminopyridine Modified Magnetic Nanoparticles: As an Efficient Nano-Organocatalyst for One-Pot Synthesis of 2-Amino-4H-Chromene-3-Carbonitrile Derivatives in Water,”RSC Advances 6, no. 95 (2016): 92316–24.
  • M. Hajjami, F. Gholamian, R. H. Hudson, and A. M. Sanati, “FSM-16/AEPC-SO3H: Synthesis, Characterization and Its Application for the Catalytic Preparation of 1,8-Dioxo-Octahydroxanthene and Tetrahydrobenzo[b]Pyran Derivatives,”Catalysis Letters 149, no. 1 (2019): 228–47.
  • J. M. Khurana and A. Chaudhary, “Efficient and Green Synthesis of 4H-Pyrans and 4H-Pyrano[2,3-c] Pyrazoles Catalyzed by Task-Specific Ionic Liquid [Bmim]OH under Solvent-Free Conditions,”Green Chemistry Letters and Reviews 5, no. 4 (2012): 633–8.
  • S. Banerjee, A. Horn, H. Khatri, and G. Sereda, “A Green One-Pot Multicomponent Synthesis of 4H-Pyrans and Polysubstituted Aniline Derivatives of Biological, Pharmacological, and Optical Applications Using Silica Nanoparticles as Reusable Catalyst,”Tetrahedron Letters 52, no. 16 (2011): 1878–81.
  • Y. Peng and G. Song, “Amino-Functionalized Ionic Liquid as Catalytically Active Solvent for Microwave-Assisted Synthesis of 4H-Pyrans,” Catalysis Communications 8, no. 2 (2007): 111–214.
  • E. Pourian, S. Javanshir, Z. Dolatkhah, S. Molaei, and A. Maleki, “Ultrasonic-Assisted Preparation, Characterization, and Use of Novel Biocompatible Core/Shell Fe3O4@GA@Isinglass in the Synthesis of 1,4-Dihydropyridine and 4H-Pyran Derivatives,”ACS Omega. 3, no. 5 (2018): 5012–20. − 
  • M. A. Bodaghifard, A. Mobinikhaledi, and S. Asadbegi, “Bis(4-Pyridylamino)Triazine-Stabilized Magnetite Nanoparticles: preparation, Characterization and Application as a Retrievable Catalyst for the Green Synthesis of 4H-Pyran, 4H-Thiopyran and 1,4-Dihydropyridine Derivatives,” Applied Organometallic Chemistry 31, no. 2 (2017) : e3557.
  • M. Kamalzare, M. Bayat, and A. Maleki, “Green and Efficient Three-Component Synthesis of 4H-Pyran Catalysed by CuFe2O4@Starch as a Magnetically Recyclable Bionanocatalyst,” Royal Society Open Science 7, no. 7 (2020): 200385–13. 200385,
  • M. G. Dekamin, M. Eslami, and A. Maleki, “Potassium phthalimide-N-Oxyl: A Novel, Efficient, and Simple Organocatalyst for the One-Pot Three-Component Synthesis of Various 2-Amino-4H-Chromene Derivatives in Water,”Tetrahedron 69, no. 3 (2013): 1074–85.
  • M. S. Esmaeili, M. R. Khodabakhshi, A. Maleki, and Z. Varzi, “Green, Natural and Low Cost Xanthum Gum Supported Fe3O4 as a Robust Biopolymer Nanocatalyst for the One-Pot Synthesis of 2-Amino-3-Cyano-4H-Pyran Derivatives,”Polycyclic Aromatic Compounds 40, (2020) : 223–41.
  • Z. Hajizadeh and A. Maleki, “Poly (Ethylene Imine)-Modified Magnetic Halloysite Nanotubes: A Novel, Efficient and Recyclable Catalyst for the Synthesis of Dihydropyrano[2,3-c]Pyrazole Derivatives,” Molecular Catalysis 460, (2018): 87–93.
  • A. Maleki, M. Ghassemi, and R. Firouzi-Haji, “Green Multicomponent Synthesis of Four Different Classes of Six-Membered N-Containing and O-Containing Heterocycles Catalyzed by an Efficient Chitosan-Based Magnetic Bionanocomposite,”Pure and Applied Chemistry 90, no. 2 (2018): 387–94.
  • A. Maleki, M. Azizi, and Z. Emdadi, “A Novel Poly(Ethyleneoxide)-Based Magnetic Nanocomposite Catalyst for Highly Efficient Multicomponent Synthesis of Pyran Derivatives,”Green Chemistry Letters and Reviews 11, no. 4 (2018): 573–82.
  • A. Molla, E. Hossain, and S. Hussain, “Multicomponent Domino Reactions: borax Catalyzed Synthesis of Highly Functionalised Pyran-Annulated Heterocycles,”RSC Advances 3, no. 44 (2013): 21517–23.
  • R. Ramesh, J. Jayamathi, C. Karthika, J. G. Malecki, and A. Lalitha, “An Organocatalytic Newer Synthetic Strategy toward the Access of Polyfunctionalized 4H-Pyrans via Multicomponent Reactions,”Polycyclic Aromatic Compounds 40, no. 2 (2020): 502–15.
  • F. Yi, Y. Peng, and G. Song, “Microwave-Assisted Liquid-Phase Synthesis of Methyl 6-Amino-5-Cyano-4-Aryl-2-Methyl-4H-Pyran-3-Carboxylate Using Functional Ionic Liquid as Soluble Support,”Tetrahedron Letters 46, no. 22 (2005): 3931–3.
  • R. M. N. Kalla, M. R. Kim, and I. Kim, “Dibutylamine-Catalysed Efficient One-Pot Synthesis of Biologically Potent Pyrans,”Tetrahedron Letters 56, no. 5 (2015): 717–20.
  • S. Amirnejat, A. Nosrati, R. Peymanfar, and S. Javanshir, “Synthesis and Antibacterial Study of 2-Amino-4H-Pyrans and Pyrans Annulated Heterocycles Catalyzed by Sulfated Polysaccharide-Coated BaFe12O19 Nanoparticles,”Research on Chemical Intermediates 46, no. 7 (2020): 3683–701.

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