A New Basic Ionic Liquid Supported on Magnetite Nanoparticles: An Efficient Phase-Transfer Catalyst for the Green Synthesis of 2-Amino-3-Cyano-4H-Pyrans

References

• M. A. P. Martins, C. P. Frizzo, D. N. Moreira, N. Zanatta, and H. G. Bonacorso, “Ionic Liquids in Heterocyclic Synthesis,”Chemical Reviews 108, no. 6 (2008): 2015–50.
   PubMed Web of Science ®Google Scholar
• K. N. Marsh, J. A. Boxall, and R. Lichtenthaler, “Room Temperature Ionic Liquids and Their mixtures - A Review,”Fluid Phase Equilibria 219, no. 1 (2004): 93–8.
   Web of Science ®Google Scholar
• A. Kokorin, Ionic Liquids: Applications and Perspectives (Rijeka, Croatia: Janeza Trdine, 2012).
   Google Scholar
• L. Rodríguez-Pérez, E. Teuma, A. Falqui, M. Gómez, and P. Serp, “Supported Ionic Liquid Phase Catalysis on Functionalized Carbon Nanotubes,” Chemical Communications, no. 35 (2008): 4201–3.
   PubMed Web of Science ®Google Scholar
• A. Askalany, C. Olkis, E. Bramanti, D. Lapshin, L. Calabrese, E. Proverbio, A. Freni, and G. Santori, “Silica-Supported Ionic Liquids for Heat-Powered Sorption Desalination,”ACS Applied Materials & Interfaces 11, no. 40 (2019): 36497–505.
   PubMed Web of Science ®Google Scholar
• B. B. Polesso, F. L. Bernard, H. Z. Ferrari, E. A. Duarte, F. D. Vecchia, and S. Einloft, “Supported Ionic Liquids as Highly Efficient and Low-Cost Material for CO2/CH4 Separation Process,”Heliyon 5, no. 7 (2019): e02183.
   PubMed Web of Science ®Google Scholar
• S. Rostamizadeh, N. Zekri, and L. Tahershamsi, “Nanosilica-Supported Dual Acidic Ionic Liquid as a Heterogeneous and Reusable Catalyst for the Synthesis of Flavanones under Solvent-Free Conditions,”Chemistry of Heterocyclic Compounds 51, no. 6 (2015): 526–30.
   Web of Science ®Google Scholar
• T. Wang, W. Wang, Y. Lyu, X. Chen, C. Li, Y. Zhang, X. Song, and Y. Ding, “Highly Recyclable Polymer Supported Ionic Liquids as Efficient Heterogeneous Catalysts for Batch and Flow Conversion of CO2 to Cyclic Carbonates,”RSC Advances 7, no. 5 (2017): 2836–41.
   Web of Science ®Google Scholar
• N. Patel, D. Katheriya, H. Dadhania, and A. Dadhania, “Graphene Oxide Supported Dicationic Ionic Liquid: An Efficient Catalyst for the Synthesis of 1-Carbamatoalkyl-2-Naphthols,”Research on Chemical Intermediates 45, no. 11 (2019): 5595–607.
   Web of Science ®Google Scholar
• V. Polshettiwar, R. Luque, A. Fihri, H. Zhu, M. Bouhrara, and J. M. Basset, “Magnetically Recoverable Nanocatalysts,” Chemical Reviews 111, no. 5 (2011): 3036–75.
   PubMed Web of Science ®Google Scholar
• N. Kakesh, S. Sayyahi, and R. Badri, “Magnetic Nanoparticle Coated with Ionic Organic Networks: A Robust Catalyst for Knoevenagel Condensation,”Comptes Rendus Chimie 21, no. 11 (2018): 1023–8.
   Web of Science ®Google Scholar
• Y. Gao, W. Yang, and D. M. Du, “Efficient Organocatalytic Asymmetric Synthesis of 2-Amino-4H-Chromene-3- Carbonitrile Derivatives,” Tetrahedron: Asymmetry 23, no. 5 (2012): 339–44.
   Google Scholar
• Z. Q. Xu, K. Pupek, W. J. Suling, L. Enache, and M. T. Flavin, “Pyranocoumarin, a Novel anti-TB Pharmacophore: Synthesis and Biological Evaluation against Mycobacterium tuberculosis,”Bioorganic & Medicinal Chemistry 14, no. 13 (2006): 4610–26.
   PubMed Web of Science ®Google Scholar
• X. S. Wang, D. Q. Shi, S. J. Tu, and C. S. Yao, “A Convenient Synthesis of 5-Oxo-5,6,7,8-Tetrahydro-4H-Benzo-[b]-Pyran Derivatives Catalyzed by KF-Alumina,”Synthetic Communications 33, no. 1 (2003): 119–26.
   Web of Science ®Google Scholar
• L. M. Wang, J. H. Shao, H. Tian, Y. H. Wang, and B. Liu, “Rare Earth Perfluorooctanoate [RE(PFO)3] Catalyzed One-Pot Synthesis of Benzopyran Derivatives,”Journal of Fluorine Chemistry 127, no. 1 (2006): 97–100.
   Web of Science ®Google Scholar
• S. Gao, C. H. Tsai, C. Tseng, and C. F. Yao, “Fluoride Ion Catalyzed Multicomponent Reactions for Efficient Synthesis of 4H-Chromene and N-Arylquinoline Derivatives in Aqueous Media,”Tetrahedron 64, no. 38 (2008): 9143–9.
   Web of Science ®Google Scholar
• D. Kumar, V. B. Reddy, S. Sharad, U. Dube, and S. Kapur, “A Facile One-Pot Green Synthesis and Antibacterial Activity of 2-Amino-4H-Pyrans and 2-Amino-5-Oxo-5,6,7,8-Tetrahydro-4H-Chromenes,”European Journal of Medicinal Chemistry 44, no. 9 (2009): 3805–9.
   PubMed Web of Science ®Google Scholar
• H. R. Shaterian, M. Arman, and F. Rigi, “Domino Knoevenagel Condensation, Michael Addition, and Cyclization Using Ionic Liquid, 2-Hydroxyethylammonium Formate, as a Recoverable Catalyst,”Journal of Molecular Liquids 158, no. 2 (2011): 145–50.
   Web of Science ®Google Scholar
• 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.
   Web of Science ®Google Scholar
• 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.
   Web of Science ®Google Scholar
• 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.
   Web of Science ®Google Scholar
• O. H. Qareaghaj, S. Mashkouri, M. R. Naimi-Jamal, G. Kauppb, and G. Kaupp, “Ball Milling for the Quantitative and Specific Solvent-Free Knoevenagel Condensation + Michael Addition Cascade in the Synthesis of Various 2-Amino-4-Aryl-3-Cyano-4H-Chromenes without Heating,” RSC Advances 4, no. 89 (2014): 48191–201.
   Web of Science ®Google Scholar
• Y. B. Wagh, Y. A. Tayade, S. A. Padvi, B. S. Patil, N. B. Patil, and D. S. Dalal, “A Cesium Fluoride Promoted Efficient and Rapid Multicomponent Synthesis of Functionalized 2-Amino-3-Cyano-4H-Pyran and Spirooxindole Derivatives,”Chinese Chemical Letters 26, no. 10 (2015): 1273–7.
   Web of Science ®Google Scholar
• K. Niknam, M. Khataminejad, and F. Zeyaei, “Diethylene Glycol-Bis(3-Methylimidazolium) Dihydroxide as a Dicationic Ionic Liquid Catalyst for the Synthesis of 4H-Pyrane Derivatives in Aqueous Medium,”Tetrahedron Letters 57, no. 3 (2016): 361–5.
   Web of Science ®Google Scholar
• J. Tiwari, M. Saquib, S. Singh, F. Tufail, M. Singh, J. Singh, and J. Singh, “Visible Light Promoted Synthesis of Dihydropyrano[2,3-c] Chromenes via a Multicomponent-Tandem Strategy under Solvent and Catalyst Free Conditions,”Green Chemistry 18, no. 11 (2016): 3221–31.
   Web of Science ®Google Scholar
• A. Maleki, M. Aghaei, and N. Ghamari, “Facile Synthesis of Tetrahydrobenzoxanthenones via a One-Pot Three-Component Reaction Using an Eco-Friendly and Magnetized Biopolymer Chitosan-Based Heterogeneous Nanocatalyst,”Applied Organometallic Chemistry 30, no. 11 (2016): 939–42.
   Web of Science ®Google Scholar
• F. Shirini, M. Makhsous, and M. Seddighi, “Introduction of Brönsted Acidic Ionic Liquid Supported on Nanoporous Na+-Montmorillonite as an Efficient Catalyst for the Synthesis of 2-Amino-Tetrahydro-4H-Pyrans,” Iranian Journal of Catalysis 7, (2017): 21–6.
   Web of Science ®Google Scholar
• A. Maleki, and S. Azadegan, “Preparation and Characterization of Silica-Supported Magnetic Nanocatalyst and Application in the Synthesis of 2-Amino-4H-Chromene-3-Carbonitrile Derivatives,”Inorganic and Nano-Metal Chemistry 47, no. 6 (2017): 917–24.
   Web of Science ®Google Scholar
• 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.
   Web of Science ®Google Scholar
• A. Maleki, M. Azizi, and Z. Emdadi, “A Novel Poly(Ethyleneoxide)-Based Magnetic Nanocomposite Catalyst for Highly Efficient Multicomponent Synthesis of Pyran Derivatives Efficient Multicomponent Synthesis of Pyran Derivatives,”Green Chemistry Letters and Reviews 11, no. 4 (2018): 573–82.
   Web of Science ®Google Scholar
• F. Najafi, and M. Fallah-Mehrjardi, “Synthesis of Fe3O4 Nanoparticles Bound with Polyethylene Glycol Substituted 1-Methyl Imidazolium Bromide and Their Application as Nanomagnetic and Recyclable Phase-Transfer Catalysts for the Green and Efficient Synthesis of 4H-Pyrans,”Letters in Organic Chemistry 15, no. 9 (2018): 778–86.
   Web of Science ®Google Scholar
• H. Talaei, M. Fallah-Mehrjardi, and F. Hakimi, “Polyethylene Glycol-(N-Methylimidazolium) Hydroxide-Grafted γ-Fe2O3@HAp: A Novel Nanomagnetic Recyclable Basic Phase-Transfer Catalyst for the Synthesis of Tetrahydrobenzopyran Derivatives in Aqueous Media,”Journal of the Chinese Chemical Society 65, no. 5 (2018): 523–30.
   Web of Science ®Google Scholar
• A. Maleki, Z. Varzi, and F. Hassanzadeh-Afruzi, “Preparation and Characterization of an Eco-Friendly ZnFe2O4@Alginic Acid Nanocomposite Catalyst and Its Application in the Synthesis of 2-Amino-3-Cyano-4H-Pyran Derivatives,” Polyhedron 171, (2019): 193–202.
   Web of Science ®Google Scholar
• A. Maleki, and Z. Hajizadeh, “Magnetic Aluminosilicate Nanoclay: A Natural and Efficient Nanocatalyst for the Green Synthesis of 4H-Pyran Derivatives,”Silicon 11, no. 6 (2019): 2789–98.
   Web of Science ®Google Scholar
• W. Ma, A. G. Ebadi, M. S. Sabil, R. Javahershenas, and G. Jimenez, “One-Pot Synthesis of 2-Amino-4H-Chromene Derivatives by MNPs@Cu as an Effective and Reusable Magnetic Nanocatalyst,”RSC Advances 9, no. 23 (2019): 12801–12.
   PubMed Web of Science ®Google Scholar
• M. Fallah-Mehrjardi, M. Foroughi, and S. H. Banitaba, “Polyethylene Glycol-Bis(N-Methylimidazolium)Dihydroxide as an Efficient and Recyclable Basic Phase-Transfer Catalyst for the Synthesis of 4H-Pyran Derivatives in Aqueous Media,” Asian Journal of Green Chemistry 4, (2020): 75–86.
   Google Scholar
• F. Auria-Luna, V. Fernández-Moreira, E. Marqués-López, M. C. Gimeno, and R. P. Herrera, “Ultrasound-Assisted Multicomponent Synthesis of 4H-Pyrans in Water and DNA Binding Studies,”Scientific Reports 10, no. 1 (2020): 11594–610.
   PubMed Web of Science ®Google Scholar
• A. Amini, S. Sayyahi, S. J. Saghanezhad, and N. Taheri, “Integration of Aqueous Biphasic with Magnetically Recyclable Systems: Polyethylene Glycol-Grafted Fe3O4 Nanoparticles Catalyzed Phenacyl Synthesis in Water,” Catalysis Communications 78, (2016): 11–6.
   Web of Science ®Google Scholar
• M. Z. Kassaee, H. Masrouri, and F. Movahedi, “Sulfamic Acid-Functionalized Magnetic Fe3O4 Nanoparticles as an Efficient and Reusable Catalyst for One-Pot Synthesis of α-Amino Nitriles in Water,”Applied Catalysis A: General 395, no. 1–2 (2011): 28–33.
   Web of Science ®Google Scholar
• A. R. Kiasat, and J. Davarpanah, “Fe3O4@Silica Sulfuric Acid Nanoparticles: An Efficient Reusable Nanomagnetic Catalyst as Potent Solid Acid for One-Pot Solvent-Free Synthesis of Indazolo [2,1-b] Phthalazine-Triones and Pyrazolo [1,2-b] Phthalazine-Diones,” Journal of Molecular Catalysis A: Chemical 373, (2013): 46–54.
   Web of Science ®Google Scholar