Binding of Polyethylene Glycol Imidazolium Hydrogen Sulfate to Magnetic Nanoparticles and Its Application as a Novel Recyclable Solid Acid Catalyst in the Friedländer Synthesis of Quinolines under Solvent-Free Conditions

References

• Marcos A. P. Martins, Clarissa P. Frizzo, Dayse N. Moreira, Nilo Zanatta, and Helio G. Bonacorso, “Ionic Liquids in Heterocyclic Synthesis,” Chemical Reviews 108, no. 6 (2008): 2015–50.
   PubMed Web of Science ®Google Scholar
• Kenneth N. Marsh, John A. Boxall, and Ruediger Lichtenthaler, “Room Temperature Ionic Liquids and Their mixtures - A Review,” Fluid Phase Equilibria 219, no. 1 (2004): 93–8.
   Web of Science ®Google Scholar
• Alexander Kokorin. Ionic Liquids: Applications and Perspectives. Rijeka, Croatia: Janeza Trdine; (2012).
   Google Scholar
• Vincenzo Campisciano, Francesco Giacalone, and Michelangelo Gruttadauria, “Supported Ionic Liquids: A Versatile and Useful Class of Materials,” Chemical Record (New York, N.Y.) 17, no. 10 (2017): 918–38.
   PubMed Web of Science ®Google Scholar
• Yuyao Huang, Yuanlong Xiao, Hongliang Huang, Ziping Liu, Dahuan Liu, Qingyuan Yang, and Chongli Zhong, “Ionic Liquid Functionalized Multi-Walled Carbon Nanotubes/Zeolitic Imidazolate Framework Hybrid Membranes for Efficient H2/CO2 Separation,” Chemical Communications (Cambridge, England) 51, no. 97 (2015): 17281–4.
   PubMed Web of Science ®Google Scholar
• Ahmed Askalany, Christopher Olkis, Emilia Bramanti, Dmitry Lapshin, Luigi Calabrese, Edoardo Proverbio, Angelo Freni, and Giulio 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
• Bárbara B. Polesso, Franciele L. Bernard, Henrique Z. Ferrari, Evandro A. Duarte, Felipe Dalla Vecchia, and Sandra 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
• Shahnaz Rostamizadeh, Negar Zekri, and Leili 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
• Tao Wang, Wenlong Wang, Yuan Lyu, Xingkun Chen, Cunyao Li, Yan Zhang, Xiangen Song, and Yunjie 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
• Nipun Patel, Deepak Katheriya, Harsh Dadhania, and Abhishek 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
• Yu Lin Hu, and Dong Fang, “Preparation of Silica Supported Ionic Liquids for Highly Selective Hydroxylation of Aromatics with Hydrogen Peroxide under Solvent-Free Conditions,” Journal of the Mexican Chemical Society 60, no. 4 (2016): 207–17.
   Web of Science ®Google Scholar
• Bahman Tamami, Alireza Sardarian, and Elaheh Ataollahi, “Synthesis and Application of Polyvinylimidazole-Based Brønsted Acidic Ionic Liquid Grafted Silica as an Efficient Heterogeneous Catalyst in the Preparation of Quinoxaline Derivatives,” Turkish Journal of Chemistry 40, (2016) : 422–33.
   Web of Science ®Google Scholar
• Sharanabasappa Khanapure, Megha Jagadale, Dolly Kale, Shivanand Gajare, and Gajanan Rashinkar, “Cellulose-Supported Ionic Liquid Phase Catalyst-Mediated Mannich Reaction,” Australian Journal of Chemistry 72, no. 7 (2019): 513–23.
   Web of Science ®Google Scholar
• Vivek Polshettiwar, Rafael Luque, Aziz Fihri, Haibo Zhu, Mohamed Bouhrara, and Jean Marie Basset, “Magnetically Recoverable nanocatalysts,” Chemical Reviews 111, no. 5 (2011): 3036–75.
   PubMed Web of Science ®Google Scholar
• Rezvan Kardooni, and Ali Reza Kiasat, “Bifunctional PEG/NH2 Silica-Coated Magnetic Nanocomposite: An Efficient and Recoverable Core–Shell-Structured Catalyst for One Pot Multicomponent Synthesis of 3-Alkylated Indoles via Yonemitsu-Type Condensation,” Journal of the Taiwan Institute of Chemical Engineers 87, (2018): 241–51.
   Web of Science ®Google Scholar
• Mahsa Bagheri, Majid Masteri-Farahani, and Melika Ghorbani, “Synthesis and Characterization of Heteropolytungstate-Ionic Liquid Supported on the Surface of Silica Coated Magnetite Nanoparticles,” Journal of Magnetism and Magnetic Materials 327, (2013): 58–63.
   Web of Science ®Google Scholar
• Charu Garkoti, Javaid Shabir, and Subho Mozumdar, “An Imidazolium Based Ionic Liquid Supported on Fe3O4@SiO2 Nanoparticles as an Efficient Heterogeneous Catalyst for N-Formylation of Amines,” New Journal of Chemistry 41, no. 17 (2017): 9291–8.
   Web of Science ®Google Scholar
• Arash Ghorbani-Choghamarani, Zahra Taherinia, and Mohsen Nikoorazm, “Ionic Liquid Supported on Magnetic Nanoparticles as a Novel Reusable Nanocatalyst for the Efficient Synthesis of Tetracyclic Quinazoline Compounds,” Research on Chemical Intermediates 44, no. 11 (2018): 6591–604.
   Web of Science ®Google Scholar
• K. Tanaka, and F. Toda, “Solvent-Free Organic Synthesis,” Chemical Reviews 100, no. 3 (2000): 1025–74.
   PubMed Web of Science ®Google Scholar
• Maya Shankar Singh, and Sushobhan Chowdhury, “Recent Developments in Solvent-Free Multicomponent Reactions: A Perfect Synergy for Eco-Compatible Organic Synthesis,” RSC Advances 2, no. 11 (2012): 4547–92.
   Web of Science ®Google Scholar
• Sainath Zangade, and Pravinkumar Patil, “A Review on Solvent-Free Methods in Organic Synthesis,” Current Organic Chemistry 23, no. 21 (2020): 2295–318.
   Web of Science ®Google Scholar
• Mahesh Akula, Jonnalagadda Padma Sridevi, P. Yogeeswari, D. Sriram, and Anupam Bhattacharya, “New Class of Antitubercular Compounds: Synthesis and anti-Tubercular Activity of 4-Substituted Pyrrolo[2,3-c]Quinolines,” Monatshefte Für Chemie - Chemical Monthly 145, no. 5 (2014): 811–9.
   Google Scholar
• Sandeep Singh, Gurpuneet Kaur, Veenu Mangla, and Manish K. Gupta, “Quinoline and Quinolones: Promising Scaffolds for Future Antimycobacterial Agents,” Journal of Enzyme Inhibition and Medicinal Chemistry 30, no. 3 (2015): 492–504.
   PubMed Web of Science ®Google Scholar
• Obaid Afzal, Suresh Kumar, Md Rafi Haider, Md Rahmat Ali, Rajiv Kumar, Manu Jaggi, and Sandhya Bawa, “A Review on Anticancer Potential of Bioactive Heterocycle Quinoline,” European Journal of Medicinal Chemistry 97, (2015) : 871–910.
   PubMed Web of Science ®Google Scholar
• Himank Kumar, Vinod Devaraji, Ritika Joshi, Manojkumar Jadhao, Piyush Ahirkar, R. Prasath, P. Bhavana, and Sujit Kumar Ghosh, “Antihypertensive Activity of a Quinoline Appended Chalcone Derivative and Its Site Specific Binding Interaction with a Relevant Target Carrier Protein,” RSC Advances 5, no. 80 (2015): 65496–513.
   Web of Science ®Google Scholar
• Peng Teng, Chunhui Li, Zhong Peng, Vanderschouw Anne Marie, Alekhya Nimmagadda, Ma Su, Yaqiong Li, Xingmin Sun, and Jianfeng Cai, “Facilely Accessible Quinoline Derivatives as Potent Antibacterial Agents,” Bioorganic & Medicinal Chemistry 26, no. 12 (2018): 3573–9.
   PubMed Web of Science ®Google Scholar
• Chia-Chung Cheng and Shou-Jen Yan, “The Friedländer Synthesis of Quinolines,” Organic Reactions 28, (1982): 37–201.
   Web of Science ®Google Scholar
• Mehdi Fallah-Mehrjardi, “Friedlander Synthesis of Poly-Substituted Quinolines: A Mini Review,” Mini-Reviews in Organic Chemistry 14, no. 3 (2017): 187–96.
   Web of Science ®Google Scholar
• Ali Reza Kiasat and Mehdi Fallah-Mehrjardi, “B(HSO4)3: A Novel and Efficient Solid Acid Catalyst for the Regioselective Conversion of Epoxides to Thiocyanohydrins under Solvent-Free Conditions,” Journal of the Brazilian Chemical Society 19, no. 8 (2008): 1595–9.
   Web of Science ®Google Scholar
• Ali Reza Kiasat and Mehdi Fallah-Mehrjardi, “Dowex as Reusable Acidic Polymeric Catalyst in the Efficient and Regioselective Conversion of Epoxides into β-Hydroxy Thiocyanates under Solvent Free Conditions,” Journal of the Chinese Chemical Society 55, no. 5 (2008): 1119–24.
   Web of Science ®Google Scholar
• Ali Reza Kiasat and Mehdi Fallah-Mehrjardi, “Melamine Sulfonic Acid: A Recoverable Catalyst for the Ecofriendly Synthesis of Thiocyanohydrins under Solvent-Free Conditions,” Synthetic Communications 40, no. 10 (2010): 1551–8.
   Web of Science ®Google Scholar
• Monire Beyki and Mehdi Fallah-Mehrjardi, “Silica Sulfuric Acid-Coated Fe3O4 Nanoparticles as a Highly Efficient and Reusable Solid Acid Catalyst for the Green Synthesis of 2,3-Dihydroquinazolin-4(1H)-Ones under Solvent-Free Conditions,” Letters in Organic Chemistry 15, no. 1 (2017): 39–44.
   Web of Science ®Google Scholar
• Ali Reza Kiasat, and Jamal 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
• Atefeh Amini, Soheil Sayyahi, Seyyed Jafar Saghanezhad, and Narges 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, Hassan Masrouri, and Farnaz 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
• Surya K. De, and Richard A. Gibbs, “A Mild and Efficient One-Step Synthesis of Quinolines,” Tetrahedron Letters 46, no. 10 (2005): 1647–9.
   Web of Science ®Google Scholar
• Ahmad Shaabani, Ebrahim Soleimani, and Zahra Badri, “Silica Sulfuric Acid as an Inexpensive and Recyclable Solid Acid Catalyzed Efficient Synthesis of Quinolines,” Monatshefte Für Chemie - Chemical Monthly 137, no. 2 (2006): 181–4.
   Google Scholar
• D. Subhas Bose, and Racherla Kishore Kumar, “An Efficient, High Yielding Protocol for the Synthesis of Functionalized Quinolines via the Tandem Addition/Annulation Reaction of o-Aminoaryl Ketones with α-Methylene Ketones,” Tetrahedron Letters 47, no. 5 (2006): 813–6.
   Web of Science ®Google Scholar
• Minoo Dabiri, Mostafa Baghbanzadeh, and Maryam S. Nikcheh, “Oxalic Acid: An Efficient and Cost-Effective Organic Catalyst for the Friedländer Quinoline Synthesis under Solvent-Free Conditions,” Monatshefte Für Chemie - Chemical Monthly 138, no. 12 (2007): 1249–52.
   Google Scholar
• Ahmad Shaabani, Abbas Rahmati, and Zahra Badri, “Sulfonated Cellulose and Starch: New Biodegradable and Renewable Solid Acid Catalysts for Efficient Synthesis of Quinolines,” Catalysis Communications 9, no. 1 (2008): 13–6.
   Web of Science ®Google Scholar
• Minoo Dabiri and Sahareh Bashiribod, “Phosphotungstic Acid: An Efficient, Cost-Effective and Recyclable Catalyst for the Synthesis of Polysubstituted Quinolines,” Molecules (Basel, Switzerland) 14, no. 3 (2009): 1126–33.
   PubMed Web of Science ®Google Scholar
• Sodeh Sadjadi, Soudeh Shiri, Rahim Hekmatshoar, and Yahya S. Beheshtiha, “Nanocrystalline Aluminium Oxide: A Mild and Efficient Reusable Catalyst for the One-Pot Synthesis of Poly-Substituted Quinolines via Friedlander Hetero-Annulation,” Monatshefte Für Chemie - Chemical Monthly 140, no. 11 (2009): 1343–7.
   Google Scholar
• Ali Reza Kiasat, Arash Mouradzadegun, and Seyyed Jafar Saghanezhad, “Poly(4-Vinylpyridinium Butane Sulfonic Acid) Hydrogen Sulfate: An Efficient, Heterogeneous Poly(Ionic Liquid), Solid Acid Catalyst for the One-Pot Preparation of 1-Amidoalkyl-2-Naphthols and Substituted Quinolines under Solvent-Free Conditions,” Chinese Journal of Catalysis 34, no. 10 (2013): 1861–8.
   Web of Science ®Google Scholar
• Monire Beyki and Mehdi Fallah-Mehrjardi, “Fe3O4@SiO2-SO3H as a Recyclable Heterogeneous Nanomagnetic Catalyst for the One-Pot Synthesis of Substituted Quinolines via Friedländer Heteroannulation under Solvent-Free Conditions,” Iranian Chemical Communication 5, (2017): 484–93.
   Web of Science ®Google Scholar