Ionic Liquid-Coated Nanoparticles (CaO@SiO₂@BAIL): A Bi-Functional and Environmentally Benign Catalyst for Green Synthesis of Pyridine, Pyrimidine, and Pyrazoline Derivatives

References

• I. Pacheco-Fernández, and V. Pino, “Green Solvents in Analytical Chemistry,” Current Opinion in Green and Sustainable Chemistry 18 (2019): 42–50.
   Web of Science ®Google Scholar
• A. Mobinikhaledi, A. Yazdanipour, and M. Ghashang, “A Green One-Pot Biginelli Synthesis of 3,4-Dihydropyrimidin-2-(1H)-Ones Catalyzed by Novel Aurivillius Nanostructures under Solvent-Free Conditions,” Reaction Kinetics, Mechanisms and Catalysis 119, no. 2 (2016): 511–22.
   Web of Science ®Google Scholar
• B. Maleki, H. Natheghi, R. Tayebee, H. Alinezhad, A. Amiri, S. A. Hossieni, and S. M. M. Nouri, “Synthesis and Characterization of Nanorod Magnetic Co–Fe Mixed Oxides and Its Catalytic Behavior towards One-Pot Synthesis of Polysubstituted Pyridine Derivatives,” Polycyclic Aromatic Compounds 40, no. 3 (2020): 633–43.
   Web of Science ®Google Scholar
• A. Bamoniri, B. B. F. Mirjalilib, and N. Yaghmaeiyan-Mahabadia, “An Environmentally Friendly Approach to the Synthesis of Azo Dyes Based on 2-Naphthol Using kaolin-SO3H Nanoparticles,” Iranian Journal of Catalysis 8, no. 2 (2018): 81–8.
   Web of Science ®Google Scholar
• A. A. Latimer, A. R. Kulkarni, H. Aljama, J. H. Montoya, J. S. Yoo, C. Tsai, F. Abild-Pedersen, F. Studt, and J. K. Nørskov, “Understanding Trends in C-H bond activation in heterogeneous catalysis,” Nature Materials 16, no. 2 (2017): 225–9.
   PubMed Web of Science ®Google Scholar
• Y. Li, Z. Zhang, T. Fan, X. Li, J. Ji, P. Dong, R. Baines, J. Shen, and M. Ye, “Magnetic Core-Shell to Yolk-Shell Structures in Palladium-Catalyzed Suzuki-Miyaura Reactions: Heterogeneous versus Homogeneous Nature,” ChemPlusChem 81, no. 6 (2016): 564–73. [31968926]
   PubMed Web of Science ®Google Scholar
• N. Koukabi, E. Kolvari, A. Khazaei, M. A. Zolfigol, B. Shirmardi-Shaghasemi, and H. R. Khavasi, “Hantzsch Reaction on Free nano-Fe2O3 Catalyst: Excellent Reactivity Combined with Facile Catalyst Recovery and Recyclability,” Chemical Communications (Cambridge, England) 47, no. 32 (2011): 9230–2.
   PubMed Web of Science ®Google Scholar
• D. Wang, and D. Astruc, “The Recent Development of Efficient Earth-Abundant Transition-Metal Nanocatalysts,” Chemical Society Reviews 46, no. 3 (2017): 816–54.
   PubMed Web of Science ®Google Scholar
• M. Hamidinasab, M. A. Bodaghifard, and A. Mobinikhaledi, “Green Synthesis of 1H‐Pyrazolo [1,2‐b] Phthalazine‐2‐Carbonitrile Derivatives Using a New Bifunctional Base–Ionic Liquid Hybrid Magnetic Nanocatalyst,” Applied Organometallic Chemistry 34, no. 2 (2020): e5386..
   Web of Science ®Google Scholar
• C. P. Mehnert, “Supported Ionic Liquid Catalysis,” Chemistry (Weinheim an Der Bergstrasse, Germany) 11, no. 1 (2004): 50–6.
   PubMed Web of Science ®Google Scholar
• H. T. Nguyen, N.-P T. Le, D.-K N. Chau, and P. H. Tran, “New nano-Fe3O4-Supported Lewis Acidic Ionic Liquid as a Highly Effective and Recyclable Catalyst for the Preparation of Benzoxanthenes and Pyrroles under Solvent-Free Sonication,” RSC Advances 8, no. 62 (2018): 35681–8.
   PubMed Web of Science ®Google Scholar
• A. S. Amarasekara, “Acidic Ionic Liquids,” Chemical Reviews 116, no. 10 (2016): 6133–83.
   PubMed Web of Science ®Google Scholar
• H. T. Nguyen, and P. H. Tran, “An Extremely Efficient and Green Method for the Acylation of Secondary Alcohols, Phenols and Naphthols with a Deep Eutectic Solvent as the Catalyst,” RSC Advances 6, no. 100 (2016): 98365–8.
   Web of Science ®Google Scholar
• P. C. Marr, and A. C. Marr, “Ionic Liquid Gel Materials: applications in Green and Sustainable Chemistry,” Green Chemistry 18, no. 1 (2016): 105–28.
   Web of Science ®Google Scholar
• R. K. Sharma, S. Dutta, S. Sharma, R. Zboril, R. S. Varma, and M. B. Gawande, “Fe3O4 (Iron Oxide)-Supported Nanocatalysts: Synthesis, Characterization and Applications in Coupling Reactions,” Green Chemistry 18, no. 11 (2016): 3184–209.
   Web of Science ®Google Scholar
• M. Gholamhosseini-Nazari, S. Esmati, K. D. Safa, A. Khataee, and R. Teimuri-Mofrad, “Fe3O4@ SiO2-BenzIm-Fc [Cl]/ZnCl2: A Novel and Efficient Nano-Catalyst for the One-Pot Three-Component Synthesis of Pyran Annulated Bis-Heterocyclic Scaffolds under Ultrasound Irradiation,” Research on Chemical Intermediates 45, no. 4 (2019): 1841–62.
   Web of Science ®Google Scholar
• A. O. Etim, P. Musonge, and A. C. Eloka‐Eboka, “Effectiveness of Biogenic Waste‐Derived Heterogeneous Catalysts and Feedstock Hybridization Techniques in Biodiesel Production,” Biofuels, Bioproducts and Biorefining 14, no. 3 (2020): 620–49.
   Web of Science ®Google Scholar
• E. Mosaddegh, and A. Hassankhani, “Preparation and Characterization of nano-CaO Based on Eggshell Waste: Novel and Green Catalytic Approach to Highly Efficient Synthesis of Pyrano,” Chinese Journal of Catalysis 35, no. 3 (2014): 351–6.
   Web of Science ®Google Scholar
• A. Mobinikhaledi, H. Moghanian, and M. Ghanbari, “Synthesis and Characterization of Sodium Polyaspartate-Functionalized Silica-Coated Magnetite Nanoparticles: A Heterogeneous, Reusable and Magnetically Separable Catalyst for the Solvent‐Free Synthesis of 2‐Amino‐4H‐Chromene Derivatives,” Applied Organometallic Chemistry 32, no. 3 (2018): e4108.
   Web of Science ®Google Scholar
• H. Vojoudi, A. Badiei, S. Bahar, G. M. Ziarani, F. Faridbod, and M. R. Ganjali, “A New Nano-Sorbent for Fast and Efficient Removal of Heavy Metals from Aqueous Solutions Based on Modification of Magnetic Mesoporous Silica Nanospheres,” Journal of Magnetism and Magnetic Materials 441, (2017): 193–203.
   Web of Science ®Google Scholar
• P. K. Kundu, M. Dhiman, A. Modak, A. Chowdhury, V. Polshettiwar, and D. Maiti, “Palladium Nanoparticles Supported on Fibrous Silica (KCC-1-PEI/Pd): A Sustainable Nanocatalyst for Decarbonylation Reactions,” ChemPlusChem 81, no. 11 (2016): 1142–6.
   PubMed Web of Science ®Google Scholar
• Q. Zhen, R. Li, L. Qi, K. Hu, X. Yao, Y. Shao, and J. Chen, “Nickel (II)-Catalyzed C–C, N–C Cascade Coupling of Ketonitriles into Substituted Pyrroles and Pyridines,” Organic Chemistry Frontiers 7, no. 2 (2020): 286–91.
   Web of Science ®Google Scholar
• D. Azarifar, R. Nejat-Yami, Z. Akrami, F. Sameri, and S. Samadi, “Tetrakis (Acetonitrile) Copper (I) Hexafluorophosphate as an Efficient Catalyst for the Synthesis of Triazolo [1,2-a] Indazole-1,3,8-Trione and 2Hindazolo [2,1-b] Phthalazine-Trione Derivatives,” Letters in Organic Chemistry 9, no. 2 (2012): 128–32.
   Web of Science ®Google Scholar
• D. Azarifar, R. Nejat-Yami, F. Sameri, and Z. Akrami, “Ultrasonic-Promoted One-Pot Synthesis of 4H-Chromenes, Pyrano [2,3-d] Pyrimidines, and 4H-Pyrano [2,3-c] Pyrazoles,” Letters in Organic Chemistry 9, no. 6 (2012): 435–9.
   Web of Science ®Google Scholar
• X. Liu, X. Huang, W. Lin, D. Wang, Y. Diao, H. Li, X. Hui, Y. Wang, A. Xu, D. Wu, et al. “New Aromatic Substituted Pyrazoles as Selective Inhibitors of Human Adipocyte Fatty Acid-Binding Protein,” Bioorganic & Medicinal Chemistry Letters 21, no. 10 (2011): 2949–52.
   PubMed Web of Science ®Google Scholar
• A. R. Trivedi, D. K. Dodiya, N. R. Ravat, and V. H. Shah, “Synthesis and Biological Evaluation of Some New Pyrimidines via a Novel Chalcone Series,” Arkivoc 2008, no. 11 (2008): 131–41.
   Google Scholar
• S. Samshuddin, B. Narayana, D. N. Shetty, and R. Raghavendra, “An Efficient Synthesis of 2,4,6-Triaryl Pyridines and Their Biological Evaluation,” Der Pharma Chemica 3, no. 3 (2011): 232–40.
   Google Scholar
• V. A. Verma, A. R. Saundane, R. S. Meti, R. Shamrao, and V. Katkar, “Synthesis, Biological Evaluation and Docking Studies of Some New Indolyl-Pyridine Containing Thiazolidinone and Azetidinone Analogs,” Polycyclic Aromatic Compounds (2020): 1–15
   Web of Science ®Google Scholar
• A. M. Asiri, M. M. Al-Amari, and S. A. Khan, “Multistep Synthesis and Photophysical Investigation of Novel Pyrazoline, a Heterocyclic D-π-a Chromophore (PTPB) as a Fluorescent Chemosensor for the Detection of Fe3+ Metal Ion,” Polycyclic Aromatic Compounds (2020): 1–15
   Web of Science ®Google Scholar
• D. Vishal, D. Mahendra, and S. Sarita, “Synthesis and Pharmacological Study of Some Novel Pyrimidines,” Der Pharmacia Sinica 3 (2012): 343–8
   Google Scholar
• X. Zhu, Z. Li, C. Jin, L. Xu, Q. Wu, and W. Su, “Mechanically Activated Synthesis of 1,3,5-Triaryl-2-Pyrazolines by High Speed Ball Milling,” Green Chemistry 11, no. 2 (2009): 163–5.
   Web of Science ®Google Scholar
• H. Liu, and X. Gong, “DFT Studies on a Series of Nitramines Containing Pyridine Ring,” Polycyclic Aromatic Compounds 34, no. 5 (2014): 588–605.
   Web of Science ®Google Scholar
• H. Wang, W. Zhao, J. Du, F. Wei, Q. Chen, and X. Wang, “Cationic Organotin Cluster [t‐Bu2Sn (OH)(H2O)]22+ 2OTf−‐Catalyzed One‐Pot Three‐Component Syntheses of 5‐Substituted 1H‐Tetrazoles and 2,4,6‐Triarylpyridines in Water,” Applied Organometallic Chemistry 33, no. 10 (2019): e5132. .
   Web of Science ®Google Scholar
• M. A. Zolfigol, and M. Yarie, “Fe3O4@ TiO2@O2PO2 (CH2)NHSO3H as a Novel Nanomagnetic Catalyst: Application to the Preparation of 2‐Amino‐4, 6‐Diphenylnicotinonitriles via Anomeric‐Based Oxidation,” Applied Organometallic Chemistry 31, no. 5 (2017): e3598.
   Web of Science ®Google Scholar
• M. A. Zolfigol, M. Kiafar, M. Yarie, A. A. Taherpour, and M. Saeidi-Rad, “Experimental and Theoretical Studies of the Nanostructured {Fe3O4@SiO2@(CH2)3Im}C(CN)3 Catalyst for 2-Amino-3-Cyanopyridine Preparation via an Anomeric Based Oxidation,” RSC Advances 6, no. 55 (2016): 50100–11.
   Web of Science ®Google Scholar
• S. P. Gadekar, and M. K. Lande, “Solid Acid Catalyst TS-1 Zeolite-Assisted Solvent-Free One-Pot Synthesis of Poly-Substituted 2,4,6-Triaryl-Pyridines,” Research on Chemical Intermediates 44, no. 5 (2018): 3267–78.
   Web of Science ®Google Scholar
• A. R. Moosavi-Zare, M. A. Zolfigol, S. Farahmand, A. Zare, A. R. Pourali, and R. Ayazi-Nasrabadi, “Synthesis of 2,4,6-Triarylpyridines Using ZrOCl2 under Solvent-Free Conditions,” Synlett 25, no. 02 (2013): 193–6.
   Google Scholar
• M. M. Heravi, K. Bakhtiari, Z. Daroogheha, and F. F. Bamoharram, “An Efficient Synthesis of 2,4,6-Triarylpyridines Catalyzed by Heteropolyacid under Solvent-Free Conditions,” Catalysis Communications 8, no. 12 (2007): 1991–4.
   Web of Science ®Google Scholar
• M. M. Heravi, S. Y. S. Beheshtiha, M. Dehghani, and N. Hosseintash, “Using Magnetic Nanoparticles Fe3O4 as a Reusable Catalyst for the Synthesis of Pyran and Pyridine Derivatives via One-Pot Multicomponent Reaction,” Journal of the Iranian Chemical Society 12, no. 11 (2015): 2075–81.
   Web of Science ®Google Scholar
• F. Sameri, A. Mobinikhaledi, and M. A. Bodaghifard, “High-Efficient Synthesis of 2-Imino-2 H-Chromenes and Dihydropyrano [c] Chromenes Using Novel and Green Catalyst (CaO@ SiO2@AIL),” Research on Chemical Intermediates 47, no. 2 (2021): 723–41.
   Web of Science ®Google Scholar
• A. Mobinikhaledi, H. Moghanian, B. Ajerloo, and F. Dousti, “Synthesis and Characterization of Silica‐Coated Magnetite Nanoparticles Modified with Bis (Pyrazolyl) Triazine Ruthenium (II) Complex and the Application of These Nanoparticles as a Highly Efficient Catalyst for the Hydrogen Transfer Reduction of Ketones,” Applied Organometallic Chemistry 34, no. 2 (2020): e5366.
   Web of Science ®Google Scholar
• R. Ghorbani-Vaghei, and N. Sarmast, “Hexamethylenetetramine Grafted Layered Double Hydroxides as a Novel and Green Heterogeneous Ionic Liquid Catalyst for the Synthesis of Pyrido [2,3-d] Pyrimidine Derivatives,” Research on Chemical Intermediates 44, no. 7 (2018): 4483–501.
   Web of Science ®Google Scholar
• W. Stöber, A. Fink, and E. Bohn, “Controlled Growth of Monodisperse Silica Spheres in the Micron Size Range,” Journal of Colloid and Interface Science 26, no. 1 (1968): 62–9.
   Web of Science ®Google Scholar
• F. Sameri, A. Mobinikhaledi, and M. A. Bodaghifard, “Preparation of Core/Shell CaO@ SiO2-SO3H as a Novel and Recyclable Nanocatalyst for One-Pot Synthesize of Dihydropyrano [2,3-c] Pyrazoles and Tetrahydrobenzo [b] Pyrans,” Silicon (2021): 1–12
   Web of Science ®Google Scholar
• P. R. Pandit, and M. Fulekar, “Egg Shell Waste as Heterogeneous Nanocatalyst for Biodiesel Production: Optimized by Response Surface Methodology,” Journal of Environmental Management 198, no. Pt 1 (2017): 319–29.
   PubMedGoogle Scholar
• D. S. Rekunge, I. A. Kale, and G. U. Chaturbhuj, “An Efficient, Green Solvent-Free Protocol for the Synthesis of 2,4,6-Triarylpyridines Using Reusable Heterogeneous Activated Fuller’s Earth Catalyst,” Journal of the Iranian Chemical Society 15, no. 11 (2018): 2455–62.
   Web of Science ®Google Scholar
• M. A. Zolfigol, F. Karimi, M. Yarie, and M. Torabi, “Catalytic Application of Sulfonic Acid‐Functionalized Titana‐Coated Magnetic Nanoparticles for the Preparation of 1,8‐Dioxodecahydroacridines and 2,4,6‐Triarylpyridines via Anomeric‐Based Oxidation,” Applied Organometallic Chemistry 32, no. 2 (2018): e4063.
   Web of Science ®Google Scholar
• M. Adib, B. Mohammadi, S. Rahbari, and P. Mirzaei, “Reaction between Guanidine Hydrochloride and Chalcones: An Efficient Solvent-Free Synthesis of 2,4,6-Triarylpyridines under Microwave Irradiation,” Chemistry Letters 37, no. 10 (2008): 1048–9.
   Web of Science ®Google Scholar
• T. Kobayashi, H. Kakiuchi, and H. Kato, “On the Reaction of N-(Diphenylphosphinyl)-1-Phenylethanimine with Aromatic Aldehydes Giving 4-Aryl-2,6-Diphenylpyridine Derivatives,” Bulletin of the Chemical Society of Japan 64, no. 2 (1991): 392–5.
   Web of Science ®Google Scholar
• M. Wang, Z. Yang, Z. Song, and Q. Wang, “Three‐Component One‐Pot Synthesis of 2,4,6‐Triarylpyridines without Catalyst and Solvent,” Journal of Heterocyclic Chemistry 52, no. 3 (2015): 907–10.
   Web of Science ®Google Scholar
• M. Adib, H. Tahermansouri, S. A. Koloogani, B. Mohammadi, and H. R. Bijanzadeh, “Kröhnke Pyridines: An Efficient Solvent-Free Synthesis of 2,4,6-Triarylpyridines,” Tetrahedron Letters 47, no. 33 (2006): 5957–60.
   Web of Science ®Google Scholar
• S. S. Mansoor, K. Aswin, K. Logaiya, and S. Sudhan, “[Bmim] BF4 Ionic Liquid: An Efficient Reaction Medium for the One-Pot Multi-Component Synthesis of 2-Amino-4, 6-Diphenylpyridine-3-Carbonitrile Derivatives,” Journal of Saudi Chemical Society 20, no. 5 (2016): 517–22.
   Web of Science ®Google Scholar
• F. Shi, S. Tu, F. Fang, and T. Li, “One-Pot Synthesis of 2-Amino-3-Cyanopyridine Derivatives under Microwave Irradiation without Solvent,” Arkivoc 1, no. 1 (2005): 137–42.
   Web of Science ®Google Scholar
• S. M. Siddiqui, and A. Azam, “Synthesis, Characterization of 4,6-Disubstituted Aminopyrimidines and Their Sulphonamide Derivatives as anti-Amoebic Agents,” Medicinal Chemistry Research 23, no. 6 (2014): 2976–84.
   Web of Science ®Google Scholar
• S. Saikia, and R. Borah, “One‐Pot Sequential Synthesis of 2‐Amino‐4, 6‐Diaryl Pyrimidines Involving SO3H‐Functionalized Piperazinium‐Based Dicationic Ionic Liquids as Homogeneous Catalysts,” ChemistrySelect 4, no. 30 (2019): 8751–6.
   Web of Science ®Google Scholar
• F. H. Al-Hajjar, Y. A. Al-Farkh, and H. S. Hamoud, “Synthesis and Spectroscopic Studies of the Pyrimidine-2 (1H) Thione Derivatives,” Canadian Journal of Chemistry 57, no. 20 (1979): 2734–42.
   Web of Science ®Google Scholar
• S. Fandakli, N. Kahriman, T. Beyza Yücel, Ş. Alpay Karaoğlu, and N. Yayli, “Biological Evaluation and Synthesis of New Pyrimidine-2 (1H)-ol/-Thiol Derivatives Derived from Chalcones Using the Solid Phase Microwave Method,” Turkish Journal of CHEMISTRY 42, no. 2 (2018): 520–35.
   Web of Science ®Google Scholar
• S. Narwal, S. Kumar, and P. K. Verma, “Design, Synthesis and Antimicrobial Evaluation of Pyrimidin-2-ol/Thiol/Amine Analogues,” Chemistry Central Journal 11, no. 1 (2017): 52.
   PubMedGoogle Scholar
• A. Shaabani, A. Rahmati, B. Aghaaliakbari, and J. Safaei‐Ghomi, “1,1,3,3‐N,N,N′,N′‐Tetramethylguanidinium Trifluoroacetate Ionic Liquid–Promoted Efficient One‐Pot Synthesis of Trisubstituted Imidazoles,” Synthetic Communications 36, no. 1 (2006): 65–70.
   Web of Science ®Google Scholar
• L. D. Santos Bubniak, P. C. Gaspar, A. C. R. de Moraes, A. Bigolin, R. K. de Souza, F. C. Buzzi, R. Corrêa, V. C. Filho, L. C. Bretanha, G. A. Micke, et al. “Effects of 1,3,5-Triphenyl-4,5-Dihydro-1H-Pyrazole Derivatives on Cell-Cycle and Apoptosis in Human Acute Leukemia Cell Lines,” Canadian Journal of Physiology and Pharmacology 95, no. 5 (2017): 548–63.
   PubMed Web of Science ®Google Scholar
• J.-T. Li, X.-H. Zhang, and Z.-P. Lin, “An Improved Synthesis of 1,3,5-Triaryl-2-Pyrazolines in Acetic Acid Aqueous Solution Under Ultrasound Irradiation,” Beilstein Journal of Organic Chemistry 3, no. 1 (2007): 13.
   PubMedGoogle Scholar