Amino Functionalized Nano Fe₃O₄@SiO₂ as a Magnetically Green Catalyst for the One-Pot Synthesis of Spirooxindoles Under Mild Conditions

References

• Deng, J., L. P. Mo, F. Y. Zhao, L. L. Hou, L. Yang, and Z. H. Zhang. “Sulfonic Acid Supported on Hydroxyapatite-Encapsulated-γ-Fe2O3 Nanocrystallites as a Magnetically Separable Catalyst for One-Pot Reductive Amination of Carbonyl Compounds.” Green Chem. 9 (2011): 2576–84.
   Google Scholar
• Liu, Y. H., J. Deng, J. W. Gao, and Z. H. Zhang. “Triflic Acid‐Functionalized Silica‐Coated Magnetic Nanoparticles as a Magnetically Separable Catalyst for Synthesis of Gem‐Dihydroperoxides.” Adv. Synth. Catal. 2208; 3 (2012): 441–47.
   Google Scholar
• Gawande, M. B., A. K. Rathi, I. D. Nogueira, R. S. Varma, and P. S. Branco. “Magnetite-Supported Sulfonic Acid: A Retrievable Nanocatalyst for the Ritter Reaction and Multicomponent Reactions.” Green Chem. 7 (2013): 1895–99.
   Google Scholar
• Deng, Y. H., D. W. Qi, C. H. Deng, X. M. Zhang, and D. Y. Zhao. “Superparamagnetic High-Magnetization Microspheres with an Fe3O4@ SiO2 Core and Perpendicularly Aligned Mesoporous SiO2 Shell for Removal of Microcystins.” J. Am. Chem. Soc. 1 (2008): 28–29.
   Google Scholar
• Wang, D., and D. Astruc. “Fast-Growing Field of Magnetically Recyclable Nanocatalysts.” Chem. Rev. 14 (2014): 6949–85.
   Google Scholar
• Polshettiwar, V., R. Luque, A. Fihri, H. Zhu, M. Bouhrara, J. M. Basset. “Magnetically Recoverable Nanocatalysts.” Chem. Rev. 111 (2011): 3036–75.
   PubMed Web of Science ®Google Scholar
• Gawande, M. B., P. S. Branco, R. S. Varma. “Nano-magnetite (Fe3O4) as a Support for Recyclable Catalysts in the Development of Sustainable Methodologies.” Chem. Soc. Rev. 42 (2013): 3371–93.
   PubMed Web of Science ®Google Scholar
• Maleki, A. “Fe3O4/SiO2 Nanoparticles: An Efficient and Magnetically Recoverable Nanocatalyst for the One-Pot Multicomponent Synthesis of Diazepines.” Tetrahedron 68 (2012): 7827–33.
   Web of Science ®Google Scholar
• Maleki, A. “One-Pot Multicomponent Synthesis of Diazepine Derivatives using Terminal Alkynes in the Presence of Silica-Supported Superparamagnetic Iron Oxide Noparticles.” Tetrahedron Lett. 54 (2013): 2055–59.
   Web of Science ®Google Scholar
• Maleki, A. “One-Pot Three-Component Synthesis of Pyrido[2′,1′:2,3]imidazo[4,5-c]isoquinolines using Fe3O4@SiO2–OSO3H as an Efficient Heterogeneous Nanocatalyst.” RSC Adv. 4 (2014): 64169–73.
   Web of Science ®Google Scholar
• Maleki, A., and M. Kamalzare. “Fe3O4@cellulose Composite Nanocatalyst: Preparation, Characterization and Application in the Synthesis of Benzodiazepines.” Catal. Commun. 53 (2014): 67–71.
   Web of Science ®Google Scholar
• Maleki, A., Z. Alirezvani, and S. Maleki. “Design, Preparation and Characterization of Urea-Functionalized Fe3O4/SiO2 Magnetic Nanocatalyst and Application for the One-Pot Multicomponent Synthesis of Substituted Imidazole Derivatives.” Catal. Commun. 69 (2015): 29–33.
   Web of Science ®Google Scholar
• Maleki, A., M. Aghaei, and N. Ghamari. “Synthesis of Benzimidazolo[2,3-b]quinazolinone Derivatives via a One-Pot Multicomponent Reaction Promoted by a Chitosan-Based Composite Magnetic Nanocatalyst.” Chem. Lett. 44 (2015): 259–61.
   Web of Science ®Google Scholar
• Huh, Y. M., Y. W. Jun, H. T. Song, S. Kim, J. S. Choi, J. H. Lee, S. Yoon, K. S. Kim, J. S. Shin, J. S. Suh, and J. Cheon. “In Vivo Magnetic Resonance Detection of Cancer by Using Multifunctional Magnetic Nanocrystals.” J. Am. Chem. Soc. 35 (2005): 12387–91.
   Google Scholar
• Li, P. H., B. L. Li, L. P. Mo, N. Liu, H. J. Kang, Y. N. Liu, and Z. H. Zhang. “A Recyclable Magnetic Nanoparticles Supported Antimony Catalyst for the Synthesis of N-Substituted Pyrroles in Water.” Appl. Catal. A: Gen. 457 (2013): 34–41.
   Web of Science ®Google Scholar
• Yoon, T. J., K. N. Yu, E. Kim, J. S. Kim, B. G. Kim, S. H. Yun, B. H. Sohn, M. H. Cho, J. K. Lee, and S. B. Park. “Specific Targeting, Cell Sorting, and Bioimaging with Smart Magnetic Silica Core–Shell Nanomaterials.” Small 2 (2006): 209–15.
   PubMed Web of Science ®Google Scholar
• Yi, D. K., S. S. Lee, and J. Y. Ying. “Synthesis and Applications of Magnetic Nanocomposite Catalysts.” Chem. Mater. 10 (2006): 2459–61.
   Google Scholar
• Xu, Z. P., Q. H. Zeng, G. Q. Lu, and A. B. Yu “Inorganic Nanoparticles as Carriers for Efficient Cellular Delivery.” Chem. Eng. Sci. 3 (2006): 1027–40.
   Google Scholar
• Wang, J., S. Zheng, Y. Shao, J. Liu, Z. Xu, and D. Zhu. “Amino-Functionalized Fe3O4@SiO2 Core–Shell Magnetic Nanomaterial as a Novel Adsorbent for Aqueous Heavy Metals Removal.” J. Colloid Interface Sci. 1 (2010): 293–99.
   Google Scholar
• Dong, Z., X. Tian, Y. Chen, Y. Guo, and J. Ma. “Dansyl Derivative Functionalized Fe3O4@SiO2 Fluorescent Probe for Detection and Removal of Hg2+ in Aqueous Solution.” RSC Adv. 4 (2013): 1082–88.
   Google Scholar
• Cocco, C. M. T., C. Congiu, V. Lilliu, and V. Onnis. “Synthesis and in Vitro Antitumoral Activity of New 3, 5-Dicyanopyridine Derivatives.” Bioorg. Med. Chem. 4 (2007): 1859–67.
   Web of Science ®Google Scholar
• Gawande, M. B., A. Velhinho, I. D. Nogueira, C. A. A. Ghumman, O. M. N. D. Teodoro, and P. S. Branco. “A Facile Synthesis of Cysteine–Ferrite Magnetic Nanoparticles for Application in Multicomponent Reactions—a Sustainable Protocol.” RSC Adv. 15 (2012): 6144–49.
   Google Scholar
• Kiasat, A. R., 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.” J. Mol. Cat. A: Chem. 373 (2013): 46–54.
   Web of Science ®Google Scholar
• Shaterian, H. R., M. Ghashang, and M. Feyzi. “Silica Sulfuric Acid as an Efficient Catalyst for the Preparation of 2h-Indazolo [2, 1-B] Phthalazine-Triones.” Appl. Catal. A: Gen. 2 (2008): 128–33.
   Google Scholar
• Shinde, P. V., V. B. Labade, B. B. Shingate, and M. S. Shingare. “Application of Unmodified Microporous Molecular Sieves for the Synthesis of Poly Functionalized Pyridine Derivatives in Water.” J. Mol. Catal. A: Chem. 1 (2011): 100–05.
   Google Scholar
• Sun, S., and H. Zeng. “Size-Controlled Synthesis of Magnetite Nanoparticles.” J. Am. Chem. Soc. 28 (2002): 8204–05.
   Google Scholar
• Sivakami, R., S. Ganesh Babu, S. Dhanuskodi, and R. Karvembu. “Magnetically Retrievable Lepidocrocite Supported Copper Oxide Nanocatalyst (Fe–Cuo) for N-Arylation of Imidazole.” RSC Adv. 12 (2015): 8571–78.
   Google Scholar
• Fujioka, H., K. Murai, O. Kubo, Y. Ohba, and Y. Kita. “New Three-Component Reaction: Novel Formation of a Seven-Membered Ring by the Unexpected Reaction at the Γ-Position of the Β-Keto Ester.” Org. Lett. 9 (2007): 1687–90.
   PubMed Web of Science ®Google Scholar
• Sheldon, R. A. “Green Solvents for Sustainable Organic Synthesis: State of the Art.” Green Chem. 5 (2005): 267–78.
   Google Scholar
• Safaei-Ghomi, J., R. Teymuri, and A. Ziarati. “A Green Synthesis of 3, 4-Dihydropyrimidine-2 (1H)-One/Thione Derivatives Using Nanosilica-Supported Tin (II) Chloride as a Heterogeneous Nanocatalyst.” Monatsh. Chem. 12 (2013): 1865–70.
   Google Scholar
• Nefzi, A., J. M. Ostresh, and R. A. Houghten. “The Current Status of Heterocyclic Combinatorial Libraries.” Chem. Rev. 2 (1997): 449–72.
   Google Scholar
• Ding, K., Y. Lu, Z. Nikolovska-Coleska, S. Qiu, Y.-S. Ding, W. Gao, J. Stuckey, K. Krajewski, P. P. Roller, Y. Tomita, D. A. Parrish, J. R. Deschamps, and S.-M. Wang. “Structure-Based Design of Potent Non-Peptide Mdm2 Inhibitors.” J. Am. Chem. Soc. 29 (2005): 10130–31.
   Google Scholar
• Yeung, B. K. S., B. Zou, M. Rottmann, S. B. Lakshminarayana, S. H. Ang, S. Y. Leong, J. Tan, J. Wong, S. Keller-Maerki, C. Fischli, A. Goh, E. K. Schmitt, P. Krastel, E. Francotte, K. Kuhen, D. Plouffe, K. Henson, T. Wagner, E. A. Winzeler, F. Petersen, B. Reto, V. Dartois, T. Diagana, and T. H. T. Keller. “Spirotetrahydro Β-Carbolines (Spiroindolones): A New Class of Potent and Orally Efficacious Compounds for the Treatment of Malaria.” J. Med. Chem. 14 (2010): 5155–64.
   Google Scholar
• Lundahl, K., J. Schut, J. L. M. A. Schlatmann, G. B. Paerels, and A. Peters. “Synthesis and Antiviral Activities of Adamantane Spiro Compounds. 1. Adamantane and Analogous Spiro-3′-Pyrrolidines.” J. Med. Chem. 2 (1972): 129–32.
   Google Scholar
• Thangamani, A. “Regiospecific Synthesis and Biological Evaluation of Spirooxindolopyrrolizidines via [3+2] Cycloaddition of Azomethine Ylide.” Eur. J. Med. Chem. 12 (2010): 6120–26.
   Google Scholar
• Wang, G. D., X. N. Zhang, and Z. H. Zhang. “One‐Pot Three‐Component Synthesis of Spirooxindoles Catalyzed by Hexamethylenetetramine in Water.” J. Heterocyclic Chem. 1 (2013): 61–65.
   Google Scholar
• Ghahremanzadeh, R., F. Fereshtehnejad, Z. Yasaei, T. Amanpour, and A. Bazgir. “One‐Pot and Three‐Component Synthesis of Spiro [Chromeno [2, 3‐d] Pyrimidine‐5, 3′‐Indoline]‐Diones and Spiro [Chromeno [2, 3‐C] Pyrazole‐4, 3′‐Indoline]‐Diones.” J. Heterocyclic Chem. 4 (2010): 967–72.
   Google Scholar
• Matsumaru, T., M. E. Mc Callum, J. A. Enquist, Jr, G. M. Smith, K. Kong, and J. L. Wood. “Synthetic Studies toward the Citrinadins: Enantioselective Preparation of an Advanced Spirooxindole Intermediate.” Tetrahedron 27 (2014): 4089–93.
   Google Scholar
• Zou, B., C. Chen, S. Y. Leong, M. Ding, and P. W. Smith. “An Efficient Synthesis of 4, 6-Dihydrospiro [Azepino [4, 3, 2-Cd] Indole-3, 3′-Indoline]-2′, 5 (1H)-Diones via Multi-Component Reaction.” Tetrahedron 3 (2014): 578–82.
   Google Scholar
• Feng, J., K. Ablajan, and A. Sali. “4-Dimethylaminopyridine-Catalyzed Multi-Component One-Pot Reactions for the Convenient Synthesis of Spiro [Indoline-3, 4′-Pyrano [2, 3-C] Pyrazole] Derivatives.” Tetrahedron 2 (2014): 484–89.
   Google Scholar
• Pal, S., M. N. Khan, S. Karamthulla, S. J. Abbas, and L. H. Choudhury. “One Pot Four-Component Reaction for the Efficient Synthesis of Spiro [Indoline-3, 4′-Pyrano [2, 3-C] Pyrazole]-3′-Carboxylate Derivatives.” Tetrahedron Lett. 40 (2013): 5434–40.
   Google Scholar
• Zhu, S. L., S. J. Ji, and Y. Zhang. “A Simple and Clean Procedure for Three-Component Synthesis of Spirooxindoles in Aqueous Medium.” Tetrahedron 38 (2007): 9365–72.
   Google Scholar
• GAO, S., 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 38 (2008): 9143–49.
   Google Scholar
• Zou, Y., Y. Hu, H. Liu, and D. Shi. “Rapid and Efficient Ultrasound-Assisted Method for the Combinatorial Synthesis of Spiro [Indoline-3, 4′-Pyrano [2, 3-c] Pyrazole] Derivatives.” ACS Comb. Sci. 1 (2011): 38–43.
   Google Scholar
• Ahadi, S., Z. Yasaei, and A. Bazgir. “A Clean and One-pot Synthesis of Spiroindoline-Pyranopyrazoles.” J. Heterocyclic Chem. 47 (2010): 1090–94.
   Web of Science ®Google Scholar
• Guo, R. Y., Z. M. An, L. P. Mo, S. T. Yang, S. X. Wang, and Z. H. Zhang. “Meglumine Promoted One-Pot, Four-Component Synthesis of Pyranopyrazole Derivatives.” Tetrahedron 47 (2013): 9931–38.
   Google Scholar