Preparation and Characterization of p-Phenylenediamine Supported on Nanocellulose (PDA@CNC) as Novel Recyclable Nano Catalyst for Synthesis of Spiropyran Oxide Derivatives

References

• H. Shaghaleh, X. Xu, and S. Wang, “Current Progress in Production of Biopolymeric Materials Based on Cellulose, Cellulose Nanofibers, and Cellulose Derivatives,” RSC Advances 8, no. 2 (2018): 825–42.
   PubMed Web of Science ®Google Scholar
• W. Hu, S. Chen, J. Yang, Z. Li, and H. Wang, “Functionalized Bacterial Cellulose Derivatives and Nanocomposites,” Carbohydrate Polymers 101 (2014): 1043–60.
   PubMed Web of Science ®Google Scholar
• S. Acharya and A. Chaudhary, “Bioprospecting Thermophiles for Cellulase Production: A Review,” Brazilian Journal of Microbiology: [Publication of the Brazilian Society for Microbiology] 43, no. 3 (2012): 844–56.
   PubMed Web of Science ®Google Scholar
• Y. Sun and M. Mohammadnia, “Synthesis and Characterization of Pd Based on [2, 2'-Bipyridin]-4-Amine Functionalized Nano Cellulose as a Novel and Recyclable Nano Catalyst for Suzuki Reaction,” Inorganic Chemistry Communications. 118 (2020): 107993–9.
   Web of Science ®Google Scholar
• M. Kaushik and A. Moores, “Nanocelluloses as Versatile Supports for Metal Nanoparticles and Their Applications in Catalysis,” Green Chemistry 18, no. 3 (2016): 622–37.
   Web of Science ®Google Scholar
• K. D. Hendren, T. W. Baughman, P. A. Deck, and E. J. Foster, “In Situ Dispersion and Polymerization of Polyethylene Cellulose Nanocrystal‐Based Nanocomposites,” Journal of Applied Polymer Science 137, no. 13 (2020): 48500–10.
   Web of Science ®Google Scholar
• R. R. Fazleeva, G. R. Nasretdinova, Y. N. Osin, A. I. Samigullina, A. T. Gubaidullin, and V. V. Yanilkin, “An Effective Producing Method of Nanocomposites of Ag, Au, and Pd Nanoparticles with Poly (N-Vinylpyrrolidone) and Nanocellulose,” Electrocatalysis 12, no. 3 (2021): 225–13.
   Web of Science ®Google Scholar
• V. Nenajdenko, “Fluorine in Heterocyclic Chemistry,” 5-Membered Heterocycles and Macrocycles Springer 1 (2014).
   Google Scholar
• A. Khazaei, M. A. Zolfigol, F. Karimitabar, I. Nikokar, and A. R. Moosavi-Zare, “N, 2-Dibromo-6-Chloro-3, 4-Dihydro-2 H-Benzo [e][1, 2, 4] Thiadiazine-7-Sulfonamide 1, 1-Dioxide: An Efficient and Homogeneous Catalyst for One-Pot Synthesis of 4 H-Pyran, Pyranopyrazole and Pyrazolo [1, 2-b] Phthalazine Derivatives under Aqueous Media,” RSC Advances 5, no. 87 (2015): 71402–12.
   Web of Science ®Google Scholar
• A. R. Moosavi-Zare, M. A. Zolfigol, E. Noroozizadeh, R. Salehi-Moratab, and M. Zarei, “Silica-Bonded 1, 4-Diaza-Bicyclo [2.2. 2] Octane-Sulfonic Acid Chloride Catalyzed Synthesis of Spiropyran Derivatives,” Journal of Molecular Catalysis A: Chemical 420 (2016): 246–53.
   Google Scholar
• H. Liu, S. Long, K. P. Rakesh, and G. F. Zha, “Structure-Activity Relationships (SAR) of Triazine Derivatives: Promising Antimicrobial Agents,” European Journal of Medicinal Chemistry 185 (2020): 111804.
   PubMed Web of Science ®Google Scholar
• M. S. Salem, S. A. Al-Mabrook, and M. A. El-Hashash, “Design, Synthesis and Antiproliferative Activity of Novel Heterocycles from 6-Iodo-2-Phenyl-4 H-Benzo [d][1, 3] Thiazine-4-Thione,” Journal of Sulphur Chemistry 42 (2020): 251.
   Web of Science ®Google Scholar
• M. Zarei, M. A. Zolfigol, A. R. Moosavi‐Zare, E. Noroozizadeh, and S. Rostamnia, “Three‐Component Synthesis of Spiropyrans Using SBA‐15/En Bonded Phosphorous Acid [SBA‐15/Pr‐NH1‐y (CH2PO3H2) y‐Et‐NH2‐x (CH2PO3H2) x] as a New Nanoporous Heterogeneous Catalyst,” ChemistrySelect 3, no. 43 (2018): 12144–9.
   Web of Science ®Google Scholar
• A. R. Moosavi-Zare, M. A. Zolfigol, R. Salehi-Moratab, and E. Noroozizadeh, “Synthesis of Spiropyran Derivatives over 1-(Carboxymethyl) Pyridinium Iodide as Nanostructured Pyridinium Salt under Aqueous Media,” Canadian Journal of Chemistry 95, no. 2 (2017): 194–8.
   Web of Science ®Google Scholar
• A. Maleki, M. Aghaei, and T. Kari, “Facile Synthesis of 7-Aryl-Benzo [h] Tetrazolo [5, 1-b] Quinazoline-5, 6-Dione Fused Polycyclic Compounds by Using a Novel Magnetic Polyurethane Catalyst,” Polycyclic Aromatic Compounds 39, no. 3 (2019): 266–78.
   Web of Science ®Google Scholar
• A. Maleki, “An Efficient Magnetic Heterogeneous Nanocatalyst for the Synthesis of Pyrazinoporphyrazine Macrocycles,” Polycyclic Aromatic Compounds 38, no. 5 (2018): 402–9.
   Web of Science ®Google Scholar
• A. Maleki, “Green Oxidation Protocol: Selective Conversions of Alcohols and Alkenes to Aldehydes, Ketones and Epoxides by Using a New Multiwall Carbon Nanotube-Based Hybrid Nanocatalyst via Ultrasound Irradiation,” Ultrasonics Sonochemistry 40, no. Pt A (2018): 460–4.
   PubMed Web of Science ®Google Scholar
• A. Maleki, “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 Advances 4, no. 109 (2014): 64169–73.
   Web of Science ®Google Scholar
• A. Maleki, “One-Pot Multicomponent Synthesis of Diazepine Derivatives Using Terminal Alkynes in the Presence of Silica-Supported Superparamagnetic Iron Oxide Nanoparticles,” Tetrahedron Letters 54, no. 16 (2013): 2055–9.
   Web of Science ®Google Scholar
• A. Maleki, “Fe3O4/SiO2 Nanoparticles: An Efficient and Magnetically Recoverable Nanocatalyst for the One-Pot Multicomponent Synthesis of Diazepines,” Tetrahedron 68, no. 38 (2012): 7827–33.
   Web of Science ®Google Scholar
• A. Maleki and S. Azadegan, “Amine-Functionalized Silica-Supported Magnetic Nanoparticles: preparation, Characterization and Catalytic Performance in the Chromene Synthesis,” Journal of Inorganic and Organometallic Polymers and Materials 27, no. 3 (2017): 714–9.
   Web of Science ®Google Scholar
• H. R. Shaterian, J. Farbodeh, and M. Mohammadnia, “Nano-TiO2: An Eco-Friendly and Clean Reusable Heterogeneous Catalyst for Preparation of α-Aminophosphonates under Ambient and Solvent-Free Conditions,” Phosphorus Sulfur Silicon Relat Elem 188, no. 7 (2013): 850–4.
   Web of Science ®Google Scholar
• H. R. Shaterian and M. Mohammadnia, “Acidic Brønsted Ionic Liquids Catalyzed the Preparation of 1-((Benzo [d] Thiazol-2-Ylamino)(Aryl)-Methyl) Naphthalen-2-ol Derivatives 1-[(1, 3-Benzothiazol-2-Ylamino)(Aryl) Methyl]-2-Naphthol,” South African Journal of Chemistry 66 (2013): 60–3.
   Web of Science ®Google Scholar
• H. R. Shaterian and M. Mohammadnia, “Mild Preparation of 2-Amino-3-Cyano-4-Aryl-4 H-Benzo [h] Chromenes and 2-Amino-3-Cyano-1-Aryl-1 H-Benzo [f] Chromenes, under Solvent-Free Conditions, Catalyzed by Recyclable Basic Ionic Liquids,” Research on Chemical Intermediates 41, no. 3 (2015): 1301–13.
   Web of Science ®Google Scholar
• L. Danqing, J. Ming, L. Li, and M. Mohammadnia, “Preparation and Characterization of Cu Supported on 2‐(1H‐Benzo [d] Imidazol‐2‐yl) Aniline‐Functionalized Fe3O4 Nanoparticles as a Novel Magnetic Catalyst for Ullmann and Suzuki Cross‐Coupling Reactions,” Applied Organometallic Chemistry 34 (2020): e5820.
   Web of Science ®Google Scholar
• J. Chen, L. Dai, J. Li, and M. Mohammadnia, “Pd Based on 2‐Aminopyrimidine and 1H‐Benzo [d] Imidazol‐2‐Amine functionalizedFe3O4 Nanoparticles as Novel Recyclable Magnetic Nanocatalysts for Ullmann Coupling Reaction,” Applied Organometallic Chemistry 34 (2020): e5708.
   Web of Science ®Google Scholar
• D. S. Raghuvanshi and K. N. Singh, “An Efficient Protocol for Multicomponent Synthesis of Spirooxindoles Employing L‐Proline as Catalyst at Room Temperature,” Journal of Heterocyclic Chemistry 47, no. 6 (2010): 1323–7.
   Web of Science ®Google Scholar
• G. S. Hari and Y. R. Lee, “Efficient One-Pot Synthesis of Spirooxindole Derivatives by Ethylenediamine Diacetate Catalyzed Reactions in Water,” Synthesis 2010, no. 03 (2010): 453–64.
   Google Scholar
• S. J. Chai, Y. F. Lai, J. C. Xu, H. Zheng, Q. Zhu, and P. F. Zhang, “One‐Pot Synthesis of Spirooxindole Derivatives Catalyzed by Lipase in the Presence of Water,” Advanced Synthesis & Catalysis 353, no. 2–3 (2011): 371–5.
   Web of Science ®Google Scholar
• H. M. Meshram, B. R. V. Prasad, and D. A. Kumar, “A Green Approach for Efficient Synthesis of N-Substituted Pyrroles in Ionic Liquid under Microwave Irradiation,” Tetrahedron Letters 51, no. 27 (2010): 3477–80.
   Web of Science ®Google Scholar
• Y. Li, H. Chen, C. Shi, D. Shi, and S. Ji, “Efficient One-Pot Synthesis of Spirooxindole Derivatives Catalyzed by l-Proline in Aqueous Medium,” Journal of Combinatorial Chemistry 12, no. 2 (2010): 231–7.
   PubMedGoogle Scholar
• S. L. Zhu, S. J. Ji, and Y. Zhang, “A Simple and Clean Procedure for Three-Component Synthesis of Spirooxindoles in Aqueous Medium,” Tetrahedron 63, no. 38 (2007): 9365–72.
   Web of Science ®Google Scholar
• L. M. Wang, N. Jiao, J. Qiu, J. J. Yu, J. Q. Liu, F. L. Guo, and Y. Liu, “Sodium Stearate-Catalyzed Multicomponent Reactions for Efficient Synthesis of Spirooxindoles in Aqueous Micellar Media,” Tetrahedron 66, no. 1 (2010): 339–43.
   Web of Science ®Google Scholar
• B. Karmakar, A. Nayak, and J. Banerji, “A Clean and Expedient Synthesis of Spirooxindoles in Aqueous Media Catalyzed over Nanocrystalline MgO,” Tetrahedron Letters 53, no. 37 (2012): 5004–7.
   Web of Science ®Google Scholar
• A. Khalafi-Nezhad, E. S. Shahidzadeh, S. Sarikhani, and F. Panahi, “A New Silica-Supported Organocatalyst Based on L-Proline: An Efficient Heterogeneous Catalyst for One-Pot Synthesis of Spiroindolones in Water,” Journal of Molecular Catalysis A: Chemical 379 (2013): 1–8.
   Google Scholar
• G. D. Wang, X. N. Zhang, and Z. H. Zhang, “One‐Pot Three‐Component Synthesis of Spirooxindoles Catalyzed by Hexamethylenetetramine in Water,” Journal of Heterocyclic Chemistry 50, no. 1 (2013): 61–5.
   Web of Science ®Google Scholar
• L. M. Elwarrakya, M. A. Abdel-Fattaha, B. D. Garyb, G. A. Piazzab, and A. H. Abadia, “An Efficient and Green One-Pot Synthesis of Novel Spirooxindole Derivatives with Potential anti-Tumor Activity in an Aqueous Solvent,” Chemical Rapid Communications 2 (2014): 33–40.
   Google Scholar
• H. Ramadoss, D. Saravanan, S. P. N. Sudhan, and S. S. Mansoor, “Synthesis and Antimicrobial Evaluation of Diversely Substituted Spirooxindole Derivatives,” Der Pharmacia Lettre 8 (2016): 25–9.
   Google Scholar