Piperazine-Grafted Magnetic Reduced Graphene Oxide (Fe₃O₄@rGO-NH) as a Reusable Heterogeneous Catalyst for Gewald Three-Component Reaction

References

• Khurshed Bozorov, Li Fei Nie, Jiangyu Zhao, and Haji A. Aisa, “2-Aminothiophene Scaffolds: Diverse Biological and Pharmacological Attributes in Medicinal Chemistry,” European Journal of Medicinal Chemistry 140, (2017): 465–93.
   PubMed Web of Science ®Google Scholar
• Khurshed Bozorov, Hai-Rong Ma, Jiang-Yu Zhao, Hai-Qing Zhao, Hua Chen, Khayrulla Bobakulov, Xue-Lei Xin, Burkhon Elmuradov, Khusnutdin Shakhidoyatov, and Haji A. Aisa, “Discovery of Diethyl 2, 5-Diaminothiophene-3, 4-Dicarboxylate Derivatives as Potent Anticancer and Antimicrobial Agents and Screening of anti-Diabetic Activity: Synthesis and in Vitro Biological Evaluation, Part 1,” European Journal of Medicinal Chemistry 84, (2014): 739–45.
   PubMed Web of Science ®Google Scholar
• Zita Puterová, Alžbeta Krutošíková, and Daniel Végh, “Gewald Reaction: synthesis, Properties and Applications of Substituted 2-Aminothiophenes,”Arkivoc 1, no. 209 (2010): 209–46.
   Google Scholar
• Zita Puterová, Alžbeta Krutošíková, and Daniel Végh, “Applications Substituted 2-Aminothiophenes in Drug Design,” Nova Biotechnologica 9, (2009): 167–73.
   Google Scholar
• Yijun Huang, and Alexander Dömling, “The Gewald Multicomponent Reaction,”Molecular Diversity 15, no. 1 (2011): 3–33.
   PubMed Web of Science ®Google Scholar
• Ming Shien Yen, and Jing Wang, “Synthesis and Absorption Spectra of Hetarylazo Dyes Derived from Coupler 4-Aryl-3-Cyano-2-Aminothiophenes,” Dyes and Pigments 61, no. 3 (2004): 243–50.
   Web of Science ®Google Scholar
• Chengde Wu, E. Radford Decker, Natalie Blok, Huong Bui, Tony J. You, Junmei Wang, Andree R. Bourgoyne, Vippra Knowles, Kurt L. Berens, George W. Holland, et al. “Discovery, Modeling, and Human Pharmacokinetics of N-(2-Acetyl-4, 6-Dimethylphenyl)-3-(3, 4-Dimethylisoxazol-5-Ylsulfamoyl) Thiophene-2-Carboxamide (TBC3711), a Second Generation, ETA Selective, and Orally Bioavailable Endothelin Antagonist,” Journal of Medicinal Chemistry 47, no. 8 (2004): 1969–86.
   PubMed Web of Science ®Google Scholar
• Kim Doré, Sébastien Dubus, Hoang-Anh Ho, Isabelle Lévesque, Maryse Brunette, Geneviève Corbeil, Maurice Boissinot, Guy Boivin, Michel G. Bergeron, Denis Boudreau, et al. “Fluorescent Polymeric Transducer for the Rapid, Simple, and Specific Detection of Nucleic Acids at the Zeptomole Level,” Journal of the American Chemical Society 126, no. 13 (2004): 4240–4.
   PubMed Web of Science ®Google Scholar
• Constance Rost, Siegfried Karg, Walter Riess, Maria Antonietta Loi, Mauro Murgia, and Michele Muccini, “Ambipolar Light-Emitting Organic Field-Effect Transistor,” Applied Physics Letters 85, no. 9 (2004): 1613–5.
   Web of Science ®Google Scholar
• Hsiao‐hua. Yu, Anthony E. Pullen, Michael G. Büschel, and Timothy M. Swager, “Charge‐Specific Interactions in Segmented Conducting Polymers: An Approach to Selective Ionoresistive Responses,” Angewandte Chemie International Edition 43, no. 28 (2004): 3700–3.
   PubMed Web of Science ®Google Scholar
• Dennis M. Vriezema, Johan Hoogboom, Kelly Velonia, Ken Takazawa, Peter C. M. Christianen, Jan C. Maan, Alan E. Rowan, and Roeland J. M. Nolte, “Vesicles and Polymerized Vesicles from Thiophene‐Containing Rod–Coil Block Copolymers,” Angewandte Chemie International Edition 42, no. 7 (2003): 772–6.
   PubMed Web of Science ®Google Scholar
• Karl Gewald, “Zur Reaktion Von α‐Oxo‐Mercaptanen Mit Nitrilen,” Angewandte Chemie 73, no. 3 (1961): 114.
   Google Scholar
• Madabhushi Sridhar, Rayankula Mallikarjuna Rao, Nanduri H. K. Baba, and Ravindra M. Kumbhare, “Microwave Accelerated Gewald Reaction: synthesis of 2-Aminothiophenes,” Tetrahedron Letters 48, no. 18 (2007): 3171–72.
   Web of Science ®Google Scholar
• Bruno F. Machado, and Philippe Serp, “Graphene-Based Materials for Catalysis,” Catalysis Science & Technology 2, no. 1 (2012): 54–75.
   Web of Science ®Google Scholar
• Bhaskar Garg, Tanuja Bisht, and Yong-Chien Ling, “Graphene-Based Nanomaterials: Versatile Catalysts for Carbon-Carbon Bond Forming Reactions,” Current Organic Chemistry 20, no. 15 (2016): 1547–66.
   Web of Science ®Google Scholar
• Bhaskar Garg, Tanuja Bisht, and Yong-Chien Ling, “Graphene-Based Nanomaterials as Heterogeneous Acid Catalysts: A Comprehensive Perspective,” Molecules 19, no. 9 (2014): 14582–614. no.
   PubMed Web of Science ®Google Scholar
• Bhaskar Garg, and Yong-Chien Ling, “Versatilities of Graphene-Based Catalysts in Organic Transformations,” Green Materials 1, no. 1 (2013): 47–61.
   Web of Science ®Google Scholar
• Goki Eda, and Manish Chhowalla, “Chemically Derived Graphene Oxide: Towards Large‐Area Thin‐Film Electronics and Optoelectronics,” Advanced Materials 22, no. 22 (2010): 2392–415.
   PubMed Web of Science ®Google Scholar
• Eduardo Rodrigo, Beatriz García Alcubilla, Raquel Sainz, J. L. García Fierro, Rafael Ferritto, and M. Belen Cid, “Reduced Graphene Oxide Supported Piperazine in Aminocatalysis,” Chemical Communications 50, no. 47 (2014): 6270–73.
   PubMed Web of Science ®Google Scholar
• Yongjun Gao, Ding Ma, Chunlei Wang, Jing Guan, and Xinhe Bao, “Reduced Graphene Oxide as a Catalyst for Hydrogenation of Nitrobenzene at Room Temperature,” Chemical Communications 47, no. 8 (2011): 2432–34.
   PubMed Web of Science ®Google Scholar
• Murugan Karthik, and Palaniswamy Suresh, “Greener Synthesis of Reduced Graphene Oxide‐Nickel Nanocomposite: Rapid and Sustainable Catalyst for the Reduction of Nitroaromatics,” Chemistry Select 2, no. 23 (2017): 6916–28.
   Google Scholar
• Reza Tayebee, S. Javad Ahmadi, Esmaeil Rezaei-Seresht, Farzad Javadi, Mohammad A. Yasemi, Morteza Hosseinpour, and Behrouz Maleki, “Commercial Zinc Oxide: A Facile, Efficient, and Eco-Friendly Catalyst for the One-Pot Three-Component Synthesis of Multisubstituted 2-Aminothiophenes via the Gewald Reaction,” Industrial & Engineering Chemistry Research 51, no. 44 (2012): 14577–582.
   Web of Science ®Google Scholar
• Esmail Rezaei-Seresht, Reza Tayebee, and Mohammad Yasemi, “KG-60-Piperazine as a New Heterogeneous Catalyst for Gewald Three-Component Reaction,” Synthetic Communications 43, no. 13 (2013): 1859–64.
   Web of Science ®Google Scholar
• Jeffrey Pyun, “Graphene Oxide as Catalyst: Application of Carbon Materials beyond Nanotechnology,” Angewandte Chemie International Edition 50, no. 1 (2011): 46–48.
   PubMed Web of Science ®Google Scholar
• Daniel R. Dreyer, Hong‐Peng Jia, and Christopher W. Bielawski, “Graphene Oxide: A Convenient Carbocatalyst for Facilitating Oxidation and Hydration Reactions,” Angewandte Chemie International Edition 49, no. 38 (2010): 6686–16.
   Web of Science ®Google Scholar
• Zhi Yang, Zhen Yao, Guifa Li, Guoyong Fang, Huagui Nie, Zheng Liu, Xuemei Zhou, Xi’an Chen, and Shaoming Huang, “Sulfur-Doped Graphene as an Efficient Metal-Free Cathode Catalyst for Oxygen Reduction,” ACS Nano 6, no. 1 (2012): 205–11.
   PubMed Web of Science ®Google Scholar
• Sheng Guo, Gaoke Zhang, Yadan Guo, and C. Yu Jimmy, “Graphene Oxide–Fe2O3 Hybrid Material as Highly Efficient Heterogeneous Catalyst for Degradation of Organic Contaminants,” Carbon 60, (2013): 437–44.
   Web of Science ®Google Scholar
• John Mondal, Kim Truc Nguyen, Avijit Jana, Karina Kurniawan, Parijat Borah, Yanli Zhao, and Asim Bhaumik, “Efficient Alkene Hydrogenation over a Magnetically Recoverable and Recyclable Fe3O4@GO Nanocatalyst Using Hydrazine Hydrate as the Hydrogen Source,” Chemical Communications 50, no. 81 (2014): 12095–97.
   PubMed Web of Science ®Google Scholar
• M. S. Manhas, V. V. Rao, P. A. Seetharaman, D. Succardi, and J. Pazdera, “Synthesis of Thieno-and Furo-Pyrimidinethiones,” Journal of the Chemical Society C: Organic 14, (1969) : 1937–39.
   Google Scholar
• Karl Gewald, Elfriede Schinke, and Horst Böttcher, “Heterocyclen Aus CH‐Aciden Nitrilen, VIII. 2‐Amino‐Thiophene Aus Methylenaktiven Nitrilen, Carbonylverbindungen Und Schwefel,” Chemische Berichte 99, no. 1 (1966): 94–100.
   Google Scholar
• Ali Nakhi, Raju Adepu, D. Rambabu, Ravada Kishore, G. R. Vanaja, Arunasree M. Kalle, and Manojit Pal, “Thieno [3, 2-c] Pyran-4-One Based Novel Small Molecules: Their Synthesis, Crystal Structure Analysis and in Vitro Evaluation as Potential Anticancer Agents,” Bioorganic & Medicinal Chemistry Letters 22, no. 13 (2012): 4418–4427.
   PubMed Web of Science ®Google Scholar