Preparation of Magnetic Cu(II) Nano-structure (Based on Nano-Fe₃O₄) and Application to the Synthesis of Hexahydroquinoline Derivatives

References

• Arkaitz Correa, Olga García Mancheño, and Carsten Bolm, “Iron-catalysed Carbon–Heteroatom and Heteroatom–Heteroatom Bond Forming Processes,” Chemical Society Reviews 37, no. 6 (2008): 1108–17.
   PubMed Web of Science ®Google Scholar
• Alexander Domling, Wei Wang, and Kan Wang, “Chemistry and Biology of Multicomponent Reactions,” Chemical Reviews 112, (2012): 3083–135.
   PubMed Web of Science ®Google Scholar
• Benjamin Rotstein, Serge Zaretsky, Vishal Rai, and Andrei Yudin, “Small Heterocycles in Multicomponent Reactions,” Chemical Reviews 114, no. 16 (2014): 8323–59.
   PubMed Web of Science ®Google Scholar
• Jieping Zhu and Hugues Bienaymé, Multicomponent Reactions (Weinheim: Wiley-VCH, 2010), 121–68.‏
   Google Scholar
• Robert W. Armstrong, Andrew P. Combs, Paul A. Tempest, S. David Brown, and Thomas A. Keating, “Multiple-Component Condensation Strategies for Combinatorial Library Synthesis,” Accounts of Chemical Research 29, no. 3 (1996): 123–31.
   Web of Science ®Google Scholar
• Tryfon Zarganes‐ Tzitzikas, Ajay Chandgude, and Alexander Dömling, “Multicomponent Reactions, Union of MCRs and Beyond,” The Chemical Record 15 (2015): 981–96.
   PubMed Web of Science ®Google Scholar
• Ivar Ugi, Alexander Dömling, and Werner Hörl, “Multicomponent Reactions in Organic Chemistry,” Endeavour 18, no. 3 (1994): 115–22.
   Web of Science ®Google Scholar
• C. Von Mannich and W. Krösche, “Ueber Ein Kondensationsprodukt Aus Formaldehyd, ammoniak Und Antipyrin,” Archiv Der Pharmazie Banner 250 (1912): 647–67.
   Google Scholar
• Adolph Strecker, “Ueber Die Künstliche Bildung Der Milchsäure Und Einen Neuen, dem Glycocoll Homologen Körper,” European Journal of Organic Chemistry 75 (1850): 27–45.
   Google Scholar
• Jeffrey T. Kuethe, Donald R. Gauthier, Gregory L. Beutner, and Nobuyoshi Yasuda, “A Concise Synthesis of (S)-N-Ethoxycarbonyl-α-Methylvaline,” The Journal of Organic Chemistry 72, no. 19 (2007): 7469–72.
   PubMed Web of Science ®Google Scholar
• Ivar Ugi, “The, α‐Addition of Immonium Ions and Anions to Isonitriles Accompanied by Secondary Reactions,” Angewandte Chemie International Edition in English 1 (1962): 8–21.
   Google Scholar
• P. L. Pauson, and I. U. Khand, “Uses of Cobalt‐Carbonyl Acetylene Complexes in Organic Synthesis,” Annals of the New York Academy of Sciences 295, no. 1 (1977): 2–14.
   Google Scholar
• A. Hantzsch, “Condensationsprodukte Aus Aldehydammoniak Und Ketonartigen Verbindungen,” Berichte Der Deutschen Chemischen Gesellschaft 14, no. 2 (1881): 1637–8.
   Google Scholar
• Hermann Staudinger, “Zur Kenntniss Der Ketene. Diphenylketen,” Justus Liebig's Annalen Der Chemie 356, no. 1-2 (1907): 51–123.
   Google Scholar
• Najmeh Edraki, Ahmad Mehdipour, Mehdi Khoshneviszadeh, and Ramin Miri, “Dihydropyridines: Evaluation of Their Current and Future Pharmacological Applications,” Drug Discovery Today 14, no. 21-22 (2009): 1058–66.
   PubMed Web of Science ®Google Scholar
• J. L. Reid, P. A. Meredith, and F. Pasanisi, “Clinical Pharmacological Aspects of Calcium Antagonists and Their Therapeutic Role in Hypertension,” Journal of Cardiovascular Pharmacology 7 (1985): S18–S20.
   PubMed Web of Science ®Google Scholar
• Cihat Safak and Rahime Simsek, “Fused 1,4-Dihydropyridines as Potential Calcium Modulatory Compounds,” Mini-Reviews in Medicinal Chemistry 6, no. 7 (2006): 747–55.
   PubMed Web of Science ®Google Scholar
• Theophile R. Godfraind, Miller Robert, and Wibo Maurice, “Calcium Antagonism and Calcium Entry Blockade,” Pharmacological Reviews, 38 (1986): 321–416.
   PubMed Web of Science ®Google Scholar
• R. Mannhold, B. Jablonka, W. Voigt, K. Schönafinger, and E. Schraven, “Antagonism of Elnadipine Derivatives: comparative SAR,” European Journal of Medicinal Chemistry 27, no. 3 (1992): 229–35.
   Web of Science ®Google Scholar
• Shi-Jun Yü, Si Wu, Xin-Min Zhao, and Cheng-Wei Lü, “Green and Efficient Synthesis of Acridine-1,8-diones and Hexahydroquinolines via a KH2PO4 Catalyzed Hantzsch-type Reaction in Aqueous Ethanol,” Research on Chemical Intermediates 43, no. 5 (2017): 3121–30.
   Web of Science ®Google Scholar
• Elham Tabrizian and Ali Amoozadeh, “Sulfamic Acid‐Functionalized Nano‐titanium Dioxide as a Novel and Highly Efficient Heterogeneous Nanocatalyst for One‐Pot and Solvent‐Free Synthesis of Hexahydroquinolines,” Journal of the Chinese Chemical Society 64, no. 3 (2017): 331–6.
   Web of Science ®Google Scholar
• Ardeshir Khazaei, Leila Jafari‐Ghalebabakhani, Esmaeil Ghaderi, Mahsa Tavasoli, and Ahmad Reza Moosavi‐Zare, “Synthesis, characterization and Application of Nano‐CoAl2O4 as an Efficient Catalyst in the Preparation of Hexahydroquinolines,” Applied Organometallic Chemistry 31, no. 12 (2017): e3815.
   Web of Science ®Google Scholar
• Ali Amoozadeh, Salman Rahmani, Mehrnoosh Bitaraf, Fatemeh Bolghan Abadi, and Elham Tabrizian, “Nano-zirconia as an Excellent Nano Support for Immobilization of Sulfonic Acid: A New, Efficient and Highly Recyclable Heterogeneous Solid Acid Nanocatalyst for Multicomponent Reactions,” New Journal of Chemistry 40, no. 1 (2016): 770–80.
   Web of Science ®Google Scholar
• Ardeshir Khazaei, Negin Sarmasti, Jaber Yousefi Seyf, and Mahsa Tavasoli, “Synthesis of Hexahydroquinoline (HHQ) derivatives Using ZrOCl2·8H2O as a Potential Green Catalyst and Optimization of Reaction Conditions Using Design of Experiment (DOE),” RSC Advances 5, no. 123 (2015): 101268–75.
   Web of Science ®Google Scholar
• Ali Amoozadeh, Sanaz Golian, and Salman Rahmani, “TiO2-coated Magnetite Nanoparticle-Supported Sulfonic Acid as a New, Efficient, Magnetically Separable and Reusable Heterogeneous Solid Acid Catalyst for Multicomponent Reactions,” RSC Advances 5, no. 57 (2015): 45974–82.
   Web of Science ®Google Scholar
• Ahmad Reza Moosavi-Zare, Mohammad Ali Zolfigol, Mahmoud Zarei, Abdolkarim Zare, and Javad Afsar, “Design, Characterization and Application of Silica-bonded Imidazolium-sulfonic Acid Chloride as a Novel, Active and Efficient Nanostructured Catalyst in the Synthesis of Hexahydroquinolines,” Applied Catalysis A: General 505 (2015): 224–34.
   Web of Science ®Google Scholar
• Xianqiao Liu, Zhiya Ma, Jianmin Xing, and Huizhou Liu, “Preparation and Characterization of Amino–Silane Modified Superparamagnetic Silica Nanospheres,” Journal of Magnetism and Magnetic Materials 270, no. 1-2 (2004): 1–6.
   Web of Science ®Google Scholar
• Ardeshir Khazaei, Negin Sarmasti, and Jaber Yousefi Seyf, “Waste to Wealth: Conversion of Nano‐magnetic Eggshell (Fe3O4@ Eggshell) to Fe3O4@ Ca(HSO4)2: Cheap, Green and Environment‐Friendly Solid Acid Catalyst,” Applied Organometallic Chemistry 32, no. 4 (2018): e4308.
   Web of Science ®Google Scholar
• Ardeshir Khazaei, Maryam Mahmoudiani Gilan, and Negin Sarmasti, “Magnetic‐Based Picolinaldehyde–Melamine Copper Complex for the One‐Pot Synthesis of Hexahydroquinolines via Hantzsch Four‐Component Reactions,” Applied Organometallic Chemistry 32, no. 3 (2018): e4151.
   Web of Science ®Google Scholar
• Hong Xu, Naihu Tong, Longlan Cui, Ying Lu, and Hongchen Gu, “Preparation of Hydrophilic Magnetic Nanospheres with High Saturation Magnetization,” Journal of Magnetism and Magnetic Materials 311, no. 1 (2007): 125–30.
   Web of Science ®Google Scholar
• Awawou Paboudam, Christian Gérard, Aminou Mohamadou, Moise Agwara, Mariam Condenand, and Peter T. Ndifon, “Solution Studies on Co (II), Ni (II), Cu (II), and Zn (II) Complexes of Hexamethylenetetramine in Aqueous and Non-Aqueous Solvents,” International Journal of Inorganic Chemistry 2014 (2014): 9.
   Google Scholar
• Ali Haghtalab and Jaber Yousefi Seyf, “Vapor–Liquid and Solid–Liquid Modeling with a Universal Quasichemical Segment-Based Activity Coefficient Model,” Industrial & Engineering Chemistry Research 54, no. 34 (2015): 8611–23.
   Web of Science ®Google Scholar
• Daniel Frey, Fredrik Engelhardt, and Edward Greitzer, “A Role for "One-Factor-at-a-Time" Experimentation in Parameter Design,” Research in Engineering Design 14, no. 2 (2003): 65–74.
   Web of Science ®Google Scholar
• Thomas Edgar, David Mautner Himmelblau, and Leon Lasdon, Optimization of Chemical Processes, Vol. 2 (New York, NY: McGraw-Hill, 2001).‏
   Google Scholar
• Gowravaram Sabitha, G. S. Kiran Kumar Reddy, C. H. Srinivas Reddy, and J. S. Yadav, “A Novel TMSI-mediated Synthesis of Hantzsch 1, 4-Dihydropyridines at Ambient Temperature,” Tetrahedron Letters 44, no. 21 (2003): 4129–31.
   Web of Science ®Google Scholar
• Muchchintala Maheswara, Vidavalur Siddaiah, Yerra Koteswara Rao, Yew-Min Tzeng, and Chenchugari Sridhar, “A Simple and Efficient One-Pot Synthesis of 1,4-Dihydropyridines Using Heterogeneous Catalyst under Solvent-free Conditions,” Journal of Molecular Catalysis A: Chemical 260, no. 1-2 (2006): 179–80.
   Google Scholar
• Ardeshir Khazaei, Ahmad Reza Moosavi-Zare, Hadis Afshar-Hezarkhania, and Vahid Khakyzadeha, “Nano-ferrous Ferric Oxide (nano-Fe3O4): Magnetite Catalytic System for the One-Pot Four-Component Tandem Imine/Enamine Formation-Knoevenagel–Michael-Cyclocondensation Reaction of Dimedone, Aldehydes, β-ketoesters and Ammonium Acetate under Green Media,” RSC Advances 4 (2014): 32142–7.
   Web of Science ®Google Scholar
• Shao-Jun Song, Zi-Xing Shan, and Yong Jin, “One-Pot Synthesis of Hexahydroquinolines via Hantzsch Four-component Reaction Catalyzed by a Cheap Amino Alcohol,” Synthetic Communications 40, no. 20 (2010): 3067–77.
   Web of Science ®Google Scholar
• Sepideh Ehsanifar and Masoud Mokhtary, “3-Carboxy-1-Sulfopyridin-1-ium Chloride ([CPySO3H]+Cl−): An Efficient Catalyst for One-Pot Synthesis of Hexahydroquinoline-3-Carboxamides,” Heterocyclic Communications 24, no. 1 (2018): 27–9.
   Web of Science ®Google Scholar
• Tibor Pasinszki, Melinda Krebsz, Győző György Lajgut, Tünde Kocsis, László Kótai, Sushama Kauthale, Sunil Tekale, and Rajendra Pawar, “Copper Nanoparticles Grafted on Carbon Microspheres as Novel Heterogeneous Catalysts and Their Application for the Reduction of Nitrophenol and One-pot Multicomponent Synthesis of Hexahydroquinolines,” New Journal of Chemistry 42, no. 2 (2018): 1092–8.
   Web of Science ®Google Scholar
• D. Patil, D. Chandam, A. Mulik, S. Jagdale, P. Patil, and M. Deshmukh, “One Pot Four Component Sequential Synthesis of Hexahydroquinoline Derivatives in Aqueous Media via Enaminone Intermediates: A Green Protocol,” Journal of Saudi Chemical Society 21 (2017): S329–S38.
   Web of Science ®Google Scholar
• Kahdijah S. Alghamdi, Nesreen S. I. Ahmed, D. Bakhotmah, and Mohamed Mokhtar, “Chitosan Decorated Copper Nanoparticles as Efficient Catalyst for Synthesis of Novel Quinoline Derivatives”. Perprints 6 (2018): 1–17.
   Google Scholar
• Davood Azarifar, Roshanak Asadpoor, Omolbanin Badalkhani, Mehdi Jaymand, Elham Tavakoli, and Mona Bazouleh, “Sulfamic‐Acid‐Functionalized Fe3‐xTixO4 Nanoparticles as Novel Magnetic Catalyst for the Synthesis of Hexahydroquinolines under Solvent‐Free Condition,” ChemistrySelect 3, no. 48 (2018): 13722–8.
   Web of Science ®Google Scholar
• Abdolkarim Zare, Fereshteh Abi, Ahmad Reza Moosavi-Zare, Mohammad Hassan Beyzavi, and Mohammad Ali Zolfigol, “Synthesis, characterization and Application of Ionic Liquid 1,3-Disulfonic Acid Imidazolium Hydrogen Sulfate as an Efficient Catalyst for the Preparation of Hexahydroquinolines,” Journal of Molecular Liquids 178 (2013): 113–21.
   Web of Science ®Google Scholar
• Ardeshir Khazaei, Mohammad Ali Zolfigol, Ahmad Reza Moosavi, Javad Zare, Abdolkarim Afsar, Vahid Zare, Mohammad Hassan Khakyzadeh, and d Beyzavi, “Synthesis of Hexahydroquinolines Using the New Ionic Liquid Sulfonic Acid Functionalized Pyridinium Chloride as a Catalyst,” Chinese Journal of Catalysis 34, no. 10 (2013): 1936–44.
   Web of Science ®Google Scholar
• Sadegh Rostamnia, Ayat Nuri, Hongchuan Xin, Ali Pourjavadi, and Seyed Hassan Hosseini, “Water Dispersed Magnetic Nanoparticles (H2O-DMNPs) of γ-Fe2O3 for Multicomponent Coupling Reactions: a Green, Single-Pot Technique for the Synthesis of Tetrahydro-4H-Chromenes and Hexahydroquinoline Carboxylates,” Tetrahedron Letters 54, no. 26 (2013): 3344–7.
   Web of Science ®Google Scholar
• Xiao-Hui Yang, Ping-Hu Zhang, Yong-Hong Zhou, Cheng-Guo Liu, Xiao-Yu Lin, and Jing-Fang Cui, “Synthesis and Antioxidant Evaluation of Novel 4-Arylhexahydroquinolines from Lignin.” ARKIVOC. 2011, no. 10(2011): 327–37.
   Google Scholar