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Research Articles

Reusable Fe3O4/ZnO/MWCNTs Magnetic Nanocomposites Promoted Synthesis of New Naphthyridines

ORCID Icon, , , &
Pages 2927-2946 | Received 19 Aug 2020, Accepted 06 Nov 2020, Published online: 01 Dec 2020

References

  • J. Song, and B. Han, “Green Chemistry: A Tool for the Sustainable Development of the Chemical Industry,” National Science Review 2, no. 3 (2015): 255–6.
  • D. W. Morrison, D. C. Forbes, and J. Davis, “Base-Promoted Reactions in Ionic Liquid Solvents. The Knoevenagel and Robinson Annulation Reactions,” Tetrahedron Letters 42, no. 35 (2001): 6053–5.
  • Y. Zhou, J. H. Schattka, and M. Antonietti, “Room-Temperature Ionic Liquids as Template to Monolithic Mesoporous Silica with Wormlike Pores via a Sol − Gel Nanocasting Technique,” Nano Letters 4, no. 3 (2004): 477–81.
  • M. Sabbaghan, and B. Mirzaei Behbahani, “Synthesis and Optical Properties of CuO Nanostructures in Imidazolium-Based Ionic Liquids,” Materials Letters 117, no. 15 (2014): 28–30.
  • M. Sabbaghan, and P. Sofalgar, “Single-Phase γ-Fe2O3 Nanoparticles Synthesized by Green Ionothermal Method and Their Magnetic Characterization,” Ceramics International 42, no. 15 (2016): 16813–6.
  • A. Bagheri, M. Sabbaghan, and Z. Mirgani, “A Comparative Study on Properties of Synthesized MgO with Different Templates,” Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy 137 (2015): 1286–91.
  • R. Sahay, J. Sundaramurthy, P. Suresh Kumar, V. Thavasi, S. G. Mhaisalkar, and S. Ramakrishna, “Synthesis and Characterization of CuO Nanofibers, and Investigation for Its Suitability as Blocking Layer in ZnO NPs Based Dye Sensitized Solar Cell and as Photocatalyst in Organic Dye Degradation,” Journal of Solid State Chemistry 186, (2012): 261–7.
  • A. B. Djurišić, X. Chen, Y. H. Leung, and A. Man, “ZnO Nanostructures: growth, Properties and Applications,” Journal of Materials Chemistry 22, no. 14 (2012): 6526–35.
  • B. T. Zhang, X. Zheng, H. F. Li, and J. M. Lin, “Application of Carbon-Based Nanomaterials in Sample Preparation: A Review,” Analytica Chimica Acta 784 (2013): 1–17.
  • T. Xin, M. Ma, H. Zhang, J. Gu, S. Wang, M. Liu, and Q. Zhang, “A Facile Approach for the Synthesis of Magnetic Separable Fe3O4@ TiO2, Core–Shell Nanocomposites as Highly Recyclable Photocatalysts,” Applied Surface Science. 288 (2014): 51–9.
  • J. Jing, J. Li, J. Feng, W. Li, and W. W. Yu, “Photodegradation of Quinoline in Water over Magnetically Separable Fe3O4/TiO2 Composite Photocatalysts,” Chemical Engineering Journal and the Biochemical Engineering Journal 219 (2013): 355–60.
  • K. Mandel, F. Hutter, C. Gellermann, and G. Sextl, “Modified Superparamagnetic Nanocomposite Microparticles for Highly Selective HgII or CuII Separation and Recovery from Aqueous Solutions,” Separation and Purification Technology 109 (2013): 144–7.
  • A. Domling, “Recent Developments in Isocyanide Based Multicomponent Reactions in Applied Chemistry,” Chemical Reviews 106 (2006): 17–89.
  • L. F. Tietze and N. N. Rackelmann, “Domino Reactions in the Synthesis of Heterocyclic Natural Products and Analogs,” Pure and Applied Chemistry 11 (2004): 1967–83.
  • A. Domling, and I. Ugi, “Multicomponent Reactions with Isocyanides,” Angewandte Chemie 39, no. 18 (2000): 3168–210.
  • J. Kolb, B. Beck, M. Almstetter, S. Heck, E. Herdtweck, and A. Domling, “New MCRs: The First 4-Component Reaction Leading to 2,4-Disubstituted Thiazoles,” Molecular Diversity 6, no. 3–4 (2003): 297–313.
  • A. Domling, I. Ugi, and B. Werner, “The Chemistry of Isocyanides, Their Multicomponent Reactions and Their Libraries,” Molecules 8, no. 1 (2003): 53–66.
  • R. S. Bon, B. V. Vliet, N. E. Sprenkels, R. F. Schmitz, F. J. J. Kanter, C. V. Stevens, M. Swart, F. M. Bickelhaupt, M. B. Groen, and R. V. Orru, “Multicomponent Synthesis of 2-Imidazolines,” The Journal of Organic Chemistry 70, no. 9 (2005): 3542–53.
  • Luca Banfi, Andrea Basso, Giuseppe Guanti, Nicola Kielland, Claudio Repetto, and Renata Riva, “Ugi Multicomponent Reaction Followed by an Intramolecular Nucleophilic Substitution:  Convergent Multicomponent Synthesis of 1-Sulfonyl 1,4-Diazepan-5-Ones and of Their Benzo-Fused Derivatives,” The Journal of Organic Chemistry 72, no. 6 (2007): 2151–60.
  • C. V. Galliford, and K. A. Scheidt, “Catalytic Multicomponent Reactions for the Synthesis of N-Aryl Trisubstituted Pyrroles,” The Journal of Organic Chemistry 72, no. 5 (2007): 1811–3.
  • T. Erdmenger, C. Guerrero-Sanchez, J. Vitz, R. Hoogenboom, and U. S. Schubert, “Recent Developments in the Utilization of Green Solvents in Polymer Chemistry,” Chemical Society Reviews 39, no. 8 (2010): 3317–33.
  • H. Plieninger, and D. Wild, “Benzazepin-Derivate Aus 2-Äthoxy-Indol,”Chemische Berichte 99, no. 10 (1966): 3070–5.
  • T. Sakan, S. Matsubara, H. Takagi, Y. Tokunaga, and T. Miwa, “The Reactions of 2-(2-Indolyl)Ethyl Tosylates with Bases, a Novel Ring Enlargement Reaction of Indole Ring,” Tetrahedron Letters 9, no. 47 (1968): 4925–8.
  • G. Schroeter, A. Gluschke, S. Götzky, J. Huang, G. Irmisch, E. Laves, O. Schrader, and G. Stier, “Oxim-Umlagerungen in Der Tetralon-Reihe,” Berichte Der Deutschen Chemischen Gesellschaft (A and B Series) 63, no. 6 (1930): 1308–29.
  • (a) L. H. Briggs and G. C. De Ath, “A Synthesis of Dihydrocarbostyril and Homodihydrocarbostyril by Ring Enlargement and a Synthesis of Tetrahydroquinoline.” Journal of Chemical Society 1937 (1937): 456–7; (b) R. W. Richard and R. M. Smith,“The Synthesis of 1H, 2H, 5H-Azepine-2,5-Diones by Schmidt Rearrangement or Quinines. Tetrahedron Letters 7 (1966): 2361–5; (c) K. I. Booker-Milburn, I. R. Dunkin, F. C. Kelly, A. I. Khalaf, D. A. Learmonth, G. R. Proctor, and D. I. C. Scopes, Journal of Chemical Society: Perkin Transactions 1 (1997): 3261–3273.
  • (a) A. Cromarty and G. R. Proctor,“A New Azepine and Azepinone Synthesis,” Journal of Chemical Society: Chemical Communication (1968): 842–843; (b) A. Cromarty, K. E. Hque, and G. R. Proctor, Azabenzocycloheptenones: Part XIII. Ring Expansion of 1,2-Dihydroquinoline Derivatives. Journal of Chemical Society (1971): 3536–40.
  • Y. Sato, H. Kojima, and H. Shirai, “Ring Expansion Reaction of 1,2-Dihydroquinolines to 1-Benzazepines,” The Journal of Organic Chemistry 41, no. 2 (1976): 195–200.
  • Maryiam Qadir, Rachael E. Priestley, Thomas W. D. F. Rising, Thomas Gelbrich, Simon J. Coles, Michael B. Hursthouse, Peter W. Sheldrake, Neil Whittall, and K. K. (Mimi) Hii, “Synthesis of 2-Substituted 1-Benzyl-2,3,4,5-Tetrahydro-1-Benzazepines by Palladium Catalysis. Observation of a Competitive β-Hydride Elimination Pathway,” Tetrahedron Letters. 44, no. 18 (2003): 3675–8.
  • G. Dyker and H. Markwitz, “A Palladium-Catalyzed Domino Process to 1-Benzazepines,” Synthesis 1998, no. 12 (1998): 1750–4.
  • U. Martinez-Estibalez, N. Sotomayor, and E. Lete, “Pd-Catalyzed Arylation/Ring-Closing Metathesis Approach to Azabicycles,” Tetrahedron Letters. 48, no. 16 (2007): 2919–22.
  • (a) A. Suzuki and H. C. Brown, In Organic Synthesis via Boranes, vol. 3 (Milwaukee, USA: Aldrich Chemical Company, Inc.:, 2003; for selected reviews on SM crosscoupling; (b) N. Miyaura and A.Suzuki, “Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds,” Chemical Reviews 95 (1995): 2457–2483; (c) S. Kotha, K. Lahiri, and D. Kashinath,“Recent Applications of the Suzuki–Miyaura Cross-coupling Reaction in Organic Synthesis,” Tetrahedron 58 (2002): 9633–9695; (d) M. Moreno-Manas, R. Pleixats, R. M. Sebastian, A. Vallribera, and A. Roglans,“Organometallic Chemistry of 15-Membered Tri-olefinic Macrocycles: Catalysis by Palladium(0) Complexes in Carbon–Carbon Bond-Forming Reactions,” Journal of Organometallic Chemistry 689 (2004): 3669–84; (e) K. C. Nicolaou, P. G. Bulger, and D. Sarlah, “Palladiumkatalysierte Kreuzkupplungen in der Totalsynthese,” Angewandte Chemie 117 (2005): 4516–4563; (f) S. Kotha and K. Lahiri, “Expanding the Diversity of Polycyclic Aromatics Through a Suzuki–Miyaura Cross‐Coupling Strategy,” European Journal of Organic Chemistry (2007): 1221–1236; (g) S. Kotha, K. Chakraborty, and E. Brahmachary,“Improved Synthesis of the High-Mobility Organic Semiconductor Dithio­phene-Tetrathiafulvalene,” Synlett (1999): 1621–1623.
  • (a) E. J. Trybulski, E. Reeder, J. F. Blount, A. Walser, and R. I. Fryer, “2-Benzazepines. I. Synthesis of 2-Benzazepin-4-ones and -5-ones via 2-acetylenic benzophenones,” The Journal of Organic Chemistry 47, no. 12 (1982): 2441–2447; (b) P. Jenny-Lee, R. Pathak, C. B. De Koning, and W. A. L. Van Otterlo, “Synthesis of Substituted 2,3‐Dihydro‐1H‐2‐benzazepines and 1,2‐Dihydroisoquinolines Using an Isomerization‐Ring‐Closing Metathesis Strategy: Scope and Limitations,” European Journal of Organic Chemistry (2007): 4953–4961.
  • S. Kasparek, “1-, 2-, and 3-Benzazepines,” Advances in Heterocyclic Chemistry 17 (1974): 45–98.
  • Gschwend, H. U.S. Patent 3,947,585, Mar 30 (1976).
  • Tomcufcik, A. S.; Meyer, W. E.; Marsico, J. W. Eur. Pat. Appl. EP 446604, 1991; US Appl. 494387, 1990; [Chem. Abstr. 1992, 116, 235628p].
  • Saupe, T. Schaefer, P. Meyer, N. Wuerzer, B. Westphalen, and K. O. Ger, Offen. DE 3907937 (1990) [Chem. Abstr. 1991, 114, 81808s].
  • C. Cotrel, C. Guyon, G. Roussel, and G. Taurand, /10619 Eur. Pat. Appl. EP 208621 (1987) FR Appl. 85, 1985; [Chem. Abstr. 1987, 107, 39780g].
  • M. Janot, J. Guilhem, O. Contz, G. Venera, and E. Clonga, “Biomedically Relevant Chemical Constituents of Valeriana Officinalis,” Annales Pharmaceutiques Francaises 37 (1979): 413–20.
  • P. G. Waterman, and I. Muhammad, “Sesquiterpenes and Alkaloids from Cleistopholis Patens,” Phytochemistry 24, no. 3 (1985): 523–7.
  • T. F. Molinski, “Marine Pyridoacridine Alkaloids: structure, Synthesis, and Biological Chemistry,” Chemical Reviews 93, no. 5 (1993): 1825–38.
  • (a) B. Halliwell, “Antioxidant Defence Mechanisms: From the Beginning to the End (of the Beginning).” Free Radical Research 4, no. 31 (1999): 261–272; (b) F. Ahmadi, M. Kadivar, and M. Shahedi, “ Antioxidant Activity of Kelussia odoratissima Mozaff. in Model and Food Systems.” Food Chemistry 105 (2007): 57–64.
  • Mark A. Babizhayev, Anatoly I. Deyev, Valentina N. Yermakova, Igor V. Brikman, and Johan Bours, “Lipid Peroxidation and Cataracts: N-Acetylcarnosine as a Therapeutic Tool to Manage Age-Related Cataracts in Human and in Canine Eyes,” Drugs in R&D 5, no. 3 (2004): 125–39.
  • L. Liu, and M. Meydani, “Combined Vitamin C and E Supplementation Retards Early Progression of Arteriosclerosis in Heart Transplant Patients,” Nutritional Review, 60 (2002): 368–71.
  • E. Ezzatzadeh, and Z. S. Hossaini, “Green Synthesis and Antioxidant Activity of Novel Series of Benzofurans from Euparin Extracted of Petasites Hybridus,” Natural Product Research 33, no. 11 (2019): 1617.
  • E. Ezzatzadeh, and Z. S. Hossaini, “A Novel One-Pot Three-Component Synthesis of Benzofuran Derivatives via Strecker Reaction: Study of Antioxidant Activity,” Natural Product Research 34 (2018): 1–7.
  • E. Ezzatzadeh, and Z. S. Hossaini, “Four-Component Green Synthesis of Benzochromene Derivatives Using nano-KF/Clinoptilolite as Basic Catalyst: Study of Antioxidant Activity,” Molecular Diversity 24, no. 1 (2020): 81–91.
  • M. Rajabi, Z. S. Hossaini, M. A. Khalilzadeh, Sh Datta, M. Halder, and Sh A. Mousa, “Synthesis of a New Class of Furo[3,2-c]Coumarins and its Anticancer Activity,” Journal of Photochemistry and Photobiology. B, Biology 148, (2015): 66–72.
  • (a) I. Yavari, M. Sabbaghan, and Z. S. Hossaini, “Efficient Synthesis of Functionalized 2,5-Dihydrofurans and 1,5-Dihydro-2H-Pyrrol-2-Ones by Reaction of Isocyanides with Activated Acetylenes in the Presence of Hexachloroacetone.” Monatshefte für Chemie – Chemical Monthly 6, no. 139 (2008): 625–8; (b) I. Yavari, M. Sabbaghan, and Z. S. Hossaini, “ Proline-Promoted Efficient Synthesis of 4-Aryl-3,4-Dihydro-2H,5H-Pyrano[3,2-c]chromene-2,5-Diones in Aqueous Media,” Synlett 2008 (2008): 1153–4; (c) I. Yavari, Z. S. Hossaini, M. Sabbaghan, and M. Ghazanfarpour-Darjani, “Efficient Synthesis of Functionalized Spiro-2,5-Dihydro-1,2-λ5-Oxaphospholes,” Tetrahedron 63 (2007): 9423–8; (d) I. Yavari, M. Sabbaghan, Z. S. Hossaini, M. Ghazanfarpour-Darjani, “Surprising Formation of Chlorinated Butenolides from Dialkyl Acetylenedicarboxylates and Hexachloro­Acetone in the Presence of Triphenyl Phosphite,” Helvetica Chimica Acta 91 (2008): 1144–7.
  • F. Rostami-Charati and Z. S. Hossaini, “Facile Synthesis of Phosphonates via Catalyst-Free Multicomponent Reactions in Water,” Synlett 23 no. 16 (2012): 2397–2399.
  • (a) Z. S. Hossaini, D. Zareyee, F. Sheikholeslami-Farahani, S. Vaseghi, and A. Zamani, “ZnO-NR as the Efficient Catalyst for the Synthesis of New Thiazole and Cyclopentadienone Phosphonate Derivatives in Water,” Heteroatom Chemistry 28 (2017): e21362; (b) F. Rostami-charati, Z. S. Hossaini, D. Zareyee, S. Afrashteh, and M. Hosseinzadeh, “ZnO‐Nanorods as an Efficient Catalyst for the Synthesis of 1,3‐Thiazolidine Derivatives by Aqueous Multicomponent Reactions of Isothiocyanates,” Journal of Heterocyclic Chemistry 54 (2017): 1937–42; (c) F. Rostami‐Charati, Z. S. Hossaini, M. A. Khalilzadeh, and H. Jafaryan, “Solvent‐Free Synthesis of Pyrrole Derivatives,” Journal of Heterocyclic Chemistry 49 (2012): 217–20.
  • (a) F. Rostami-Charati, Z. S. Hossaini, R. Rostamian, A. Zamani, and M. Abdoli, “Green Synthesis of Indol-2-One Derivatives from N-Alkylisatins in the Presence of KF/Clinoptilolite Nanoparticles,” Chemistry of Heterocyclic Compounds 4, no. 53 (2017): 480–3; (b) I. Yavari, S. Seyfi, Z. S. Hossaini, M. Sabbaghan, and F. Shirgahi-Talari, “Efficient Synthesis of 2-Thioxo-1,3-Thiazolanes from Primary Amines, CS2, and Ethyl Bromopyruvate,” Monatshefte für Chemie-Chemical Monthly 139 (2008): 1479–82.
  • (a) S. Rezayati, F. Sheikholeslami-Farahani, Z. S. Hossaini, R. Hajinasiri, and S. Afshari Sharif Abad, “Regioselctive Thiocyanation of Aromatic and Heteroaromatic Compounds Using a Novel Bronsted Acidic Ionic Liquid,” Combinatorial Chemistry and High Throughput Screening 9 (2016): 720–7; (b) F. Tavakolinia, T. Baghipour, Z. S. Hossaini, D. Zareyee, and M. A. Khalilzadeh, “Antiproliferative Activity of Novel Thiopyran Analogs on MCF-7 Breast and HCT-15 Colon Cancer Cells: Synthesis, Cytotoxicity, Cell Cycle Analysis, and DNA-Binding,” Nucleic Acid Therapeutics, 22 (2012): 265–70.
  • (a) F. Rostami-Charati, Z. S. Hossaini, F. Sheikholeslami-Farahani, Z. Azizi, and S. A. Siadati,“Synthesis of 9H-furo [2,3-f]Chromene Derivatives by Promoting ZnO Nanoparticles,” Combinatorial Chemistry and High Throughput Screening, 18 (2015): 872–880; (b) S. S. Asadi-Ojaee, A. Mirabi, A. Shokuhi Rad, Sh. Movaghgharnezhad, and S. Hallajian,“Removal of Bismuth (III) Ions from Water Solution Using a Cellulose-Based Nanocomposite: A Detailed Study by DFT and Experimental Insights,” Journal of Molecular and Liquid Chromatography, 295 (2019): 111723; (c) A. Shokuhi Rad, V. Samipour, Sh. Movaghgharnezhad, A. Mirabi, M. H. Shahavie, and B. Kamyab Moghadasf, “X12N12 (XAl, B) Clusters for Protection of Vitamin C; Molecular Modeling Investigation,” Surfaces and Interfaces 15 (2019): 30–7; (d) Sh. Movaghgharnezhad and A. Mirabi, “Advanced Nanostructure Amplified Strategy for Voltammetric Determination of Folic Acid,” International Journal of Electrochemical Sciences 14 (2019): 10956–61.
  • H. Sajjadi-Ghotbabadi, Sh Javanshir, and F. Rostami-Charati, “Nano KF/Clinoptilolite: An Effective Heterogeneous Base Nanocatalyst for Synthesis of Substituted Quinolines in Water,” Catalysis Letters 146, no. 2 (2016): 338–44.
  • a) I. Yavari, M. Ghazanfarpour-Darjani, Z. S. Hossaini, M. Sabbaghan, and N. Hosseini, “Methoxide Ion Promoted Efficient Synthesis of 1,3-Oxathiolane-2-Thiones by Reaction of Oxiranes and Carbon Disulfide,” Molecular Diversity, 4, no. 13 (2009): 439–891; b) I. Yavari, Z. S. Hossaini, S. Souri, and S. Seyfi, “Diastereoselective Synthesis of Fused [1, 3] Thiazolo [1, 3] Oxazins and [1, 3] Oxazino [2, 3-b][1, 3] Benzothiazoles,” Molecular Diversity 13 (2009): 439.
  • a) R. Hajinasiri, Z. S. Hossaini, and F. Rostami‐Charati, “Efficient Synthesis of α‐Aminophosphonates via One‐Pot Reactions of Aldehydes, Amines, and Phosphates in Ionic Liquid,” Heteroatom Chemistry 22 (2011): 625–629; b) Rostami Charati, F.; Hossaini, Z. S.; Hosseini-Tabatabaei, M. R, “A Simple Synthesis of Oxaphospholes,” Phosphorus, Sulfur, and Silicon and the Related Elements 186 (2011): 1443–8; c) S. H. Adyani, E. Soleimani, and Z. S. Hossaini, “Silver and Copper–Magnetite Nanocomposites as Green and Magnetic Recoverable Catalysts for the Preparation of Cyclopentadiene Derivatives from a Tri-Component Condensation,” Reaction Kinetics, Mechanisms and Catalysis 128 (2019): 885–901.
  • a) M. Sabbaghan and P. Sofalgar, “Single-Phase γ-Fe2O3 Nanoparticles Synthesized by Green Ionothermal Method and Their Magnetic Characterization,” Ceramic International 42, no. 15 (2016): 16813–16816; b) I. Yavari and Z. S. Hossaini, “Synthesis of Fused α-Methylene-γ-Butyrolactone Derivatives Through Pyridine-Induced Addition of Phenols to Dimethyl Acetylenedicarboxylate,” Tetrahedron Letters 47 (2006): 4465–4468.
  • S. P. Rajendran, and K. Sengodan, “Synthesis and Characterization of Zinc Oxide and Iron Oxide Nanoparticles Using Sesbania Grandiflora Leaf Extract as Reducing Agent,” Journal of Nanoscience 2017, (2017): 1–7.
  • K. Shimada, K. Fujikawa, K. Yahara, and T. Nakamura, “Antioxidative Properties of Xanthan on the Autoxidation of Soybean Oil in Cyclodextrin Emulsion,” Journal of Agricultural and Food Chemistry 40, no. 6 (1992): 945–48.
  • G. C. Yen, and P. D. Duh, “Scavenging Effect of Methanolic Extracts of Peanut Hulls on Free-Radical and Active-Oxygen Species,” Journal of Agricultural and Food Chemistry 42, no. 3 (1994): 629–32.
  • A. Yildirim, A. Mavi, and A. A. Kara, “Determination of Antioxidant and Antimicrobial Activities of Rumex Crispus L. Extracts,” Journal of Agricultural and Food Chemistry 49, no. 8 (2001): 4083–9.

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