205
Views
5
CrossRef citations to date
0
Altmetric
Research Articles

Mortar–Pestle Grinding Technique as an Efficient and Green Method Accelerates the Tandem Knoevenagel–Michael Cyclocondensation Reaction in the Presence of Ethylenediamine Immobilized on the Magnetite Nanoparticles

ORCID Icon, , ORCID Icon &
Pages 5869-5891 | Received 22 Jun 2022, Accepted 25 Jul 2022, Published online: 18 Aug 2022

References

  • J.C. Hernández, and C. Bolm, “Altering Product Selectivity by Mechanochemistry,” The Journal of Organic Chemistry 82, no. 8 (2017): 4007–19.
  • L. Takacs, “The Historical Development of Mechanochemistry,” Chemical Society Reviews 42, no. 18 (2013): 7649–59.
  • Burçak Içli, Nicolas Christinat, Justus Tönnemann, Christian Schüttler, Rosario Scopelliti, and Kay Severin, “Synthesis of Molecular Nanostructures by Multicomponent Condensation Reactions in a Ball Mill,” Journal of the American Chemical Society 131, no. 9 (2009): 3154–5.
  • L.P. Jameson, and S.V. Dzyuba, “Expeditious, Mechanochemical Synthesis of BODIPY Dyes,” Beilstein Journal of Organic Chemistry 9 (2013): 786–90.
  • Verónica Estévez, Mercedes Villacampa, and J. Carlos Menéndez, “Three-Component Access to Pyrroles Promoted by the CAN–Silver Nitrate System under High-Speed Vibration Milling Conditions: A Generalization of the Hantzsch Pyrrole Synthesis,” Chemical Communications 49, no. 6 (2013): 591–3.
  • Y.-J. Tan, Z. Zhang, F.-J. Wang, H.-H. Wu, and Q.-H. Li, “Mechanochemical Milling Promoted Solvent-Free Imino Diels–Alder Reaction Catalyzed by FeCl3: diastereoselective Synthesis of Cis-2,4-Diphenyl-1,2,3,4-Tetrahydroquinolines,” RSC Advances 4, no. 67 (2014): 35635–8.
  • T.L. Cook, J.A. Walker, and J. Mack, “Scratching the Catalytic Surface of Mechanochemistry: A Multi-Component CuAAC Reaction Using a Copper Reaction Vial,” Green Chemistry 15, no. 3 (2013): 617–9.
  • D. Prochowicz, P. Yadav, M. Saliba, M. Saski, S.M. Zakeeruddin, J. Lewiński, and M. Grätzel, “Mechanosynthesis of Pure Phase Mixed-Cation MAxFA1 − xPbI3 Hybrid Perovskites: Photovoltaic Performance and Electrochemical Properties,” Sustainable Energy & Fuels 1, no. 4 (2017): 689–93.
  • (a) A. DöMling, “Recent Developments in Isocyanide-Based Multicomponent Reactions in Applied Chemistry,” Chemical Reviews 106, no. 1 (2006): 17–89. (b) H. Alinezhad, M. Tajbakhsh, B. Maleki, and F. Pourshaban Oushibi, “Acidic Ionic Liquid [H-NP]HSO4 Promoted One-Pot Synthesis of Dihydro-1H-Indeno[1,2-b]Pyridines and Polysubstituted Imidazoles,” Polycyclic Aromatic Compounds 40, no. (2020): 1485–1500. (c) M. Nikpassand, and L. Zare Fekri, “Catalyst-Free Synthesis of Mono and Bis Spiro Pyrazolopyridines in DSDABCO as a Novel Media,” Chemical Methodologies 4, no. 4 (2020): 437–46. (d) B. Maleki, and S. Sheikh, “Nano Polypropylenimine Dendrimer (DAB-PPI-G1): As a Novel Nano Basic-Polymer Catalyst for One-Pot Synthesis of 2-Amino-2-Chromene Derivatives,” RSC Advances 5 (2015): 42997–3005. (e) B. Maleki, H. Natheghi, R. Tayebee, H. Alinezhad, A. Amiri, S.A. Hossieni, and S.M.M. Nouri, “Synthesis and Characterization of Nanorod Magnetic Co–Fe Mixed Oxides and Its Catalytic Behavior towards One-Pot Synthesis of Polysubstituted Pyridine Derivatives,” Polycyclic Aromatic Compounds 40, no. 3 (2020): 633–43. (f) A.R. Salih, and Z.A.K. Al-Messri, “Synthesis of Pyranopyrazole and Pyranopyrimidine Derivatives Using Magnesium Oxide Nanoparticles and Evaluation as Corrosion Inhibitors for Lubricants,” Eurasian Chemical Communications 3, no. 8 (2021): 533–41. (g) H.R. Saadati-Moshtaghin, B. Maleki, R. Tayebee, S. Kahrobaei, and F. Abbasinohoji, “6-Methylguanamine-Supported CoFe2O4: An Efficient Catalyst for One-Pot Three-Component Synthesis of Isoxazol-5(4H)-One Derivatives,” Polycyclic Aromatic Compounds 42, no. 3 (2022): 885–96. (h) B. Malekia, and S. Sheikh, “One-Pot Synthesis of 2-Amino-2-Chromene and 2-Amino-3-Cyano-4H-Pyran Derivatives Promoted by Potassium Fluoride,” Organic Preparations and Procedures International 47 (2015): 368–78.
  • (a) Y.L. Gu, “Multicomponent Reactions in Unconventional Solvents: State of the Art,” Green Chemistry 14, no. 8 (2012): 2091–2128. (b) M. Rohaniyan, A. Davoodnia, and S.A. Beyramabadi, “Successful Application of a Keplerate-Type, Giant-Ball Nanoporous Isopolyoxomolybdate as a Reusable Green Catalyst for Atom-Economy Synthesis of Tetrahydrobenzo[a]Xanthene-11-Ones,” Chemical Methodologies 4 (2020): 285–96. (c) M. Rohaniyan, A. Davoodnia, A. Khojastehnezhad, and S.A. Beyramabadi, “Catalytic Evaluation of Newly Prepared GO-SB-H2PMo as an Efficient and Reusable Nanocatalyst for the Neat Synthesis of Amidoalkyl Naphthols,” Eurasian Chemical Communications 2, no. 3 (2020): 329–39. (d) N. Irannejad-Gheshlaghchaei, A. Zare, A. Banaei, H. Kaveh, and N. Varavi, “N,N,N',N'-Tetramethyl-N,N'-Bis(Sulfo)Ethane-1,2- Diaminium Mesylate as a Highly Effective and Dual-Functional Catalyst for the Synthesis of 1-Thioamidoalkyl-2-Naphthols,” Chemical Methodologies 4, no. 4 (2020): 400–07. (e) B. Baghernejad, and M. Fiuzat, “A New Strategy for the Synthesis of 2-Amino-4H-Pyran Derivatives in Aqueous Media Using DABCO-Cucl Complex as a Novel and Efficient Catalyst,” Eurasian Chemical Communications 2, no. 11 (2020): 1088–92. (f) M. Nikpassand, and L. Zare Fekri, “Catalyst-Free Synthesis of Mono and Bis Spiro Pyrazolopyridines in DSDABCO as a Novel Media,” Chemical Methodologies 4, no. 4 (2020): 437–446. (g) J. Albadi, H.A. Samimi, and A.R. Momeni, “Alumina-Supported Cobalt Nanoparticles Efficiently Catalyzed the Synthesis of Chromene Derivatives under Solvent-Free Condition,” Chemical Methodologies 4, no. 5 (2020): 565–71. (h) A.R. Moosavi-Zare, and H. Afshar-Hezarkhani, “Application of [Pyridine-1-SO3H-2-COOH]Cl as an Efficient Catalyst for the Preparation of Hexahyroquinolines,” Eurasian Chemical Communications 2, no. 4 (2020): 465–74. (i) A.R. Moosavi-Zare, M.A. Zolfigol, and Z. Rezanejad, “The Synthesis of α,α′-Bis(Arylidene)Cycloalkanones Using Sulfonic Acid Functionalized Pyridinium Chloride,” Chemical Methodologies 4, no. 5 (2020): 614–22. (j) E. Kolvari, A. Arab, and M. Robati, “Biginelli Reaction Catalyzed by Elemental Bromine as a Novel Lewis Acid Catalyst, under Mild Conditions,” Eurasian Chemical Communications 2, no. 8 (2020): 909–15. (k) F. Mohamadpour, and M. Feilizadeh, “Salicylic Acid as a Bio-Based and Natural Brønsted Acid Catalyst Promoted Green and Solvent-Free Synthesis of Various Xanthene Derivatives,” Chemical Methodologies 4, no. 5 (2020): 647–59. (l) B. Baghernejad, and M. Rostami Harzevili, “Nano-Cerium Oxide/Aluminum Oxide: An Efficient and Useful Catalyst for the Synthesis of Tetrahydro[a]Xanthenes-11-One Derivatives,” Chemical Methodologies 5, no. 2 (2021): 90–95.
  • (a) F. Kamali, and F. Shirini, “Effective and Convenient Synthesis of 2-Amino-4H-Chromenes Promoted by Melamine as a Recyclable Organocatalyst,” Zeitschrift Für Naturforschung B 68, no. 7 (2013): 818–290. (b) R. Hajinasiri, and S. Rezayati, “Solvent-Free Synthesis of 1,2-Disubstituted Derivatives of 1,2-Dihydroisoquinoline, 1,2-Dihydroquinoline and 1,2-Dihydropyridine,” Z. Naturforsch 68b (2013): 818–22. (c) B. Baghernejad, and L. Nazari, “Synthesis of Indeno [1,2-b] Pyridine Derivatives in the Precense of Nano CeO2/ZnO,” Eurasian Chemical Communications 3, no. 5 (2021): 319–326.
  • A.S.K. Hashmi, and G.L. Hutchings, “Gold Catalysis,” Angewandte Chemie (International ed. in English) 45, no. 47 (2006): 7896–936.
  • C. Burda, X.B. Chen, R.B. Narayanan, and M.A. El-Sayed, “Chemistry and Properties of Nanocrystals of Different Shapes,” Chemical Reviews 105, no. 4 (2005): 1025–102.
  • V. Sokolova, and M. Epple, “Inorganic Nanoparticles as Carriers of Nucleic Acids into Cells,” Angewandte Chemie (International ed. in English) 47, no. 8 (2008): 1382–95.
  • J.T. Hu, T.W. Odom, and C.M. Lieber, “Chemistry and Physics in One Dimension: Synthesis and Properties of Nanowires and Nanotubes,” Accounts of Chemical Research 32, no. 5 (1999): 435–45.
  • P. Macnaghten, M.B. Kearnes, and B. Wynne, “Nanotechnology, Governance, and Public Deliberation: What Role for the Social Sciences?,” Science Communication 27, no. 2 (2005): 268–91.
  • S. Kango, S. Kalia, A. Celli, J. Njuguna, Y. Habibi, and R. Kumar, “Surface Modification of Inorganic Nanoparticles for Development of Organic-Inorganic nanocomposites-A Review,” Progress in Polymer Science 38, no. 8 (2013): 1232–61.
  • (a) S. Shylesh, V. Schunemann, and W.R. Thiel, “Magnetically Separable Nanocatalysts: Bridges between Homogeneous and Heterogeneous Catalysis,” Angewandte Chemie International Edition 2 (2010): 3428–59. (b). L.P. Zhu, F. Stubbs, R. Ho, C.P. Liu, Ship, J.A. Maguire, and N.S. Hosmane, “Magnetic Nanocomposites: A New Perspective in Catalysis,” ChemCatChem 49 (2010): 365–74.
  • M.L. Verma, M. Puri, and C.J. Barrow, “Recent Trends in Nanomaterials Immobilised Enzymes for Biofuel Production,” Critical Reviews in Biotechnology 36, no. 1 (2016): 108–19.
  • (a) S. Rezayati, F. Kalantari, A. Ramazani, S. Sajjadifar, H. Aghahosseini, and A. Rezaei, “Magnetic Silica-Coated Picolylamine Copper Complex [Fe3O4@SiO2@GP/Picolylamine-Cu(II)]-Catalyzed Biginelli Annulation Reaction,” Inorganic Chemistry 61, no. 2 (2022): 992–1010.(b) F. Laffafchi, M. Tajbakhsh, Y. Sarrafi, B. Maleki, and M. Ghani, “Cu-Modified Magnetic Creatine as an Efficient Catalyst for Regioselective Preparation of 1,2,3-Triazoles Derivatives,” Polycyclic Aromatic Compounds (2022)https://doi.org/10.1080/10406638.2022.2070224; (c) H.R. Saadati-Moshtaghin, B. Maleki, R. Tayebee, S. Kahrobaei, and F. Abbasinohoji, “6-Methylguanamine-Supported CoFe2O4: An Efficient Catalyst for One-Pot Three-Component Synthesis of Isoxazol-5(4H)-One Derivatives,” Polycyclic Aromatic Compounds 42, no. 3 (2022): 885–96. [Mismatch] (d) S. Sargazi Karbasaki, Gh Bagherzade, B. Maleki, and M. Ghani, “Fabrication of Sulfamic Acid Functionalized Magnetic Nanoparticles with Denderimeric Linkers and Its Application for Microextraction Purposes, One-Pot Preparation of Pyrans Pigments and Removal of Malachite Green,” Journal of the Taiwan Institute of Chemical Engineers 118 (2021): 342–54. (e) B. Maleki, H. Atharifar, O. Reiser, and R. Sabbaghzadeh, “Glutathione-Coated Magnetic Nanoparticles for One-Pot Synthesis of 1,4-Dihydropyridine Derivatives,” Polycyclic Aromatic Compounds 41, no. 4 (2021): 721–34. (f) B. Maleki, D. Azarifar, R. Ghorbani-Vaghei, H. Veisi, S.F. Hojati, M. Gholizadeh, H. Salehabadi, and M. Khodaverdian Moghadam, “1,3-Dibromo-5,5-Dimethylhydantoin or N-Bromosuccinimide as Efficient Reagents for Chemoselective Deprotection of 1,1-Diacetates under Solvent-Free Conditions,” Monatshefte Für Chemie-Chemical Monthly 140 (2009): 1485–88. (g) S. Sajjadifa, I. Amini, S. Habibzadeh, Gh Mansouri, and E. Ebadi, “Acidic Ionic Liquid Based Silica-Coated Fe3O4 Nanoparticles as a New Nanomagnetic Catalyst for Preparation of Aryl and Heteroaryl Thiocyanates,” Chemical Methodologies 4, no. 5 (2020): 623–34. (h) A. Khazaei, F. Gohari-Ghalil, M. Tavasoli, M. Rezaei-Gohar, and A.R. Moosavi-Zare, “Fe3O4 Bonded Pyridinium-3-Carboxylic acid-N-Sulfonic Acid Chloride as an Efficient Catalyst for the Synthesis of 3,4-Dihydropyrimidin-2(1H)-Ones,” Chemical Methodologies 4, no. 5 (2020): 543–53. (i) A. Khazaei, A.R. Moosavi-Zare, H. Afshar-Hezarkhani, and V. Khakyzadeh, “Programming of Fe-Catalyzed Cascade Knoevenagel-Michael-Cyclocondensation Reaction: Create out Pseudo Acridine Derivatives under Solvent Free Conditions,” Eurasian Chemical Communications 2, no. 1 (2020): 27–34. (j) S. Sajjadifar, I. Amini, S. Habibzadeh, G. Mansouri, and E. Ebadi, “Acidic Ionic Liquid Based Silica-Coated Fe3O4 Nanoparticles as a New Nanomagnetic Catalyst for Preparation of Aryl and Heteroaryl Thiocyanates,” Chemical Methodologies 4, no. 5 (2020): 623–634. (k) F. Mostaghni, and F. Taat, “CoFe2O4 as Green and Efficient Catalyst for Synthesis of Multisubstituted Imidazoles,” Eurasian Chemical Communications 2, no. 4 (2020): 427–32. (l) A.H. Karimi, A. Hekmat-Ara, A. Zare, M. Barzegar, R. Khanivar, and M. Sadeghi-Takallo, “Producing, Characterizing and Utilizing a Novel Magnetic Catalyst to Promote Construction of N,N′-Alkylidene Bisamides,” Eurasian Chemical Communications 3, no. 6 (2021): 360–68. (m) S. Sajjadifar, I. Amini, G. Mansouri, and S. Alimohammadi, “Fe3O4@APTES@isatin-SO3H as Heterogeneous and Efficient Catalyst for the Synthesis of Quinoxaline Derivatives,” Eurasian Chemical Communications 2, no. 5 (2020): 626–33.
  • R.S. Ribeiro, A.M.T. Silva, J.L. Figueiredo, J.L. Faria, and H.T. Gomes, “Catalytic Wet Peroxide Oxidation: A Route towards the Application of Hybrid Magnetic Carbon Nanocomposites for the Degradation of Organic Pollutants, a Review,” Applied Catalysis B: Environmental 187 (2016): 428–60.
  • A. Majouga, M. Sokolsky-Papkov, A. Kuznetsov, D. Lebedev, M. Efremova, E. Beloglazkina, P. Rudakovskaya, M. Veselov, N. Zyk, Y. Golovin, et al., “Enzyme-Functionalized Gold-Coated Magnetite Nanoparticles as Novel Hybrid Nanomaterials: Synthesis, Purification and Control of Enzyme Function by Low-Frequency Magnetic Field,” Colloids and Surfaces. B, Biointerfaces 125 (2015): 104–9.
  • B.K. Purushothaman, M. Harsha, S.P.U. Maheswari, and K.M.M.S. Begum, “Magnetic Assisted Curcumin Drug Delivery Using Folate Receptor Targeted Hybrid Caseincalcium Ferrite Nanocarrier,” Journal of Drug Delivery Science and Technology 52 (2019): 509–20.
  • M. Ahmadi, H. Elmongy, T. Madrakian, and M. Abdel-Rehim, “Nanomaterials as Sorbents for Sample Preparation in Bioanalysis: A Review,” Analytica Chimica Acta 958 (2017): 1–21.
  • R.S. García, S. Stafford, and Y.K. Gun′ko, “Recent Progress in Synthesis and Functionalization of Multimodal Fluorescent-Magnetic Nanoparticles for Biological Applications,” Applied Sciences 8, no. 2 (2018): 172.
  • F.M. Kievit, and M. Zhang, “Surface Engineering of Iron Oxide Nanoparticles for Targeted Cancer Therapy,” Accounts of Chemical Research 44, no. 10 (2011): 853–62.
  • E. Agostinelli, F. Vianello, G. Magliulo, T. Thomas, and T.J. Thomas, “Nanoparticle Strategies for Cancer Therapeutics: Nucleic Acids, Polyamines, Bovine Serum Amine Oxidase and Iron Oxide Nanoparticles (Review),” International Journal of Oncology 46, no. 1 (2015): 5–16.
  • H.P. Feng, L. Tang, G.M. Zeng, Y. Zhou, Y.C. Deng, X. Ren, B.O. Song, C. Liang, M.Y. Wei, and J.F. Yu, “Core-Shell Nanomaterials: Applications in Energy Storage and Conversion,” Advances in Colloid and Interface Science 267 (2019): 26–46.
  • C. Pereira, R.S. Costa, L. Lopes, B. Bachiller-Baeza, I. Rodríguez-Ramos, A. Guerrero-Ruiz, P.B. Tavares, C. Freire, and A.M. Pereira, “Multifunctional Mixed Valence N-Doped CNT@MFe2O4 Hybrid Nanomaterials: From Engineered Onepot Coprecipitation to Application in Energy Storage Paper Supercapacitors,” Nanoscale 10, no. 26 (2018): 12820–40.
  • Y. Zhao, Q. Zumin, and J. Huang, “Preparation and Analysis of Fe3O4 Magnetic Nanoparticles Used as Targeted-Drug Carriers,” Chinese Journal of Chemical Engineering 16, no. 3 (2008): 451–5.
  • A.R. Sardarian, M. Zangiabadi, I.D. Inaloo, “Fe3O4@SiO2/Schiff Base/Pd Complex as an Efficient Heterogeneous and Recyclable Nanocatalyst for Chemoselective N-Arylation of O-Alkyl Primary Carbamates,” RSC Advances 6, no. 94 (2016): 92057–64.
  • Y.B. Wagh, Y.A. Tayade, S.A. Padvi, B.S. Patil, N.B. Patil, and D.S. Dalal, “A Cesium Fluoride Promoted Efficient and Rapid Multicomponent Synthesis of Functionalized 2-Amino-3-Cyano-4H-Pyran and Spirooxindole Derivatives,” Chinese Chemical Letters 26, no. 10 (2015): 1273–7.
  • G. Zhang, Y. Zhang, J. Yan, R. Chen, S. Wang, Y. Ma, and R. Wang, “One-Pot Enantioselective Synthesis of Functionalized Pyranocoumarins and 2-Amino-4H-Chromenes: Discovery of a Type of Potent Antibacterial Agent,” The Journal of Organic Chemistry 77, no. 2 (2012): 878–88.
  • I. Devi, and P.J. Bhuyan, “Sodium Bromide Catalysed One-Pot Synthesis of Tetrahydrobenzo[b]Pyrans via a Three-Component Cyclocondensation under Microwave Irradiation and Solvent Free Conditions,” Tetrahedron Letters 45, no. 47 (2004): 8625–7.
  • L. Bonsignore, G. Loy, D. Secci, and A. Calignano, “Synthesis and Pharmacological Activity of 2-Oxo-(2H) 1-Benzopyran-3-Carboxamide Derivatives,” European Journal of Medicinal Chemistry 28, no. 6 (1993): 517–20.
  • H. Gourdeau, L. Leblond, B. Hamelin, C. Desputeau, K. Dong, L. Kianicka, D. Custeau, C. Boudeau, L. Geerts, and S.X. Cai, “Microwave Assisted Synthesis of Tetrahydrobenzo[b]Pyrans via One Pot Multicomponent Reaction Using [Et3NH][HSO4] as Ionic Liquid Catalyst,” Journal of Pharmaceutical, Chemical and Biological Sciences 3 (2004): 1375–84.
  • S.A. Patil, R. Patil, L. Pfeffer, and D. Miller, “Chromenes: Potential New Chemotherapeutic Agents for Cancer,” Future Medicinal Chemistry 5, no. 14 (2013): 1647–60.
  • W. Kemnitzer, S. Kasibhatla, S. Jiang, H. Zhang, J. Zhao, S. Jia, L. Xu, C. Crogan-Grundy, R. Denis, N. Barriault, et al., “Discovery of 4-Aryl-4H-Chromenes as a New Series of Apoptosis Inducers Using a Cell- and Caspase-Based High-Throughput Screening Assay. 2. Structure–Activity Relationships of the 7- and 5-, 6-, 8-Positions,” Bioorganic & Medicinal Chemistry Letters 15, no. 21 (2005): 4745–51.
  • J.L. Wang, D. Liu, J.L. Zhang, S. Shan, X. Han, S. Srinivasula, M. Croce, C.M. Alnemri, and E.S. Huang, “Structure-Based Discovery of an Organic Compound That Binds Bcl-2 Protein and Induces Apoptosis of Tumor Cells,” Proceedings of the National Academy of Sciences of the United States of America 97, no. 13 (2000): 7124–9.
  • A. Kulshrestha, G.K. Katara, S.A. Ibrahim, R. Patil, S.A. Patil, and K.D. Beaman, “Microtubule Inhibitor, SP-6-27 Inhibits Angiogenesis and Induces Apoptosis in Ovarian Cancer Cells,” Oncotarget 8, no. 40 (2017): 67017–28.
  • B. Maleki, and S. Sheikh, “One-Pot Synthesis of 2-Amino-2-Chromene and 2-Amino-3-Cyano-4H-Pyran Derivatives Promoted by Potassium Fluoride,” Organic Preparations and Procedures International 47, no. 5 (2015): 368–78.
  • M. Fallah-Mehrjardi, M. Foroughi, and S.H. Banitaba, “Polyethylene Glycol-Bis (N-Methylimidazolium) Dihydroxide as an Efficient and Recyclable Basic Phase-Transfer Catalyst for the Synthesis of 4H-Pyran Derivatives in Aqueous Media,” Asian Journal of Green Chemistry 4 (2020): 75–86.
  • M.G. Dekamin, S.Z. Peyman, Z. Karimi, S. Javanshir, M.R. Naimi-Jamal, and M. Barikani, “Sodium Alginate: An Efficient Biopolymeric Catalyst for Green Synthesis of 2-Amino-4H-Pyran Derivatives,” International Journal of Biological Macromolecules 87 (2016): 172–9.
  • B. Baghernejad, and M. Fiuzat, “Synthesis of 2-Amino-4H-Pyran Derivatives in Aqueous Media with nano-SnO2 as Recyclable Catalyst,” Asian Journal of Nanoscience and Materials 4 (2021): 171–7.
  • S. Mozaffarnia, R. Teimuri-Mofrad, and M.R. Rashidi, “Synthesis of 2-Amino-3-Cyano-4H-Pyran Derivatives Using GO-Fc@Fe3O4 Nanohybrid as a Novel Recyclable Heterogeneous Nanocatalyst and Preparation of Tacrine-Naphthopyran Hybrids as AChE Inhibitors,” Journal of the Iranian Chemical Society 18, no. 6 (2021): 1455–70.
  • V.P. Pagore, V.B. Jadhav, P.N. Bajad, and R.P. Pawar, “Rapid and Green Synthesis of Tetrahydrobenzo[b]Pyran Derivatives Using Reusable [EMIM][OH] Ionic Liquid,” Asian Journal of Green Chemistry 4 (2020): 379–86.
  • D.D. Pham, G. Vo-Thanh, and T.N. Le, “Efficient and Green Synthesis of 4H-Pyran Derivatives under Ultrasound Irradiation in the Presence of K2CO3 Supported on Acidic Montmorillonite,” Synthetic Communications 47, no. 18 (2017): 1684–91.
  • A. Molla, and S. Hussain, “Base Free Synthesis of Iron Oxide Supported on Boron Nitride for the Construction of Highly Functionalized Pyrans and Spirooxindoles,” RSC Advances 6, no. 7 (2016): 5491–502.
  • H. Aghahosseini, M.R. Ranjbar, and A. Ramazani, “Simple and Efficient Synthesis of Guanidine-Based Magnetic Nanocatalyst for the One-Pot, Four-Component Synthesis of Polyhydroquinolines in Water,” ChemistrySelect 5, no. 28 (2020): 8415–20.
  • E Pourian, S Javanshir, Zahra Dolatkhah, Shiva Molaei, and Ali Maleki, “Ultrasonic-Assisted Preparation, Characterization, and Use of Novel Biocompatible Core/Shell Fe3O4@GA@Isinglass in the Synthesis of 1,4-Dihydropyridine and 4H‑Pyran Derivatives,” ACS Omega. 3, no. 5 (2018): 5012–20.
  • H. Taherkhani, A. Ramazani, S. Sajjadifar, H. Aghahosseini, A. Rezaei, and S. Rezayati, “Grinding Synthesis of 2-Amino-4H-Benzo[b]Pyran Derivatives Catalyzed by Highly Efficient GPTMS/Guanidine Protected Magnetic Nanoparticles,” ChemistrySelect 6, no. 41 (2021): 11362–74.
  • S. Rezayati, A. Ramazani, S. Sajjadifar, H. Aghahosseini, and A. Rezaei, “Design of a Schiff Base Complex of Copper Coated on EpoxyModified Core − Shell MNPs as an Environmentally Friendly and Novel Catalyst for the One-Pot Synthesis of Various ChromeneAnnulated Heterocycles,” ACS Omega 6, no. 39 (2021): 25608–22.
  • H. Mohamadi Tanuraghaj, and M. Farahi, “Preparation, Characterization and Catalytic Application of nano-Fe3O4@SiO2@(CH2)3OCO 2Na as a Novel Basic Magnetic Nanocatalyst for the Synthesis of New Pyranocoumarin Derivatives,” RSC Advances 8, no. 49 (2018): 27818–24.
  • M. Mirzaee, B. Bahramian, P. Gholampour, S. Teymouri, and T. Khorsand, “Preparation and Characterization of Fe3O4@Boehmite Core-Shell Nanoparticles to Support Molybdenum or Vanadium Complexes for Catalytic Epoxidation of Alkenes,” Applied Organometallic Chemistry 33, no. 4 (2019): e4792.
  • Abdolkarim Zare, Alireza Kohzadian, Zahra Abshirini, Seyed Sajad Sajadikhah, Joshua Phipps, Mourad Benamara, and M. Hassan Beyzavi, “Nano-2-(Dimethylamino)-N-(Silica-n-Propyl)-N,N-Dimethylethanaminium Chloride as a Novel Basic Catalyst for the Efficient Synthesis of Pyrido[2,3-d:6,5-d0]-Dipyrimidines,” New Journal of Chemistry 43, no. 5 (2019): 2247–57.
  • F. Kalantari, A. Ramazani, M.R. Poor Heravi, H. Aghahosseini, and K. Ślepokura, “Magnetic Nanoparticles Functionalized with Copper Hydroxyproline Complexes as an Efficient, Recoverable, and Recyclable Nanocatalyst: Synthesis and Its Catalytic Application in a Tandem Knoevenagel–Michael Cyclocondensation Reaction,” Inorganic Chemistry 60, no. 19 (2021): 15010–23.
  • P. Singh, P. Yadav, A. Mishra, and S.K. Awasthi, “Green and Mechanochemical One-Pot Multicomponent Synthesis of Bioactive 2‑Amino‑4H‑Benzo[b]Pyrans via Highly Efficient AmineFunctionalized SiO2@Fe3O4 Nanoparticles,” ACS Omega. 5, no. 8 (2020): 4223–32.
  • B. Maleki, and S.S. Ashrafi, “Nano α-Al2O3 Supported Ammonium Dihydrogen Phosphate (NH4H2PO4/Al2O3): Preparation, Characterization and Its Application as a Novel and Heterogeneous Catalyst for the One-Pot Synthesis of Tetrahydrobenzo [b] Pyran and Pyrano [2, 3-c] Pyrazole Derivatives,” RSC Advances 4, no. 81 (2014): 42873–91.
  • G. Sabitha, K. Arundhathi, K. Sudhakar, B. Sastry, and J. Yadav, “Cerium (III) Chloride–Catalyzed One-Pot Synthesis of Tetrahydrobenzo [b] Pyrans,” Synthetic Communications 39, no. 3 (2009): 433–42.
  • B. Maleki, M. Baghayeri, S. A. J. Abadi, R. Tayebee, and A. Khojastehnezhad, “Ultrasound Promoted Facile One Pot Synthesis of Highly Substituted Pyran Derivatives Catalyzed by Silic-acoated Magnetic NiFe2O4 Nanoparticle-Supported H14[NaP5W30O110] under Mild Conditions,” RSC Advances 6, no. 99 (2016): 96644–61.
  • S. F. Hojati, A. Amiri, N. MoeiniEghbali, and S. Mohamadi, “Polypyrrole/Fe3O4/CNT as a Recyclable and Highly Efficient Catalyst for Onepot Three-Component Synthesis of Pyran Derivatives,” Applied Organometallic Chemistry 32, no. 4 (2018): e4235.
  • R. S. Bhosale, C. V. Magar, K. S. Solanke, S. B. Mane, S. S. Choudhary, and R. P. Pawar, “Molecular Iodine: An Efficient Catalyst for the Synthesis of Tetrahydrobenzo [b] pyrans,” Synthetic Communications 37, no. 24 (2007): 4353–57.
  • A. Mohammadzadeh, A. P. Marjani, and A. Zamani, “A Novel Biopolymer-Based Nanomagnetic Catalyst for the Synthesis of 4H-Pyran and Tetrahydro-4H-Chromene Derivatives,” South African Journal of Chemistry 73 (2020): 55–63.
  • A. Alizadeh, M. M. Khodaei, M. Beygzadeh, D. Kordestani, and M. Feyzi, “Biguanide-Functionalized Fe3O4/SiO2 Magnetic Nanoparticles: An Efficient Heterogeneous Organosuperbase Catalyst for Various Organic Transformations in Aqueous Media,” Bulletin of the Korean Chemical Society 33, no. 8 (2012): 2546–52.
  • I. A. Azath, P. Puthiaraj, and K. Pitchumani, “One-Pot Multicomponent Solvent-Free Synthesis of 2-Amino-4H-Benzo [b] Pyrans Catalyzed by per-6-Amino-β-Cyclodextrin,” ACS Sustainable Chemistry and Engineering 1, no. 1 (2013): 174–79.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.