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Research Articles

Boric Acid/Pentaerythritol as a Green and Reusable Catalytic System for the Synthesis of Mono- and Bis-Pyrano[2,3-d]Pyrimidinone Derivatives in Water

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Pages 6458-6469 | Received 25 May 2022, Accepted 18 Aug 2022, Published online: 06 Sep 2022

References

  • S. Mashkouri, and M. R. Naimi-Jamal, “Mechanochemical Solvent-Free and Catalyst-Free One-Pot Synthesis of Pyrano, [2,3-d]Pyrimidine-2,4(1H,3H)-Diones with Quantitative Yields,” Molecules 14, no. 1 (2009): 474–9.
  • N. Irannejad-Gheshlaghchaei, A. Zare, A. Banaei, H. Kaveh, and N. Varavi, Department of Chemistry, Payame Noor University, P.O. Box 19395-3697, Tehran, Iran, ‎“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): 400–7.
  • 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.
  • 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.
  • J. Albadi, H. A. Samimi, and A. Momeni, “Alumina-Supported Cobalt Nanoparticles Efficiently Catalyzed the Synthesis of Chromene Derivatives under Solvent-Free Condition,” Chemical Methodologies 4 (2020): 565–71.
  • S. Rezayati, A. Ramazani, S. Sajjadifar, H. Aghahosseini, and A. Rezaei, “Design of a Schiff Base Complex of Copper Coated on Epoxy-Modified Core-Shell MNPs as an Environmentally Friendly and Novel Catalyst for the One-Pot Synthesis of Various Chromene-Annulated Heterocycles,” ACS Omega 6, no. 39 (2021): 25608–22.
  • M. S. Mohamed, R. Kamel, and S. S. Fatahala, “Synthesis and Biological Evaluation of Some Thio Containing Pyrrolo[2,3-d]Pyrimidine Derivatives for Their Anti-Inflammatory and Anti-Microbial Activities,” European Journal of Medicinal Chemistry 45, no. 7 (2010): 2994–3004.
  • A. M. Fargualy, N. S. Habib, K. A. Ismail, A. M. M. Hassan, and M. T. M. Sarg, “Synthesis, Biological Evaluation and Molecular Docking Studies of Some Pyrimidine Derivatives,” European Journal of Medicinal Chemistry 66 (2013): 276–95.
  • 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.
  • F. Mohamadpour, “Catalyst-Free Three-Component Tandem Green Synthesis of Pyran [2,3-d] Pyrimidine Scaffolds in Ethylene Glycol (E-G) as a Recyclable Reaction Medium,” Polycyclic Aromatic Compounds 40 (2020).
  • R. Azimi, R. Baharfar, and H. Bagheri, “Stereoselective Synthesis of Multifunctional Spirooxindole-Dihydrofuran Derivatives,” Polycyclic Aromatic Compounds 41 (2021): 1–10.
  • M. Dadaei, and H. Naeimi, “Guanidine Functionalized Core–Shell Structured Magnetic Cobalt-Ferrite as an Efficient Nanocatalyst for Sonochemical Synthesis of Spirooxindoles in Water,” RSC Advances 11, no. 25 (2021): 15360–8.
  • A. Maleki, Z. Hajizadeh, and K. Valadi, “Green and Eco-Friendly Mica/Fe3O4 as an Efficient Nanocatalyst for the Multicomponent Synthesis of 2-Amino-4H-Chromene Derivatives,” Green Chemistry Letters and Reviews 14, no. 1 (2021): 62–72.
  • A. Amininia, K. Pourshamsian, and B. Sadeghi, “Nano-ZnO Impregnated on Starch—a Highly Efficient Heterogeneous Bio-Based Catalyst for One-Pot Synthesis of Pyranopyrimidinone and Xanthene Derivatives as Potential Antibacterial Agents,” Russian Journal of Organic Chemistry 56, no. 7 (2020): 1279–88.
  • G. Mohammadi Ziarani, S. Faramarzi, S. Asadi, A. Badiei, R. Bazl, and M. Amanlou, “Three-Component Synthesis of Pyrano[2,3-d]-Pyrimidine Dione Derivatives Facilitated by Sulfonic Acid Nanoporous Silica (SBA-Pr-SO3H) and Their Docking and Urease Inhibitory Activity,” Daru 21, no. 1 (2013): 1–13.
  • S. Jain, P. K. Paliwal, G. N. Babu, and A. Bhatewara, “DABCO Promoted One-Pot Synthesis of Dihydropyrano(c)Chromene and Pyrano[2,3-d]Pyrimidine Derivatives and Their Biological Activities,” Journal of Saudi Chemical Society 18, no. 5 (2014): 535–40.
  • O. Goli Jolodar, F. Shirini, and M. Seddighi, “Efficient Synthesis of Pyrano[2,3‐d]Pyrimidinone and Pyrido[2,3‐d]Pyrimidine Derivatives in Presence of Novel Basic Ionic Liquid Catalyst,” Chinese Journal of Catalysis 38, no. 7 (2017): 1245–51.
  • J. Yu, and H. Wang, “Green Synthesis of Pyrano[2,3-d]Pyrimidine Derivatives in Ionic Liquids,” Synthetic Communications 35, no. 24 (2005): 3133–40.
  • A. R. Bhat, A. H. Shalla, and R. S. Dongre, “Dibutylamine (DBA): a Highly Efficient Catalyst for the Synthesis of Pyrano[2,3-d]Pyrimidine Derivatives in Aqueous Media,” Journal of Taibah University for Science 10, no. 1 (2016): 9–18.
  • M. M. Zeydi, and M. Sedighi Gildeh, “γ-Fe2O3@KSF: A Recyclable Catalyst for the Efficient Synthesis of Pyrano-Pyrimidinone Derivatives,” International Journal of New Chemistry 5, no. 4 (2018): 159–71.
  • M. M. Heravi, A. Ghods, K. Bakhtiari, and F. Derikvand, “Zn[(L)Proline] 2: An Efficient Catalyst for the Synthesis of Biologically Active Pyrano[2,3-d]Pyrimidine Derivatives,” Synthetic Communications 40, no. 13 (2010): 1927–31.
  • I. Devi, B. S. D. Kumar, and P. J. Bhuyan, “A Novel Three Component One-Pot Synthesis of Pyrano[2,3-d]Pyrimidines and Pyrido[2,3-d]Pyrimidines Using Microwave Heating in the Solid State,” Tetrahedron Letters 44, no. 45 (2003): 8307–10.
  • A. Mobinikhaledi, N. Foroughifar, and M. A. Bodaghi Fard, “Eco-Friendly and Efficient Synthesis of Pyrano[2,3-d]Pyrimidinone and Tetrahydrobenzo[b]Pyran Derivatives in Water,” Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal 40, no. 3 (2010): 179–85.
  • A. A. Shestopalov, L. A. Rodinovskaya, A. M. Shestopalov, and V. P. Litvinov, “Single-Step Synthesis of Substituted 7-Aminopyrano[2,3-d]Pyrimidines,” Russian Chemical Bulletin 53, no. 10 (2004): 2342–4.
  • A. Maleki, A. A. Jafari, and S. Yousefi, “Green Cellulose-Based Nanocomposite Catalyst: Design and Facile Performance in Aqueous Synthesis of Pyranopyrimidines and Pyrazolopyranopyrimidines,” Carbohydrate Polymers 175 (2017): 409–16.
  • H. Kefayati, M. Valizadeh, and A. Islamnezhad, “Green Electrosynthesis of Pyrano[2,3-d]Pyrimidinones at Room Temperature,” Analytical and Bioanalytical Electrochemistry 6, no. 1 (2014): 80–90.
  • J. Albadi, A. Mansournezhad, and T. Sadeghi, “Eco-Friendly Synthesis of Pyrano[2,3-d]Pyrimidinone Derivatives Catalyzed by a Novel Nanocatalyst of Zno-Supported Copper Oxide in Water,” Research on Chemical Intermediates 41, no. 11 (2015): 8317–26.
  • A. Khazaei, H. A. A. Nik, and A. R. Moosavi-Zare, “Water Mediated Domino Knoevenagel-Michael-Cyclocondensation Reaction of Malononitrile, Various Aldehydes and Barbituric Acid Derivatives Using Boric Acid Aqueous Solution System Compared with Nano-Titania Sulfuric Acid,” Journal of the Chinese Chemical Society 62, no. 8 (2015): 675–9.
  • P. Rammohan, “Boric Acid in Organic Synthesis: Scope and Recent Developments,” Arkivoc 1 (2018): 346–71.
  • L. Orthner, and G. Freyss, “Beitrtrӓge Zur Stereochemie Organischer Verbindungen. II. Über Die Rӓgumliche Anordnung Der Atome im Pentaerythritmolekül,” Justus Liebig’s Annalen Der Chemie 484, no. 1 (1930): 131–54.
  • S. F. Marrian, “The Chemical Reactions of Pentaerythritol and Its Derivatives,” Chemical Reviews 43, no. 1 (1948): 149–202.
  • W. Slough, and W. F. Perger, “Application of an Empirical Dispersion Potential to Van Der Waals Binding in Nitromethane, Pentaerythritol, and Pentaerythritol Tetranitrate,” Chemical Physics Letters 498, no. 1-3 (2010): 97–100.
  • B. Pani, S. Sirohi, and D. Singh, “Studies on the Effects of Various Flame Retardants on Polypropylene,” Materials Science 3, no. 4 (2013): 63–9.
  • S. Decato, T. Bemis, E. Madsen, and S. Mecozzi, “Synthesis and Characterization of Perfluoro-Tertbutyl Semifluorinated Amphiphilic Polymers and Their Potential Application in Hydrophobic Drug Delivery,” Polymer Chemistry 5, no. 22 (2014): 6461–71.
  • G. V. Barabanova, A. K. Klimov, V. I. Ivanov, L. V. Kossova, F. S. Vilenchuk, and G. F. Bebikh, “Derivatives of 1,3-Pyrimidine-Thione (5,6-Dihydro-2(1H)-Pyrimidinethione) as Additives for Synthetic Lubricating Oils,” Chemistry and Technology of Fuels and Oils 16, no. 12 (1980): 780–2.
  • M. Ge, J. T. Miao, K. Zhang, Y. Wu, L. Zheng, and L. Wu, “Building Biobased, Degradable, Flexible Polymer Networks from Vanillin via Thiol–Ene ‘Click’ Photopolymerization,” Polymer Chemistry 12, no. 4 (2021): 564–71.
  • H. R. Safaei, M. Shekouhy, S. Rahmanpur, and A. Shirinfeshan, “Glycerol as a Biodegradable and Reusable Promoting Medium for the Catalyst-Free One-Pot Three Component Synthesis of 4H-Pyrans,” Green Chemistry 14, no. 6 (2012): 1696–704.
  • S. Farahmand, R. Ayazi, ‑Nasrabadi, M. Mokhlesi, and M. A. Zolfigol, ““Pentaerythritol as Efficient H-Bonding Organocatalyst for Synthesis of Indazolo[2,1-b]Phthalazine-Trione Derivatives,” Research on Chemical Intermediates 45, no. 7 (2019): 3795–807.
  • C. Mukhopadhyay, and A. Datta, “Synthesis of Substituted Pyrimidinones Catalyzed by Boric Acid and Glycerol in Aqueous Medium,” Synthetic Communications 43, no. 3 (2013): 438–49.
  • S. J. Tu, X. T. Zhu, F. Fang, X. J. Zhang, S. L. Zhu, T. J. Li, D. Q. Shi, X. S. Wang, and S. J. Ji, “One-Pot Synthesis of Bis(Dihydropyrimidinone-4-Yl)Benzene Using Boric Acid as a Catalyst,” Chinese Journal of Chemistry 23 (2005): 596–8.
  • P. V. Shinde, S. S. Sonar, B. B. Shingate, and M. S. Shingare, “Boric Acid Catalyzed Convenient Synthesis of 2-Amino-3,5-Dicarbonitrile-6-Thio-Pyridines in Aqueous Media,” Tetrahedron Letters 51, no. 9 (2010): 1309–12.
  • S. L. Jain, S. Singhal, and B. Sain, “PEG-Assisted Solvent and Catalyst Free Synthesis of 3,4-Dihydropyrimidinones under Mild Reaction Conditions,” Green Chemistry 9, no. 7 (2007): 740–1.
  • M. E. Wilhelm, M. H. Anthofer, M. Cokoja, and I. I. E. Markovits, W. A. Herrmann, and F. E. Kuhn, “Cycloaddition of Carbon Dioxide and Epoxides Using Pentaerythritol and Halides as Dual Catalyst System,” Chemsuschem. 7, no. 5 (2014): 1357–60.

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