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Research Articles

Poly(4-Vinylpyridine) (P4VPy): A Basic Catalyst for Facile Synthesis of Biscoumarin and Dihydropyrano[3,2-c]Chromene Derivatives in Aqueous Media

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Pages 199-210 | Received 27 Nov 2018, Accepted 19 Jan 2019, Published online: 26 Feb 2019

References

  • J. Safaei-Ghomi, F. Eshteghal, and M.A. Ghasemzadeh, “Solvent-Free Synthesis of Dihydropyrano[3,2-c]Chromene and Biscoumarin Derivatives Using Magnesium Oxide Nanoparticles as a Recyclable Catalyst,” Acta Chimica Slovenica  61 (2014): 703–8.
  • M.G. Dekamin, M. Eslami, and A. Maleki, “Potassium Phthalimide-N-oxyl: A Novel, Efficient, and Simple Organocatalyst for the One-pot Three-component Synthesis of Various 2-Amino-4h-Chromene Derivatives in Water,”Tetrahedron 69, no. 3 (2013): 1074–85.
  • S.S. Mansoor, K. Logaiya, K. Aswin, and P.N. Sudhan, “An Appropriate One-Pot Synthesis of 3,4 Dihydropyrano[c]Chromenes and 6-Amino-5-Cyano-4-aryl-2-Methyl-4H-Pyrans Using Thiourea Dioxide as an Efficient and Reusable Organocatalyst in Aqueous Medium,”  Journal of Taibah University Medical Sciences 9, no. 2 (2015): 213–26.
  • Okenne, R., R.D. Thomes, Coumarins: Biology Application and Modes of Action (Chichester, UK: Wiley & Sons, 1997).
  • Zahradnik, M. The Production and Application of Fluorescent Brightening Agents (Chichester, UK: Wiley & Sons, 1992).
  • D.C. Mungra, M.P. Patel, D.P. Rajani, and R.G. Patel, “Synthesis and Identification of b-aryloxyquinolines and Their Pyrano[3,2-c]Chromene Derivatives as a New Class of Antimicrobial and Antituberculosis Agents,” European Journal of Medicinal Chemistry 46, no. 9 (2011): 4192–200.
  • G. Cingolani, F. Gualtieri, and M. Pigini, “Researches in the Field of Antiviral Compounds. Mannich Bases of 3-Hydroxy Coumarin,” Journal of Medicinal Chemistry 12, no. 3 (1969): 531–2.
  • C. Biot, G. Glorian, L.A. Maciejewski, J.S. Brocard, O. Domarle, G. Blampain, P. Millet, A.J. Georges, H. Abessolo, D. Dive, et al. “Synthesis and Antimalarial Activity in Vitro and in Vivo of a New Ferrocene-chloroquine Analogue,” Journal of Medicinal Chemistry 40, no. 23 (1997): 3715–8.
  • J. Neyts, E.D. Clercq, R. Singha, Y.H. Chang, A.R. Das, S.K. Chakraborty, S.C. Hong, S.-C. Tsay, M.-H. Hsu, and J.R. Hwu, “Structure-Activity Relationship of New anti-hepatitis C Virus Agents: Heterobicycle-Coumarin Conjugates,” Journal of Medicinal Chemistry 52, no. 5 (2009): 1486–90.
  • T.A. Bayer, S. Schafer, H. Breyh, O. Breyhan, C. Wirths, and G.A. Treiber, “A Vicious Circle: role of Oxidative Stress, intraneuronal Abeta and Cu in Alzheimer's disease,” Clinical Neuropathology 25, no. 4 (2006): 163–71.
  • I. Kostava, I. Manolov, I. Nicolova, S. Konstantonov, and M. Karaivanova, “New Lanthanide Complexes of 4-Methyl-7-Hydroxycoumarin and Their Pharmacological Activity,” European Journal of Medicinal Chemistry 36 (2001): 339–47.
  • E.A.A. Hafez, M.H. Elnagdi, A.G.A. Elagamey, and F.M.A.A. EL-Taweel, “Nitrues in Heterocyclyc Synthesis: Novel Synthesis of Benzoyl-coumarin and of Benzo[c]Pyrano[3,2-c]Quinolone Derivatives,” Journal of Heterocyclic Chemistry 26 (1987): 903–7.
  • A. Tanabe, H. Nakashima, O. Yoshida, N. Yamamoto, O. Tenmyo, and T. Oki, “Inhibitory Effect of New Antibiotic, Pradimicin A On Infectivity, Cytopathic Effect and Replication of Human Immunodeficiency Virus in Vitro,” The Journal of Antibiotics 41, no. 11 (1988): 1708–10.
  • A. Bolognese, G. Correale, M. Manfra, A. Lavecchia, O. Mazzoni, E. Novellino, P. La Colla, G. Sanna, and R. Loddo, “Antitumor Agents. 3. Design, Synthesis, and Biological Evaluation of New Pyridoisoquinolindione and Dihydrothienoquinolindione Derivatives with Potent Cytotoxic Activity,” Journal of Medicinal Chemistry 47, no. 4 (2004): 849–58.
  • G.P. Ellis, The Chemistry of Heterocyclic Compounds in Chromenes, vol. 2 (New York, NY: John Wiley, 1977), 13–5.
  • A.A. Aziem, “Synthesis and Antimicrobial Activity of Some Novel Thiazoles, 1,3,4‐Thiadiazines, 1,3,4‐Thiadiazoles Incorporating Coumarin Moiety,” Journal of Heterocyclic Chemistry 52 (2015): 251–3.
  • J.M. Khurana and S. Kumar, “Ionic Liquid: An Efficient and Recyclable Medium for the Synthesis of Octahydroquinazolinone and Biscoumarin Derivatives,” Monatshefte Für ChemieChemical Monthly 141, no. 5 (2010): 561–4.
  • H. Mehrabi and H. Abusaidi, “Synthesis of Biscoumarin and 3,4-Dihydropyrano[c]Chromene Derivatives Catalysed by Sodium Dodecyl Sulfate (SDS) in Neat Water,” Journal of the Iranian Chemical Society 7, no. 4 (2010): 890–4.
  • A. Zhu, Sh Bai, L. Li, M. Wang, and J. Wang, “Choline Hydroxide: An Efficient and Biocompatible Basic Catalyst for the Synthesis of Biscoumarins under Mild Conditions." Catalysis Letters 145 (2015): 1089–93.
  • A. Kiasat and L. Hemat-Alian, “Phospho Sulfonic Acid: A Versatile and Efficient Solid Acid Catalyst for Facile Synthesis of Bis-(4-hydroxycoumarin-3-yl) Methanes under Solvent-free Conditions,” Research on Chemical Intermediates 41, no. 2 (2015): 873–80.
  • J.M. Khurana and S. Kumar, “Tetrabutylammonium Bromide (TBAB): A Neutral and Efficient Catalyst for the Synthesis of Biscoumarin and 3,4-Dihydropyrano[c]Chromene Derivatives in Water and Solvent-free Conditions,” Tetrahedron Letters 50, no. 28 (2009): 4125–7.
  • H. Nagabhushana, S.S. Saundalkar, L. Muralidhar, B.M. Nagabhushana, C.R. Girija, D. Nagaraja, M.A. Pasha, and V.P. Jayashankara, “A-Fe2O3 Nanoparticles: An Efficient, Inexpensive Catalyst for the One-Pot Preparation of 3,4-Dihydropyrano[c]Chromenes,” Chinese Chemical Letters 22, no. 2 (2011): 143–6.
  • M. Seifi and H. Sheibani, “High Surface Area MgO as a Highly Effective Heterogeneous Base Catalyst for Three-component Synthesis of Tetrahydrobenzopyran and 3,4-Dihydropyrano[c]Chromene Derivatives in Aqueous Media,” Catalysis Letters 126, no. 3–4 (2008): 275–9.
  • R. Karimian, F. Piri, A.A. Safari, and S.J. Davarpanah, “One-Pot and Chemoselective Synthesis of Bis(4-hydroxycoumarin) Derivatives Catalyzed by Nano Silica Chloride,” Journal of Nanostructure in Chemistry 3, no. 1 (2013): 52–8.
  • K. Niknam and A. Jamali, “Silica-Bonded N-Propylpiperazine Sodium n-Propionate as Recyclable Basic Catalyst for Synthesis of 3,4-Dihydropyrano[c]Chromene Derivatives and Biscoumarins,” Chinese Journal of Catalysis 33, no. 11–12 (2012): 1840–9.
  • H. Mehrabi and M. Kazemi-Mireki, “CuO Nanoparticles: An Efficient and Recyclable Nanocatalyst for the Rapid and Green Synthesis of 3,4-dihydropyrano[c]Chromenes,” Chinese Chemical Letters 22, no. 12 (2011): 1419–22.
  • J. Zheng and L. Yi-Qun, “One-pot Synthesis of Tetrahydrobenzo[b]pyran and Dihydropyrano[c]chromene Derivatives in Aqueous Media by Using Trisodium Citrate as a Green Catalyst,” Archives of Applied Science Research 3, no. 2 (2011): 381–8.
  • A.T. Khan, M. Lal, S. Ali, and M.M. Khan, “One-Pot Three-component Reaction for the Synthesis of Pyran Annulated Heterocyclic Compounds Using DMAP as a Catalyst,” Tetrahedron Letters 52, no. 41 (2011): 5327–32.
  • A.R. Montaghami and N. Montazeri, “An Efficient Method for the One-Pot, Three-Component Synthesis of 3,4-dihydropyrano[c]chromenes Catalyzed by Nano Al2O3,” Oriental Journal of Chemistry 30, no. 3 (2014): 1361–4.
  • K.P. Boroujeni and P. Ghasemi, “Synthesis and Application of a Novel Strong and Stable Supported Ionic Liquid Catalyst with Both Lewis and Brønsted Acid Sites,” Catalysis Communications 37 (2014): 50–4.
  • S. Abdolmohammadi and S. Balalaie, “Novel and Efficient Catalysts for the One-Pot Synthesis of 3,4-dihydropyrano[c]chromene Derivatives in Aqueous Media,” Tetrahedron Letters 48, no. 18 (2007): 3299–303.
  • Y. Wang, H. Ye, G. Zuo, and J. Luo, “Synthesis of a Novel Poly (ethylene Glycol) Grafted N,N-dimethylaminopyridine Functionalized Dicationic Ionic Liquid and Its Application in One-Pot Synthesis of 3,4-dihydropyrano[3,2-c]Chromene Derivatives in Water,” Journal of Molecular Liquids 212 (2015): 418–22.
  • J. Tiwari, M. Saquib, S. Singh, F. Tufail, M. Singh, J. Singh, and J. Singh, “Visible Light Promoted Synthesis of Dihydropyrano[2,3-c]chromenes via a Multicomponent-Tandem Strategy under Solvent and Catalyst Free Conditions,” Green Chemistry 18, no. 11 (2016): 3221–31.
  • M. Farahi, B. Karami, R. Keshavarz, and F. Khosravian, “Nano-Fe3O4@SiO2-supported Boron Sulfonic Acid as a Novel Magnetically Heterogeneous Catalyst for the Synthesis of Pyrano Coumarins,” RSC Advances 7, no. 74 (2017): 46644–50.
  • Y. Pourshojaei, M.H. Jadidi, K. Eskandari, A. Foroumadi, and A. Asadipour, “An Eco-Friendly Synthesis of 4-aryl-substituted Pyranofuzed Coumarins as Potential Pharmacological Active Heterocycles Using Molybdenum Oxide Nanoparticles as an Effective and Recyclable Catalyst,” Research on Chemical Intermediates 44, no. 7 (2018): 4195–212.
  • M. Ghashang, “ZnAl2O4–Bi2O3 Composite Nano-powder as an Efficient Catalyst for the Multi-Component, One-Pot, Aqueous Media Preparation of Novel 4H-chromene-3-Carbonitriles,” Research on Chemical Intermediates 42, no. 5 (2016): 4191–205.
  • M. Ghashang, S.S. Mansoor, L.S. Solaree, and A.S. Esfahani, “Multi-Component, One-Pot, Aqueous Media Preparation of Dihydropyrano [3,2-c]chromene Derivatives over MgO Nanoplates as an Efficient Catalyst,” Iranian Journal of Catalysis 6, no. 3 (2016): 237–43.
  • M. Ghashang, “Bi2O3 Nano-Particles as an Efficient Catalyst for the Multi-component, One-Pot, Aqueous Media Preparation of Benzo[h]pyrano[3,2-c]chromene-2-carbonitriles and Pyrano[3,2-g]chromene-7-Carbonitriles,” Biointerface Research in Applied Chemistry 6, no. 4 (2016): 1338–44.
  • A. Baziar and M. Ghashang, “Preparation of Pyrano[3,2-c]Chromene-3-Carbonitriles Using ZnO Nano-particles: A Comparison between the Box–Behnken Experimental Design and Traditional Optimization Methods,” Reaction Kinetics, Mechanisms and Catalysis 118, no. 2 (2016): 463–79.
  • A. Mobinikhaledi, A. Yazdanipour, and M. Ghashang, “Green Synthesis of 2-Amino-7-Hydroxy-4-aryl-4H-Chromene-3-Carbonitriles Using ZnO Nanoparticles Prepared with Mulberry Leaf Extract and ZnCl2,” Turkish Journal of Chemistry 39, no. 3 (2015): 667–75.
  • M. Ghashang, M. Kargar, M. Shafiee, S. Mansoor, A. Fazlinia, and H. Esfandiari, “CuO Nano-Structures Prepared in Rosmarinus Officinalis Leaves Extract Medium: Efficient Catalysts for the Aqueous Media Preparation of Dihydropyrano[3, 2-c]chromene Derivatives,” Recent Patents on Nanotechnology 9, no. 3 (2015): 204–11.
  • V. Polshettiwar, R. Luque, A. Fihri, H. Zhu, M. Bouhrara, and J.M. Basset, “Magnetically Recoverable Nanocatalysts,” Chemical Reviews 111, no. 5 (2011): 3036–75.
  • R.A. Sheldon, “Catalysis: The Key to Waste Minimization,” Journal of Chemical Technology & Biotechnology 68, no. 4 (1997): 381–8.
  • M.G. Dekamin, N. Yazdaninia, J. Mokhtari, and M.R. Naimi-Jamal, “Tetrabutylammonium phthalimide-N-oxyl: An Efficient Organocatalyst for Trimethylsilylation of Alcohols and Phenols with Hexamethyldisilazane,” Journal of the Iranian Chemical Society 8, no. 2 (2011): 537–44.
  • J. Wu, X. Sun, and Y. Li, “DABCO: An Efficient Organocatalyst in the Ring-opening Reactions of Aziridines with Amines or Thiols,” European Journal of Organic Chemistry 2005, no. 20 (2005): 4271–5.
  • P. Anastas and J. Warner, Green Chemistry: Theory and Practice (New York, NY: Oxford University Press, 1998).
  • J. Albadi and A. Mansournezhad, “Poly(4-vinylpyridine) Efficiently Catalyzed One-pot Four-Component Synthesis of Pyrano[2,3-c]Pyrazoles,” Current Chemistry Letters 3, no. 4 (2014): 221–7.
  • J. Albadi and A. Mansournezhad, “Aqua-mediated Multicomponent Synthesis of Various 4H-pyran Derivatives Catalyzed by Poly (4-vinylpyridine)-Supported Copper Iodide Nanoparticle Catalyst,” Research on Chemical Intermediates 42, no. 6 (2016): 5739–52.
  • F. Shirini, S. Esmaeeli‐Ranjbar, and M. Seddighi, “Poly(4‐vinylpyridinium) Perchlorate as an Efficient and Recyclable Catalyst for the Synthesis of Biscoumarins and Bisindoles,” Chinese Journal of Catalysis 35, no. 7 (2014): 1017–23.
  • F. Shirini and O. Goli-Jolodar, “Introduction of N-sulfonic Acid Poly(4-vinylpyridinum) chloride as an Efficient and Reusable Catalyst for the Chemoselective 1,1-diacetate Protection and Deprotection of Aldehydes,” Journal of Molecular Catalysis A: Chemical 356 (2012): 61–9.
  • F. Shirini, N. Ghaffari-Khaligh, and O. Goli-Jolodar, “An Efficient and Practical Synthesis of Bis(indolyl)methanes Catalyzed by N-sulfonic Acid Poly(4-vinylpyridinium) Chlorid,” Dyes & Pig 98 (2013): 290–6.
  • F. Shirini, N. Ghaffari-Khaligh, and O. Goli-Jolodar, “N-sulfonic Acid Poly(4-vinylpyridinium) chloride: An Efficient and Reusable Solid Acid Catalyst in N-Boc Protection of Amines,” Journal of the Iranian Chemical Society 10, no. 2 (2013): 181–8.
  • G. Brahmachari and B. Banerjee, “Facile and One-pot Access to Diverse and Densely Functionalized 2-Amino-3-Cyano‐4H‐Pyrans and Pyran-annulated Heterocyclic Scaffolds via an Eco-friendly Multicomponent Reaction at Room Temperature Using Urea as a Novel Organo-Catalyst,” ACS Sustainable Chemistry & Engineering 2 (2014): 411–22.
  • S. Jain, D. Rajguru, B.S. Keshwal, and A.D. Acharya, “Solvent-free Green and Efficient One-pot Synthesis of Dihydropyrano[3,2-c]chromene Derivatives,” ISRN Organic Chemistry 2013 (2013): 1–5.
  • K. Tabatabaeian, H. Heidari, M. Mamaghani, and N.O. Mahmoodi, “Ru(II) Complexes Bearing Tertiary Phosphine Ligands: A Novel and Efficient Homogeneous Catalyst for One-pot Synthesis of Dihydropyrano[3,2-c]chromene and Tetrahydrobenzo[b]pyran Derivatives,” Applied Organometallic Chemistry 26, no. 2 (2012): 56–61.
  • J.M. Khurana, B. Nand, and P. Saluja, “DBU: A Highly Efficient Catalyst for One-Pot Synthesis of Substituted 3,4-Dihydropyrano[3,2-c]Chromenes, Dihydropyrano[4,3-B]Pyranes, 2-Amino-4hbenzo[H]Chromenes and 2-Amino-4h Benzo[G]Chromenes in Aqueous Medium,” Tetrahedron 66, no. 30 (2010): 5637–41.
  • G. Mohammadi Ziarani, A. Badiei, M. Azizi, and P. Zarabadi, “Synthesis of 3,4-Dihydropyrano[c]Chromene Derivatives Using Sulfonic Acid Functionalized Silica (SiO2PrSO3H),” Iranian Journal of Chemistry and Chemical Engineering 30 (2011): 59–65.
  • O. Goli-Jolodar, F. Shirini, and M. Seddighi, “Introduction of a Novel Basic Ionic Liquid Containing Dual Basic Functional Groups for the Efficient Synthesis of Spiro-4H-Pyrans,” Journal of Molecular Liquids 224 (2016): 1092–101.
  • A. Millemaggi and R.J. Taylor, “3-Alkenyl-Oxindoles: Natural Products, Pharmaceuticals, and Recent Synthetic Advances in Tandem/telescoped Approaches,” European Journal of Organic Chemistry 2010, no. 24 (2010): 4527–47.
  • J.M. Khurana and K. Vij, “Nickel Nanoparticles: A Highly Efficient Catalyst for One Pot Synthesis of Tetraketones and Biscoumarins,” Journal of Chemical Sciences 124, no. 4 (2012): 907–12.
  • M.A. Zolfigol, A.R. Moosavi-Zare, and M. Zarei, “Friedel-Crafts Alkylation of 4-hydroxycoumarin Catalyzed by Sulfonic-acid-Functionalized Pyridinium Chloride as a New Ionic Liquid,” Comptes Rendus Chimie 17, no. 12 (2014): 1264–8.
  • N. Tavakoli-Hoseini, M.M. Heravi, F.F. Bamoharram, A. Davoodnia, and M. Ghassemzadeh, “An Unexpected Tetracyclic Product Isolated during the Synthesis of Biscoumarins Catalyzed by [MIM(CH2)4SO3H][HSO4]: Characterization and X-ray Crystal Structure of 7-(2-Hydroxy-4-Oxo-4h-Chromen-3-yl)-6H,7H-Chromeno[4,3-b]Chromen-6-One,” Journal of Molecular Liquids 163, no. 3 (2011): 122–7.
  • Z. Karimi-Jaberi, M.R. Nazarifar, and B. Pooladian, “Tris(hydrogensulfato) Boron as a Solid Heterogeneous Catalyst for the Rapid Synthesis of a,a-benzylidene Bis(4-hydroxycoumarin) Derivatives,” Chinese Chemical Letters 23, no. 7 (2012): 781–4.
  • M. Seddighi, F. Shirini, and M. Mamaghani, “Sulfonated Rice Husk Ash (RHA-SO3H) as a Highly Efficient and Reusable Catalyst for the Synthesis of Some Bis-heterocyclic Compounds,” RSC Advances 3, no. 46 (2013): 24046–53.
  • K.M. Khan, S. Iqbal, M.A. Lodhi, G.M. Maharvi, Z. Ullah, M.I. Choudhary, A.-ur Rahman, and S. Perveen, “Biscoumarin: New Class of Urease Inhibitors; Economical Synthesis and Activity,”Bioorganic & Medicinal Chemistry 12, no. 8 (2004): 1963–8.
  • M. Kidwai, V. Bansal, P. Mothsra, S. Saxena, R.K. Somvanshi, S. Dey, and T.P. Singh, “Molecular Iodine: A Versatile Catalyst for the Synthesis of Bis(4-hydroxycoumarin) Methanes in Water,” Journal of Molecular Catalysis A: Chemical 268, no. 1–2 (2007): 76–81.

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