Application of [PVP-SO₃H] HSO₄ as Powerful Polymeric-Based Solid Acid Catalyst for Hantzsch Synthesis of Polyhydrohydroquinolin-5(1H)-One

References

• A. Maleki, M. Ghassemi, and R. Firouzi-Haji, “Green Multicomponent Synthesis of Four Different Classes of Six-Membered N-Containing and O-Containing Heterocycles Catalyzed by an Efficient Chitosan-Based Magnetic Bionanocomposite,” Pure and Applied Chemistry 90 (2018): 387–94.
   Web of Science ®Google Scholar
• H. Wu, Z. Wang, and L. Tao, “The Hantzsch Reaction in Polymer Chemistry: Synthesis and Tentative Application,” Polymer Chemistry 8 (2017): 7290–6.
   Web of Science ®Google Scholar
• A. Sausins and G. Duburs, “Synthesis of 1,4‐Dihydropyridines by Cyclocondensation Reactions,” Chemistry of Heterocyclic Compounds 28 (1992): 363–91.
   Google Scholar
• R. Mannhold, B. Jablonka, B. Voigdt, K. Schoenafinger, and K. Schraven, “Calcium- and Calmodulin-Antagonism of Elnadipine Derivatives: Comparative SAR,” European Journal of Medicinal Chemistry 27 (1992): 229–35.
   Web of Science ®Google Scholar
• T. Godfraind, R. Miller, and M. Wibo, “Calcium Antagonism and Calcium Entry Blockade,” Pharmacological Reviews 38 (1986): 321–416.
   PubMed Web of Science ®Google Scholar
• P. P. Mager, R. A. Coburm, A. J. Solo, D. J. Triggle, and H. Rothe, “QSAR, Diagnostic Statistics and Molecular Modelling of 1,4-Dihydropyridine Calcium Antagonists: A Difficult Road Ahead,” Drug, Design and Discovery 8 (1992): 273–89.
   PubMedGoogle Scholar
• F. R. Bühler and W. Kiowski, “Calcium Antagonists in Hypertension,” Journal of Hypertension 5 (1987): S3–S10.
   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 and Therapeutics 7 (1985): S18–S20.
   Web of Science ®Google Scholar
• I. Pastan and M. Gottesman, “Multiple-Drug Resistance in Human Cancer,” New England Journal of Medicine 316 (1987): 1388–93.
   PubMed Web of Science ®Google Scholar
• H. Ahankar, A. Ramazani, K. Ślepokura, T. Lis, and S. W. Joo, “Synthesis of Pyrrolidinone Derivatives from Aniline, an Aldehyde and Diethyl Acetylenedicarboxylate in an Ethanolic Citric Acid Solution under Ultrasound Irradiation,” Green Chemistry 18 (2016): 3582–93.
   Web of Science ®Google Scholar
• S. T. Fardood, A. Ramazani, Z. Golfar, and S. W. Joo, “Green Synthesis of Ni‐Cu‐Zn Ferrite Nanoparticles Using Tragacanth Gum and Their Use as an Efficient Catalyst for the Synthesis of Polyhydroquinoline Derivatives, ” Applied Organometallic Chemistry 31 (2017): e3823. doi:10.1002/aoc.3823.
   Google Scholar
• A. Hantzsch, “Condensationsprodukte aus Aldehydammoniak und ketonartigen Verbindungen,” European Journal of Inorganic Chemistry 14 (1881): 1637–8.
   Google Scholar
• U. Eisner and J. Kuthan, “Chemistry of Dihydropyridines,” Chemical Reviews 72 (1972): 1–42.
   Web of Science ®Google Scholar
• D. M. Stout and A. Meyers, “Recent Advances in the Chemistry of Dihydropyridines,” Chemical Reviews 82 (1982): 223–43.
   Web of Science ®Google Scholar
• D. Elhamifar, P. Badin, and G. Karimipoor, “Alkyl-Imidazolium Based Organosilica Supported Fe/Porphyrin Complex: As Novel, Highly Efficient and Reusable Catalyst for the Unsymmetrical Hantzsch Reaction,” Journal of Colloid and Interface Science 499 (2017): 120–7.
   PubMed Web of Science ®Google Scholar
• A. Khojastehnezhad, F. Moeinpour, and A. Davoodnia, “PPA-SiO2 Catalyzed Efficient Synthesis of Polyhydroquinoline Derivatives through Hantzsch Multicomponent Condensation under Solvent-Free Conditions,” Chinese Chemical Letters 22 (2011): 807–10.
   Web of Science ®Google Scholar
• B. Das, B. Ravikanth, R. Ramu, and B. V. Rao, “An Efficient One-Pot Synthesis of Polyhydroquinolines at Room Temperature Using HY-Zeolite,” Chemical and Pharmaceutical Bulletin 54 (2006): 1044–5.
   PubMed Web of Science ®Google Scholar
• S. R. Cherkupally and R. Mekala, “p-TSA Catalyzed Facile and Efficient Synthesis of Polyhydroquinoline Derivatives through Hantzsch Multi-component Condensation,” Chemical and Pharmaceutical Bulletin 56 (2008): 1002–4.
   PubMed Web of Science ®Google Scholar
• M. M. Heravi, M. Saeedi, N. Karimi, M. Zakeri, Y. S. Beheshtiha, and A. Davoodnia, “Brønsted Acid Ionic Liquid [(CH2)4SO3HMIM][HSO4] as Novel Catalyst for One-Pot Synthesis of Hantzsch Polyhydroquinoline Derivatives,” Synthetic Communications 40 (2010): 523–9.
   Web of Science ®Google Scholar
• Z. Zarnegar, J. Safari, and Z. Mansouri-Kafroudi, “Environmentally Benign Synthesis of Polyhydroquinolines by Co3O4–CNT as an Efficient Heterogeneous Catalyst,” Catalysis Communications 59 (2015): 216–21.
   Web of Science ®Google Scholar
• L. S. Gadekar, S. S. Katkar, S. R. Mane, B. R. Arbad, and M. K. Lande, “Scolecite Catalyzed Facile and Efficient Synthesis of Polyhydroquinoline Derivatives through Hantzsch Multi-component Condensation,” Bulletin of the Korean Chemical Society 30 (2009): 2532–4.
   Web of Science ®Google Scholar
• M. Maheswara, V. Siddaiah, G. L. V. Damu, and C. V. Rao, “An Efficient One-Pot Synthesis of Polyhydroquinoline Derivatives via Hantzsch Condensation Using a Heterogeneous Catalyst under Solvent-Free Conditions,” ARKIVOC 2 (2006): 201–6.
   Web of Science ®Google Scholar
• N. N. Karade, V. H. Budhewar, S. V. Shinde, and W. N. Jadhav, “L-Proline as an Efficient Organo-Catalyst for the Synthesis of Polyhydroquinoline via Multicomponent Hantzsch Reaction,” Letters in Organic Chemistry 4 (2007): 16–9.
   Web of Science ®Google Scholar
• S. H. Uderji, M. A. Alibeik, and R. R. Karimi, “FSM-16-SO3H Nanoparticles as a Novel Heterogeneous Catalyst: Preparation, Characterization, and Catalytic Application in the Synthesis of Polyhydroquinolines,” Main Group Metal Chemistry 41 (2018): 91–101.
   Web of Science ®Google Scholar
• S. Mondal, B. C. Patra, and A. Bhaumik, “One-Pot Synthesis of Polyhydroquinoline Derivatives through Organic Solid Acid Catalyzed Hantzsch Condensation Reaction,” ChemCatChem 9 (2017): 1469–75.
   Web of Science ®Google Scholar
• M. A. Zolfigol, H. Ghaderi, S. Baghery, and L. Mohammadi, “Nanometasilica Disulfuric Acid (NMSDSA) and Nanometasilica Monosulfuric Acid Sodium Salt (NMSMSA) as Two Novel Nanostructured Catalysts: Applications in the Synthesis of Biginelli-Type, Polyhydroquinoline and 2,3-Dihydroquinazolin-4(1H)-One Derivatives,” Journal of the Iranian Chemical Society 14 (2017): 121–34.
   Web of Science ®Google Scholar
• B. L. Li, A. G. Zhong, and A. G. Ying, “Novel SO3H-Functionalized Ionic Liquids—Catalyzed Facile and Efficient Synthesis of Polyhydroquinoline Derivatives via Hantzsch Condensation under Ultrasound Irradiation,” Journal of Heterocyclic Chemistry 52 (2014): 445–9.
   Web of Science ®Google Scholar
• A. Yaghoubi, M. G. Dekamin, and B. Karimi, “Propylsulfonic Acid-Anchored Isocyanurate-Based Periodic Mesoporous Organosilica (PMO-ICS-PrSO3H): A Highly Efficient and Recoverable Nanoporous Catalyst for the One-Pot Synthesis of Substituted Polyhydroquinolines,” Catalysis Letters 147 (2017): 2656–63.
   Web of Science ®Google Scholar
• S. M. Vahdat, M. A. Zolfigol, and S. Baghery, “Straightforward Hantzsch Four- and Three-Component Condensation in the Presence of Triphenyl(Propyl-3-Sulfonyl) Phosphoniumtrifluoromethanesulfonate {[TPPSP]OTf} as a Reusable and Green Mild Ionic Liquid Catalyst,” Applied Organometallic Chemistry 30 (2016): 311–7.
   Web of Science ®Google Scholar
• R. Surasani, D. Kalita, A.V. D. Rao, K. Yarbagi, and K. B. Chandrasekhar, “FeF3 as a Novel Catalyst for the Synthesis of Polyhydroquinoline Derivatives via Unsymmetrical Hantzsch Reaction,” Journal of Fluorine Chemistry 135 (2012): 91–6.
   Web of Science ®Google Scholar
• S. U. Tekale, V. P. Pagore, S. S. Kauthale, and R. P. Pawar, “La2O3/TFE: An Efficient System for Room Temperature Synthesis of Hantzsch Polyhydroquinolines,” Chinese Chemical Letters 25 (2014): 1149–52.
   Web of Science ®Google Scholar
• R. Pagadala, S. Maddila, V. D. B. C. Dasireddy, and S. B. Jonnalagadda “Zn-VCO3 Hydrotalcite: A Highly Efficient and Reusable Heterogeneous Catalyst for the Hantzsch Dihydropyridine Reaction,” Catalysis Communications 45 (2014): 148–52.
   Web of Science ®Google Scholar
• M. G. Sharma, D. P. Rajani, and H. M. Patel, “Electronic Supplementary Material from Green Approach for Synthesis of Bioactive Hantzsch 1,4-Dihydropyridine Derivatives Based on Thiophene Moiety via Multicomponent Reaction,” Royal Society Open Science 4 (2017): 170006–14.
   PubMed Web of Science ®Google Scholar
• G. Brahmachari and S. Laskar, “A Very Simple and Highly Efficient Procedure for N-Formylation of Primary and Secondary Amines at Room Temperature under Solvent-Free Conditions,” Tetrahedron Letters 51 (2010): 2319–22.
   Web of Science ®Google Scholar
• P. Wasserscheid, M. Sesing, and W. Korth, “Hydrogensulfate and Tetrakis (Hydrogensulfato) Borate Ionic Liquids: Synthesis and Catalytic Application in Highly Brønsted-Acidic Systems for Friedel–Crafts Alkylation,” Green Chemistry 4 (2002): 134–8.
   Web of Science ®Google Scholar
• H. R. Safaei, M. Safaei, and M. Shekouhy, “Sulfuric Acid-Modified Poly(Vinylpyrrolidone) ((PVP-SO3H)HSO4): A New Highly Efficient, Bio-Degradable and Reusable Polymeric Catalyst for the Synthesis of Acridinedione Derivatives,” RSC Advances 5 (2015): 6797–806.
   Web of Science ®Google Scholar
• O. Goli-Jolodar, F. Shirini, and M. Seddighi, “Introduction of O-Sulfonated Poly (Vinylpyrrolidonium) Hydrogen Sulfate as an Efficient, and Reusable Solid Acid Catalyst for Some Solvent-Free Multicomponent Reactions,” RSC Advances 6 (2016): 44794–806.
   Web of Science ®Google Scholar
• F. Shirini, A. Yahyazadeh, and K. Mohammadi, “A Solvent-Free Synthesis of Coumarins Using 1,3-Disulfonic Acid Imidazolium Hydrogen Sulfate as a Reusable and Effective Ionic Liquid Catalyst,” Research on Chemical Intermediates 41 (2015): 6207–18.
   Web of Science ®Google Scholar
• F. Shirini, P. N. Moghadam, S. Moayedi, and M. Seddighi, “Introduction of O-Sulfonated Poly (4-Vinylpyrrolidonium) Chloride as a Polymeric and Reusable Catalyst for the Synthesis of Xanthene Derivatives,” RSC Advances 4 (2014): 38581–8.
   Web of Science ®Google Scholar
• Mondal et al., “One-Pot Synthesis of Polyhydroquinoline Derivatives,” 1469–75.
   Google Scholar
• Li et al., “Novel SO3H-Functionalized Ionic Liquids,” 445–9.
   Google Scholar
• Yaghoubi et al., “Propylsulfonic Acid-Anchored Isocyanurate-Based Periodic Mesoporous Organosilica (PMO-ICS-PrSO3H),” 2656–63.
   Google Scholar
• Vahdat et al., “Straightforward Hantzsch Four- and Three-Component Condensation,” 311–7.
   Google Scholar
• Pagadala et al., “Zn-VCO3 Hydrotalcite,” 148–52.
   Google Scholar
• A. Zare, F. Abi, A. R. Moosavi-Zare, M. H. Beyzavi, and M. A. 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
• A. Khazaei, M. A. Zolfigol, A. R. Moosavi-Zare, J. Afsar, A. Zare, V. Khakyzadeh, and M. H. Beyzavi, “Synthesis of Hexahydroquinolines Using the New Ionic Liquid Sulfonic Acid Functionalized Pyridinium Chloride as a Catalyst,” Chinese Journal of Catalysis 34 (2013): 1936–44.
   Web of Science ®Google Scholar
• M. Tajbakhsh, H. Alinezhad, M. Norouzi, S. Baghery, and M. Akbari, “Protic Pyridinium Ionic Liquid as a Green and Highly Efficient Catalyst for the Synthesis of Polyhydroquinoline Derivatives via Hantzsch Condensation in Water,” Journal of Molecular Liquids 177 (2013): 44–8.
   Web of Science ®Google Scholar
• M. Abedini, F. Shirini, and M. Mousapour, “Poly (vinylpyrrolidinium) Perchlorate as a New and Efficient Catalyst for the Promotion of the Synthesis of Polyhydroquinoline Derivatives via Hantzsch Condensation,” Research on Chemical Intermediates 42 (2016): 2303–15.
   Web of Science ®Google Scholar
• S. Rostamnia and F. Pourhassan, “The SBA-15/SO3H Nanoreactor as a Highly Efficient and Reusable Catalyst for Diketene-Based, Four-Component Synthesis of Polyhydroquinolines and Dihydropyridines Under Neat Conditions,” Chinese Chemical Letters 24 (2013): 401–3.
   Web of Science ®Google Scholar
• M. Nasr-Esfahani, S. J. Hoseini, M. Montazerozohori, R. Mehrabi, and H. Nasrabadi, “Magnetic Fe3O4 Nanoparticles: Efficient and Recoverable Nanocatalyst for the Synthesis of Polyhydroquinolines and Hantzsch 1,4-Dihydropyridines under Solvent-Free Conditions,” Journal of Molecular Catalysis A: Chemical 382 (2014): 99–105.
   Web of Science ®Google Scholar
• R. Surasani, D. Kalita, A. D. Rao, K. Yarbagi, and K. Chandrasekhar, “FeF3 as a Novel Catalyst for the Synthesis of Polyhydroquinoline Derivatives via Unsymmetrical Hantzsch Reaction,” Journal of Fluorine Chemistry 135 (2012): 91–6.
   Web of Science ®Google Scholar
• B. Bandgar, P. More, V. Kamble, and J. Totre, “Synthesis of Polyhydroquinoline Derivatives under Aqueous Media,” ARKIVOC 15 (2008): 1–8.
   Web of Science ®Google Scholar
• S. Igder, A. R. Kiasat, and M. R. Shushizadeh, “Melamine Supported on Hydroxyapatite-Encapsulated-γ-Fe2O3: A Novel Superparamagnetic Recyclable Basic Nanocatalyst for the Synthesis of 1,4-Dihydropyridines and Polyhydroquinolines,” Research on Chemical Intermediates 41 (2015): 7227–44.
   Web of Science ®Google Scholar
• A. Maleki, M. Kamalzare, and M. Aghaei, “Efficient One-Pot Four-Component Synthesis of 1,4-Dihydropyridines Promoted by Magnetite/Chitosan as a Magnetically Recyclable Heterogeneous Nanocatalyst,” JNSC 5 (2015): 95–105.
   Google Scholar