450
Views
31
CrossRef citations to date
0
Altmetric
Research Articles

Synthesis of Pyran-Annulated Heterocyclic Systems Catalyzed by Theophylline as a Green and Bio-Based Catalyst

Pages 160-172 | Received 20 Aug 2018, Accepted 18 Jan 2019, Published online: 11 May 2019

References

  • N. Foloppe, L. M. Fisher, R. Howes, A. Potter, A. G. S. Robertson, and A. E. Surgenor, “Identification of Chemically Diverse Chk1 Inhibitors by Receptor-Based Virtual Screening,” Bioorganic & Medicinal Chemistry 14, (2006): 4792–802.
  • S. C. Kuo, L. J. Huang, and H. Nakamura, “Studies on Heterocyclic Compounds. 6. Synthesis and Analgesic and Antiinflammatory Activities of 3, 4-Dimethylpyrano[2,3-c]pyrazol-6-one Derivatives,” Journal of Medicinal Chemistry 27, no. 4 (1984): 539–44.
  • J.-L. Wang, D. Liu, Z.-J. Zhang, S. Shan, X. Han, S. M. Srinivasula, C. M. Croce, E. S. Alnemri, and Z. 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.
  • V. K. Ahluwalia, A. Dahiya, and V. Garg, “Reaction of 5-Amino-4-formyl-3-methyl (or Phenyl)-1-phenyl-1H-pyrazoles with Active Methylene Compounds: Synthesis of Fused Heterocyclic Rings,” Indian Journal of Biochemistry and Biophysics 36, (1997): 88–90.
  • G. P. Ellis, “The Chemistry of Heterocyclic Compounds,” in Chromenes, Chromenes, and Chromenes, ed A. Weissberger, and E. C. Taylor (New York: John Wiley, 1977), 13.
  • D. Heber, C. Heers, and U. Ravens, “Positive Inotropic Activity of 5-Amino-6-cyano-1,3-dimethyl-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidine-2,4-dione in Cardiac Muscle from Guinea-Pig and Man. Part 6: Compounds with Positive Inotropic Activity,” Pharmazie 48, (1993): 537–41.
  • W. J. Coates, “Pyrimidopyrimidine Derivatives,” European Patent 351058, Chemical Abstracts 113, (1990): 40711.
  • N. Fokialakis, P. Magiatis, I. Chinou, S. Mitaku, and F. Tillequin, “Megistoquinones I and II, Two Quinoline Alkaloids with Antibacterial Activity from the Bark of Sarcomelicope Megistophylla,” Chemical and Pharmaceutical Bulletin 50, no. 3 (2002): 413–4.
  • P. Beagley, M. A. L. Blackie, K. Chibale, C. Clarkson, R. Meijboom, J. R. Moss, P. Smith, and H. Su, “Synthesis and Antiplasmodial Activity In Vitro of New Ferrocene–Chloroquine Analogues,” Dalton Transactions no. 15 (2003): 3046–51.
  • J. G. Cannon, P. R. Khonje, and J. P. Long, “Centrally Acting Emetics. 9. Hofmann and Emde Degradation Products of Nuciferine,” Journal of Medicinal Chemistry 18, no. 1 (1975): 110–2.
  • C. Biot, G. Glorian, L. A. Maciejewski, J. S. Brocard, O. Domarle, G. Blampain, G. Blampain, P. Blampain, A. J. Georges, H. Abessolo, et al., “Synthesis and Antimalarial Activity In Vitro and In Vivo of a New Ferrocene-Chloroquine Analogue,” Journal of Medicinal Chemistry 40, (1997): 3715–8.
  • E. A. A. Hafez, M. H. Elnagdi, A. G. A. Elagamey, and F. M. A. A. EL-Taweel, “Triles in Heterocyclic Synthesis: Novel Synsthesis of Benzo[c]-Coumarin and of Benzo[c]pyrano[3,2-c]quinoline Derivatives,” Heterocycles 26, (1987): 903–7.
  • T. A. Bayer, S. Schafer, H. Breyh, O. Breyhan, C. Wirths, and G. A. Treiber, “A Vicious Circle: Role of Oxidative Stress, Intraneuronal Aβ and Cu in Alzheimer’s Disease,” Clinical Neuropathology 25, (2006): 163–71.
  • M. A. Bodaghifard, M. Solimannejad, S. Asadbegi, and S. Dolatabadifarahani, “Mild and Green Synthesis of Tetrahydrobenzopyran, Pyranopyrimidinone and Polyhydroquinoline Derivatives and DFT Study on Product Structures,” Research on Chemical Intermediates 42, no. 2 (2016): 1165–79.
  • S. Banerjee, A. Horn, H. Khatri, and G. Sereda, “A Green One-Pot Multicomponent Synthesis of 4H-pyrans and Polysubstituted Aniline Derivatives of Biological, Pharmacological, and Optical Applications Using Silica Nanoparticles as Reusable Catalyst,” Tetrahedron Letters 52, no. 16 (2011): 1878–81.
  • 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.
  • K. Niknam, N. Borazjani, R. Rashidian, and A. Jamali, “Silica-Bonded N-Propylpiperazine Sodium n-Propionate as Recyclable Catalyst for Synthesis of 4H-Pyran Derivatives,” Chinese Journal of Catalysis 34, no. 12 (2013): 2245–54.
  • E. Sheikhhosseini, D. Ghazanfari, and V. Nezamabadi, “A New Method for Synthesis of Tetrahydrobenzo [b] pyrans and Dihydropyrano[c]chromenes Using p-Dodecylbenzenesulfonic Acid as Catalyst in Water,” Iranian Journal of Catalysis 3, (2013): 197–201.
  • A. A. Mohammadi, M. R. Asghariganjeh, and A. Hadadzahmatkesh, “Synthesis of Tetrahydrobenzo [b] pyran under Catalysis of NH4Al (SO4)2·12H2O (Alum),” Arabian Journal of Chemistry 10, (2017): S2213–S6.
  • B. Maleki and S. Sedigh 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.
  • M. A. Zolfigol, M. Safaiee, and N. Bahrami-Nejad, “Dendrimeric Magnetic Nanoparticle Cores with Co-Phthalocyanine Tags and Their Application in the Synthesis of Tetrahydrobenzo [b] pyran Derivatives,” New Journal of Chemistry 40, no. 6 (2016): 5071–9.
  • S. Banerjee, and A. Saha, “Free-ZnO Nanoparticles: A Mild, Efficient and Reusable Catalyst for the One-Pot Multicomponent Synthesis of Tetrahydrobenzo[b]pyran and Dihydropyrimidone Derivatives,” New Journal of Chemistry 37, (2013): 4170–5.
  • M. Esmaeilpour, J. Javidi, F. Dehghani, and F. Nowroozi Dodeji, “A Green One-Pot Three-Component Synthesis of Tetrahydrobenzo[b]pyran and 3,4-Dihydropyrano[c]chromene Derivatives Using a Fe3O4@SiO2–imid–PMAn Magnetic Nanocatalyst under Ultrasonic Irradiation or Reflux Conditions,” RSC Advances 5, no. 34 (2015): 26625–33.
  • B. Maleki, H. Eshghi, M. Barghamadi, N. Nasiri, A. Khojastehnezhad, S. Sedigh Ashrafi, and O. Pourshiani, “Silica-Coated Magnetic NiFe2O4 Nanoparticles Supported H3PW12O40; Synthesis, Preparation, and Application as an Efficient, Magnetic, Green Catalyst for One-Pot Synthesis of Tetrahydrobenzo[b]pyran and Pyrano[2,3-c]pyrazole Derivatives,” Research on Chemical Intermediates 42, no. 4 (2016): 3071–93.
  • N. Seyyedi, F. Shirini, M. Safarpoor, and N. Langarudi, “DABCO-Based Ionic Liquids: Green and Recyclable Catalysts for the Synthesis of Barbituric and Thiobarbituric Acid Derivatives in Aqueous Media,” RSC Advances 6, no. 50 (2016): 44630–40.
  • M. Bararjanian, S. Balalaie, B. Movassag, and A. M. Amani, “One-Pot Synthesis of Pyrano[2,3-d]pyrimidinone Derivatives Catalyzed by L-Proline in Aqueous Media,” Journal of the Iranian Chemical Society 6, no. 2 (2009): 436–42.
  • E. Sheihhosseini, T. Sattaei Mokhatari, M. Faryabi, A. Rafiepour, and S. Soltaninejad, “Iron Ore Pellet, A Natural and Reusable Catalyst for Synthesis of Pyrano[2,3-d]pyrimidine and Dihydropyrano[c]chromene Derivatives in Aqueous Media,” Iranian Journal of Chemistry and Chemical Engineering 35, (2016): 43–50.
  • B. Sadeghi, M. Bouslik, and M. R. Shishehbore, “Nano-Sawdust-OSO3H as a New, Cheap and Effective Nanocatalyst for One-Pot Synthesis of Pyrano[2,3-d]pyrimidines,” Journal of the Iranian Chemical Society 12, no. 10 (2015): 1801–8.
  • B. Sabour, M. Hassan Peyrovi, and M. Hajimohammadi, “Al-HMS-20 Catalyzed Synthesis of Pyrano[2,3-d]pyrimidines and Pyrido[2,3-d]pyrimidines via Three-component Reaction,” Research on Chemical Intermediates 41, no. 3 (2015): 1343–50.
  • A. Khazaei, H. A. Alavi 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.
  • S. N. Maddila, S. Maddila, W. E. van Zyl, and S. B. Jonnalagadda, “Mn Doped ZrO2 as a Green, efficient and Reusable Heterogeneous Catalyst for the Multicomponent Synthesis of Pyrano[2,3-d]-Pyrimidine Derivatives,” RSC Advances 5, no. 47 (2015): 37360–6.
  • 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.
  • 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.
  • A. Saha, S. Payra, and S. Banerjee, “One-pot Multicomponent Synthesis of Highly Functionalized Bio-active Pyrano[2,3-c]pyrazole and Benzylpyrazolyl Coumarin Derivatives Using ZrO2 Nanoparticles as a Reusable Catalyst,” Green Chemistry 17, no. 5 (2015): 2859–66.
  • A. Moshtaghi Zonouz, and D. Moghani, “Green and Highly Efficient Synthesis of Pyranopyrazoles in Choline Chloride/Urea Deep Eutectic Solvent,” Synthetic Communications 46, no. 3 (2016): 220–5.
  • M. A. Zolfigol, M. Tavasoli, A. R. Moosavi-Zare, P. Moosavi, H. G. Kruger, M. Shiri, and V. Khakyzadeh, “Synthesis of Pyranopyrazoles Using Isonicotinic Acid as a Dual and Biological Organocatalyst,” RSC Advances 3, no. 48 (2013): 25681–5.
  • J. B. Gujar, M. A. Chaudhari, D. S. Kawade, and M. S. Shingare, “Molecular Sieves: An Efficient and Reusable Catalyst for Multi-component Synthesis of Dihydropyrano[2,3-C]pyrazole Derivatives,” Tetrahedron Letters 55, no. 44 (2014): 6030–3.
  • R.-Y. Guo, Z.-M. An, L.-P. Mo, S.-T. Yang, H.-X. Liu, S.-X. Wang, and Z.-H. Zhang, “Meglumine Promoted One-Pot, Four-Component Synthesis of Pyranopyrazole Derivatives,” Tetrahedron 69, no. 47 (2013): 9931–8.
  • F. Tamaddon, and M. Alizadeh, “A Four-Component Synthesis of Dihydropyrano[2,3-c]pyrazoles in a New Water-Based Worm-Like Micellar Medium,” Tetrahedron Letters 55, no. 26 (2014): 3588–91.
  • H. Mecadon, M. R. Rohman, I. Kharbangar, B. M. Laloo, I. Kharkongor, M. Rajbangshi, and B. Myrboh, “L-Proline as an Efficicent Catalyst for the Multi-Component Synthesis of 6-Amino-4-alkyl/aryl-3-methyl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitriles in Water,” Tetrahedron Letters 52, no. 25 (2011): 3228–31.
  • M. Wu, Q. Feng, D. Wan, and J. Ma, “CTACl as Catalyst for Four-component, One-Pot Synthesis of Pyranopyrazole Derivatives in Aqueous Medium,” Synthetic Communications 43, no. 12 (2013): 1721–6.
  • P. P. Bora, M. Bihani, and G. Bez, “Multicomponent Synthesis of Dihydropyrano[2,3-c]pyrazoles Catalyzed by Lipase from Aspergillus niger,” Journal of Molecular Catalysis B: Enzymatic 92, (2013): 24–33.
  • Y. A. Tayade, S. A. Padvi, Y. B. Wagh, and D. S. Dalal, “βCyclodextrin as a Supramolecular Catalyst for the Synthesis of Dihydropyrano [2,3-c]pyrazole and Spiro[indoline-3,4’-pyrano[2,3-c]pyrazole] in Aqueous Medium,” Tetrahedron Letters 56, no. 19 (2015): 2441–7.
  • P. T. Anastas, and J. B. Zimmerman, “Peer Reviewed: Design through the 12 Principles of Green Engineering,” Environmental Science & Technology 37, (2003): 94A–101A.
  • G. T. Pawar, R. R. Magar, and M. K. Lande, “Mesolite: An Efficient Heterogeneous Catalyst for One-Pot Synthesis of 2-Amino-4H-Chromenes,” Polycyclic Aromatic Compounds 38, no. 1 (2018): 75–84.
  • Q. Zhao, C.-S. Yao, and X.-S. Wang, “One-Pot Four-Component Synthesis of 5,10-Diarylpyrido[4,3-b][1,6] Naphthyridine Derivatives in Ionic Liquids Catalyzed by TsOH,” Polycyclic Aromatic Compounds 38, no. 3 (2018): 236–43.
  • S. B. Abd Hamid, S. J. J. Titinchi, H. Abbo, and N. Ghaffari Khaligh, “One-Pot Multicomponent Synthesis of Pyrazolo[3,4-d]pyrimidine-6-one Derivatives,” Polycyclic Aromatic Compounds 38, (2018): 189–98.
  • S. Behravesh, R. Fareghi-Alamdari, and R. Badri, “Sulfonated Reduced Graphene Oxide (RGO-SO3H): As an Efficient Nanocatalyst for One-Pot Synthesis of 2-Amino-3-cyano-7-hydroxy-4H-chromenes Derivatives in Water,” Polycyclic Aromatic Compounds 38, no. 1 (2018): 51–65.
  • B. M. Trost, “Atom Economy—A Challenge for Organic Synthesis: Homogeneous Catalysis Leads the Way,” Angewandte Chemie International Edition in English 34, no. 3 (1995): 259–81.
  • B. B. Tour, and D. G. Hall, “Natural Product Synthesis Using Multicomponent Reaction Strategies,” Chemical Reviews 109, (2009): 4439–86.
  • F. Mohamadpour, “One-Pot Access to Polyfunctionalized Piperidine Scaffolds via Glutamic Acid Catalyzed Knoevenagel–Intramolecular [4 + 2] aza-Diels-Alder Imin-Based Multi-Component Reaction under Ambient Temperature,” Polycyclic Aromatic Compounds (2018).
  • F. Mohamadpour, and M. Lashkari, “Three-Component Reaction of β-Keto Esters, Aromatic Aldehydes and Urea/Thiourea Promoted by Caffeine, a Green and Natural, Biodegradable Catalyst for Eco-Safe Biginelli Synthesis of 3,4-Dihydropyrimidin-2(1H)-Ones/Thiones Derivatives under Solvent-Free Conditions,” Journal of the Serbian Chemical Society 83, (2018): 673–84.
  • F. Mohamadpour, M. Lashkari, M. T. Maghsoodlou, and R. Heydari, “Phthalic Acid: A Green, Biodegradable and Environmentally Benign Nature Difunctional Brønsted Acid Catalyst for the One-POT Synthesis of 3,4-Dihydropyrimidin-2-(1H)-One Derivatives and Substituted Dihydro-2-Oxypyrroles,” Journal of the Chilean Chemical Society 63, no. 1 (2018): 3811–8.
  • F. Mohamadpour, M. T. Maghsoodlou, R. Heydari, and M. Lashkari, “Saccharin: A Green, economical and Efficient Catalyst for the One-Pot, Multi-Component Synthesis of 3,4-Dihydropyrimidin-2-(1H)-One Derivatives and 1H-Pyrazolo[1,2-b]phthalazine-5,10-dione Derivatives and Substituted Dihydro-2-Oxypyrrole,” Journal of the Iranian Chemical Society 13, no. 8 (2016): 1549–60.
  • F. Mohamadpour, M. T. Maghsoodlou, R. Heydari, and M. Lashkari, “Tartaric Acid: A Naturally Green and Efficient Di-Functional Brønsted Acid Catalyst for the One-Pot Four-Component Synthesis of Polysubstituted Dihydropyrrol-2-Ones at Ambient Temperature,” Iranian Journal of Science and Technology, Transactions A: Science 41, no. 3 (2017): 843–9.
  • J. W. Daly, “Caffeine Analogs: Biomedical Impact,” Cellular and Molecular Life Sciences 64, no. 16 (2007): 2153–69.
  • L. Maia, and A. de Mendonca, “Does Caffeine Intake Protect from Alzheimer’s Disease?,” European Journal of Neurology 9, no. 4 (2002): 377–82.
  • R. J. Stine, R. H. Marcus, and C. A. Parvin, “Aminophylline Loading in Asthmatic Patients: A Protocol Trial,” Annals of Emergency Medicine 18, no. 6 (1989): 640.
  • P. Cui, T. L. Macdonald, M. Chen, and J. L. Nadler, “Synthesis and Biological Evaluation of Lisofylline (LSF) analogs as a Potential Treatment for Type 1 Diabetes,” Bioorganic & Medicinal Chemistry Letters 16, (2006): 3401–5.
  • B. Song, T. Xiao, X. Qi, L.-N. Li, K. Qin, S. Nian, G.-X. Hu, Y. f Yu, G. Liang, and F. Ye, “Design and Synthesis of 8-Substituted Benzamidophen Ylxanthine Derivatives as MAO-B Inhibitors,” Bioorganic & Medicinal Chemistry Letters 22, (2012): 1739–42.
  • A. C. Roy, F. A. Lunn, and S. L. Bearne, “Inhibition of CTP Synthase from Escherichia coli by Xanthines and Uric Acids,” Bioorganic & Medicinal Chemistry Letters 20, (2010): 141–4.
  • A. J. Szentmiklosi, A. Cseppento, R. Gesztelyi, J. Zsuga, Á. Körtvély, G. Harmati, and P. P. Nánási, “Xanthine Derivatives in the Heart: Blessed or Cursed?,” Current Medicinal Chemistry 18, no. 24 (2011): 3695–706.
  • D. Wang, S. P. Hong, and K. H. Row, “Solid Extraction of Caffeine and Theophylline from Green Tea by Molecular Imprinted Polymers,” Korean Journal of Chemical Engineering 21, no. 4 (2004): 853–7.
  • K. Rathore, R. Vyrs, and G. L. Talesara, “Synthesis and Antibacterial Evaluation of Some Theophylline Derivatives,” Indian Journal of Chemistry 44B, (2005): 2166–70.
  • A. Yazdani-Elah-Abadi, M. T. Maghsoodlou, R. Mohebat, and R. Heydari, “Theophylline as a New and Green Catalyst for the One-Pot Synthesis of Spiro[benzo[a]pyrano[2,3-c]phenazine] and Benzo[a]pyrano[2,3-c] phenazine Derivatives under Solvent-Free Conditions,” Chinese Chemical Letters 28, no. 2 (2017): 446–52.

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.