Ultrasound-Promoted Regioselective Synthesis of Pyrazolyl-Bis Coumarinyl Methanes Using Citric Acid as a Natural and Efficient Catalyst

References

• F. Borges, F. Roleira, N. Milhazes, L. Santana, and E. Uriarte, “Simple Coumarins and Analogues in Medicinal Chemistry: Occurrence, Synthesis, and Biological Activity,” Current Medicinal Chemistry 12 (2005): 887–916.
   PubMed Web of Science ®Google Scholar
• A. Bolognese, G. Correale, M. Manfra, A. Levecchia, O. Mazzoni, E. Novellino, P. Lacolla, 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 (2004): 849–58.
   PubMed Web of Science ®Google Scholar
• 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 Multhaup,” Clinical Neuropathology 25 (2006): 163–71.
   PubMed Web of Science ®Google Scholar
• A. Lacy and R.O. Kennedy, “Studies on Coumarins and Coumarin-Related Compounds to Determine their Therapeutic Role in the Treatment of Cancer,” Current Pharmaceutical Design 10 (2004): 3797–811.
   PubMed Web of Science ®Google Scholar
• W.O. Foye, Principidi Chimica Farmaceutica Piccin- Padova (1991) Italy.
   Google Scholar
• C.X. Su, J.F. Mouscadet, C.C. Chiang, H.J. Tsai, and L.Y. Hsu, “HIV-1 Integrase Inhibition of Biscoumarin Analogues,” Chemical and Pharmaceutical Bulletin 54 (2006): 682–6.
   PubMed Web of Science ®Google Scholar
• B.M. Trost, “Atom Economy-A Challenge for Organic Synthesis: Homogeneous Catalysis Leads the Way,” Angewandte Chemie International Edition in English 34 (1995): 259–81.
   Web of Science ®Google Scholar
• 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 (2014): 535–40.
   Web of Science ®Google Scholar
• M.I. Choudhary, N. Fatima, K.M. Khan, S. Jalil, S. Iqbal, and R. Atta-ur, “New Biscoumarin Derivatives-Cytotoxicity and Enzyme Inhibitory Activities,” Bioorganic & Medicinal Chemistry 14 (2006): 8066–72.
   PubMed Web of Science ®Google Scholar
• G.P. Ellis, “The Chemistry of Heterocyclic Compounds,” in Chromenes, Chromenes, and chromenes, edited by A. Weissberger and E. C. Taylor, Chapter 2 (New York: John Wiley, 1977), 11.
   Google Scholar
• M.A. Zolfigol, A.R. Mousavi-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 (2014): 1264–7.
   Web of Science ®Google Scholar
• J.M. Khurana and S. Kumar, “Ionic Liquid: An Efficient and Recyclable Medium for the Synthesis of Octahydroquinazolinone and Biscoumarin Derivatives,” Monatshefte Fur Chemie 141 (2010): 561–4.
   Web of Science ®Google Scholar
• 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 (2011): 122–7.
   Web of Science ®Google Scholar
• K.M. Khan, S. Iqbal, M.A. Lodhi, G.M. Maharvi, Mhary. Zia-Ullah, Atta-ur-Rahman, and S. Perveen, “Biscoumarin: New Class of Urease Inhibitors; Economical Synthesis and Activity,” Bioorganic & Medicinal Chemistry 12 (2004): 1963–8.
   PubMed Web of Science ®Google Scholar
• H. Hagiwara, S. Miya, T. Suzuki, M. Ando, I. Yamamoto, and M. Kato, “Et2AlCl Promoted Coupling Reactions of 4-Hydroxy-2-Pyrone or 4-Hydroxycoumarine with Aldehydes: Synthesis of Methylenebis-(4-Hydroxy-2-Pyrone) or Methylenebis-(4-Hydroxycoumarine) Derivatives,” Heterocycles 51 (1999): 493–6.
   Web of Science ®Google Scholar
• K. Tabatabaeian, H. Heidari, A. Khorshidi, M. mamaghani, and N.O. Mahmoodi, “Synthesis of Biscoumarin Derivatives by the Reaction of Aldehydes and 4-Hydroxycoumarin Using Ruthenium(III) Chloride Hydrate as a Versatile Homogeneous Catalyst,” Journal of the Serbian Chemical Society 77 (2012): 407–13.
   Web of Science ®Google Scholar
• 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 sSlvent-Free Conditions,” Tetrahedron Letters 50 (2009): 4125–7.
   Web of Science ®Google Scholar
• V. Padalkar, K. Phatangare, S. Takale, R. Pisal, and A. Chaskar, “Silica Supported Sodium Hydrogen Sulfate and Indion 190 Resin: An Efficient and Heterogeneous Catalyst for Facile Synthesis of Bis-(4-Hydroxycoumarin-3-Yl) Methanes,” Journal of Saudi Chemical Society 19 (2015): 42–5.
   Web of Science ®Google Scholar
• H. Mehrabi and H. Abusaidi, “Synthesis of Biscoumarin and 3,4-Dihydropyrano[c]Chromene Derivatives CatalyZed by Sodium Dodecyl Sulfate (SDS) in Neat Water,” Journal of the Iranian Chemical Society 7 (2010) 890–4.
   Web of Science ®Google Scholar
• U.N. Yadav and G.S. Shankarling, “Room Temperature Ionic Liquid Choline Chloride–Oxalic Acid: A Versatile Catalyst for Acid-Catalyzed Transformation in Organic Reactions,” Journal of Molecular Liquids 191 (2014) 137–41.
   Web of Science ®Google Scholar
• W. Li, Y. Wang, Z. Wang, L. Dai, and Y. Wang, “Novel SO3H-Functionalized Ionic Liquids Based on Benzimidazolium Cation: Efficient and Recyclable Catalysts for One-Pot Synthesis Of Biscoumarin Derivatives,” Catalysis Letters 141 (2011): 1651–8.
   Web of Science ®Google Scholar
• J.T. Li, Y. Yin, and M.X. Sun, “An Efficient One-Pot Synthesis of 2,3-Epoxyl-1,3-Diaryl-1-Propanone Directly from Acetophenones and Aromatic Aldehydes Under Ultrasound Irradiation,” Ultrasonics Sonochemistry 17 (2010): 363–6.
   PubMed Web of Science ®Google Scholar
• M. Shekouhy and A. Hasaninejad, “Ultrasound-Promoted Catalyst-Free One-Pot Four Component Synthesis of 2H-Indazolo[2,1-b]Phthalazine-Triones in Neutral Ionic Liquid 1-butyl-3-Methylimidazolium Bromide,” Ultrasonics Sonochemistry 19 (2012): 307–13.
   PubMed Web of Science ®Google Scholar
• R. Cella and S. H. , “Ultrasound in Heterocycles Chemistry,” Tetrahedron 65 (2009): 2619–41.
   Web of Science ®Google Scholar
• E. Ramu, V. Kotra, N. Bansal, R. Varala, and S.R. Adapa, “Green Approach for the Efficient Synthesis of Biginilli Compounds Promoted by Citric Acid Under Solvent Free Condition,” Rasayan Journal of Chemistry 1 (2008): 188–94.
   Google Scholar
• Q.S. Ding, J.L. Zhang, J.X. Chen, M.C. Liu, J.C. Ding, and H.Y. Wu, “Tandem Synthesis of 2,3-Dihydroquinazolin-4(1H)-Ones on Grinding Under Solvent-Free Conditions,” Journal of Heterocyclic Chemistry 49 (2012): 375–80.
   Web of Science ®Google Scholar
• S. Sajjadifar, M.A. Zolfigol, G.A. Chehardoli, S. Miri, and P. Moosavi, “Qinoxaline II. A Practical Efficient and Rapid Synthesis of New Quinoxalines Catalyzed by Citric Acid as a Trifunctional Bronsted Acid at Room Temperature Under Green Condition,” International Journal of Chem Tech Research 5 (2013): 422–9.
   Google Scholar
• M.Z. Ahmed, N.T. Patel, K.A. Shaikh, M.A. Baseer, S. Shaikh, and V.A. Patti, “Atom Efficient Grinding Technique for the Synthesis of Hydrazones Catalyzed by Citric Acid,” Elixier Organic Chemistry 43 (2010): 6583–5.
   Google Scholar
• L. Zare Fekri, M. Nikpassand, and K. Hasanpour, “Green Aqueous Synthesis of Mono, Bis and Trisdihydropyridines Using Nano Fe3O4 Under Ultrasound Irradiation,” Current Organic Synthesis 12 (2015): 76–9.
   Web of Science ®Google Scholar
• L. Zare Fekri, M. Nikpassand, and R. Maleki, “1, 4-Diazabicyclo [2.2. 2] Octanium Diacetate: As an Effective, New and Reusable Catalyst for the Synthesis of Benzo [d] Imidazole,” Journal of Molecular Liquids 222 (2016): 77–81.
   Web of Science ®Google Scholar
• M. Nikpassand, M. Mamaghani, F. Shirini, and K. Tabatabaeian, “A Convenient Ultrasound-Promoted Regioselective Synthesis of Fused Polycyclic 4-Aryl-3-Methyl-4,7-Dihydro-1H-Pyrazolo[3,4-b]Pyridines,” Ultrasonics Sonochemistry 17 (2010): 301–5.
   PubMed Web of Science ®Google Scholar
• M. Nikpassand, L. Zare Fekri, L. Karimian, and M. Rassa, “Synthesis of Biscoumarin Derivatives Using Nanoparticle Fe3O4 as an Efficient Reusable Heterogeneous Catalyst in Aqueous Media and their Antimicrobial Activity,” Current Organic Synthesis 12 (2015): 358–62.
   Web of Science ®Google Scholar
• M. Nikpassand, L. Zare Fekri, and P. Farokhian, “An Efficient and Green Synthesis of Novel Benzoxazole Under Ultrasound Irradiation,” Ultrasonics Sonochemistry 28 (2016): 341–5.
   PubMed Web of Science ®Google Scholar
• R.M. Srivastava, R.A.W.N. Filho, C.A. Silva, and A. Bortoluzzi, “First Ultrasound-Mediated One-Pot Synthesis of N-Substituted Amides,” Ultrasonics Sonochemistry 16 (2009): 737–42.
   PubMed Web of Science ®Google Scholar
• H.A. Stefani, C.M.P. Pereira, R.B. Almeida, R.C. Braga, K.P. Guzenb, and R. Cella, “A Mild and Efficient Method for Halogenation of 3,5-Dimethyl Pyrazoles by Ultrasound Irradiation Using N-Halosuccinimides,” Tetrahedron Letters 46 (2005): 6833–7.
   Web of Science ®Google Scholar
• A. Duarte, W. Cunico, C.M.P. Pereira, A.F.C. Flores, R.A. Freitag, and G.M. Siqueira, “Ultrasound Promoted Synthesis of Thioesters from 2-Mercaptobenzoxa(Thia)Zoles,” Ultrasonics Sonochemistry 17 (2010): 281–3.
   PubMed Web of Science ®Google Scholar