104
Views
5
CrossRef citations to date
0
Altmetric
Research Articles

Introduction of Agar-Entrapping as a Novel Strategy to Improve the Catalytic Activity of Moisture-Absorbing Acidic Ionic Liquids: A Case Study in the Synthesis of 5-Arylidene Barbituric Acids and Pyrano[2,3-d]Pyrimidinones

, ORCID Icon &
Pages 2471-2482 | Received 06 May 2020, Accepted 07 Oct 2020, Published online: 04 Nov 2020

References

  • R. R. Hawker, R. S. Haines, and J. B. Harper, “The Effect of Varying the Anion of an Ionic Liquid on the Solvent Effects on a Nucleophilic Aromatic Substitution Reaction,” Organic & Biomolecular Chemistry 16, no. 18 (2018): 3453–63.
  • F. Shirini, M. S. N. Langarudi, M. Seddighi, and O. G. Jolodar, “Bi-SO3H Functionalized Ionic Liquid Based on DABCO as a Mild and Efficient Catalyst for the Synthesis of 1,8- Dioxo-Octahydro-Xanthene and 5-Arylmethylenepyrimidine-2,4,6-Trione Derivatives,” Research on Chemical Intermediates 41, no. 11 (2015): 8483–97.
  • N. Seyyedi, F. Shirini, and M. S. 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.
  • F. Shirini, M. S. N. Langarudi, and N. Daneshvar, “Preparation of a New DABCO-Based Ionic Liquid [H2-DABCO][H2PO4]2} and Its Application in the Synthesis of Tetrahydrobenzo[b]Pyran and Pyrano[2,3-d]Pyrimidinone Derivatives,” Journal of Molecular Liquids 234 (2017): 268–78.
  • F. Shirini, M. S. N. Langarudi, N. Daneshvar, M. Mashhadinezhad, and N. Nabinia, “Preparation of a New DABCO-Based Ionic Liquid and Investigation on Its Application in the Synthesis of Benzimidazoquinazolinone and Pyrimido[4,5-b]-Quinoline Derivatives,” Journal of Molecular Liquids 243 (2017): 302–12.
  • F. Shirini, M.S.N. Langarudi, N. Daneshvar, N. Jamasbi, M. Irankhah-Khanghah, “Preparation and characterization of [H2-DABCO][ClO4]2 as a new member of DABCO-based ionic liquids for the synthesis of pyrimido[4,5-b]-quinoline and pyrimido[4,5-d]pyrimidine derivatives,” Journal of Molecular Structure 1161 (2018): 366–382.
  • N. Jamasbi, M. Irankhah-Khanghah, F. Shirini, H. Tajik, and M. S. N. Langarudi, “DABCO-Based Ionic Liquids: introduction of Two Metal-Free Catalysts for One-Pot Synthesis of 1,2,4-Triazolo[4,3-a]Pyrimidines and Pyrido[2,3-d]Pyrimidines,” New Journal of Chemistry 42, no. 11 (2018): 9016–27.
  • N. Daneshvar, O. Goli-Jolodar, R. Karimi-Chayjani, M. S. N. Langarudi, and F. Shirini, “Sustainable and Eco-Friendly Method for the Synthesis of Some Bioactive Derivatives of Biscoumarin and Pyrano [3,2-c]Chromene-3-Carbonitrile Using Taurine, as the Catalyst,” ChemistrySelect 4, no. 5 (2019): 1562–6.
  • N. Daneshvar, F. Shirini, M. S. N. Langarudi, and R. Karimi-Chayjani, “Taurine as a Green Bio-Organic Catalyst for the Preparation of Bio-Active Barbituric and Thiobarbituric Acid Derivatives in Water Media,” Bioorganic Chemistry 77 (2018): 68–73.
  • N. Kitamura, A. Onishi, (European Patent, 163599, 1984, Chemical Abstracts 1984, 104, 186439).
  • S. Furuya, and T. Ohtaki, “Pyridopyrimidine Derivatives, Their Production and Use” (European Patent Application, EP 608565, 1994, Chemical Abstracts 1994, 121, 205395w).
  • 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, 1990, 113, 40711).
  • Y. Sakuma, M. Hasegawa, K. Kataoka, K. Hoshina, N. Yamazaki, T. Kadota, and H. Yamaguchi, “1,10-Phenanthroline Derivatives” (WO 91/05785 PCT Int. Appl., 1989. Chem. Abstr., 1991, 115, 71646).
  • A. D. Broom, J. L. Shim, and G. L. Anderson, “Pyrido(2,3-d)pyrimidines. IV. Synthetic studies leading to various oxopyrido(2,3-d)pyrimidines,” The Journal of Organic Chemistry 41, no. 7 (1976): 1095–9.
  • 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.
  • E. Sheikhhosseini, T. S. Mokhtari, M. Faryabi, A. Rafiepour, and Sh 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.
  • C. Wang, J. J. Ma, X. Zhou, X. H. Zang, Z. Wang, Y. J. Gao, and P. L. Cui, “1‐n‐Butyl‐3‐Methylimmidazolium Tetrafluoroborate–Promoted Green Synthesis of 5‐Arylidene Barbituric Acids and Thiobarbituric Acid Derivatives,” Synthetic Communications 21 (2005): 2759–64.
  • R. Pourhasan‐Kisomi, F. Shirini, and M. Golshekan, “Introduction of Organic/Inorganic Fe3O4@MCM‐41@Zr‐Piperazine Magnetite Nanocatalyst for the Promotion of the Synthesis of Tetrahydro‐4H‐Chromene and Pyrano[2,3‐d]Pyrimidinone Derivatives,” Applied Organometallic Chemistry 32 (2018): e4371.
  • M. A. Zolfigol, R. Ayazi-Nasrabadi, and S. Baghery, “The First Urea-Based Ionic Liquid-Stabilized Magnetic Nanoparticles: An Efficient Catalyst for the Synthesis of Bis(Indolyl)Methanes and Pyrano[2,3-d]Pyrimidinone Derivatives,” Applied Organometallic Chemistry 30, no. 5 (2016): 273–81.
  • S. S. Shinde, G. Rashinkar, and R. Salunkhe, “DABCO Entrapped in Agar-Agar: A Heterogeneous Gelly Catalyst for Multi-Component Synthesis of 2-Amino-4H-Chromenes,” Journal of Molecular Liquids 178 (2013): 122–6.
  • J. T. Li, H. G. Dai, D. Liu, and T. S. Li, “Efficient Method for Synthesis of the Derivatives of 5‐Arylidene Barbituric Acid Catalyzed by Aminosulfonic Acid with Grinding,” Synthetic Communications 36, no. 6 (2006): 789–94.
  • J. M. Khurana, and K. Vij, “Nickel Nanoparticles Catalyzed Knoevenagel Condensation of Aromatic Aldehydes with Barbituric Acids and 2-Thiobarbituric Acids,” Catalysis Letters 138, no. 1–2 (2010): 104–10.
  • S. Kamble, G. Rashinkar, A. Kumbhar, K. Mote, and R. Salunkhe, “Green Chemistry Approach for Synthesis of 5-Arylidine Barbituric Acid Derivatives by Hydrotrope Induced Knovenagel Condensation in Aqueous Medium,” Archives of Applied Science Research 2 (2010): 217–22.
  • S. B. Rathod, A. B. Gambhire, B. R. Arbad, and M. K. Lande, “Synthesis, Characterization and Catalytic Activity of Ce1MgxZr1-xO2(CMZO) Solid Heterogeneous Catalyst for the Synthesis of 5-Arylidine Barbituric Acid Derivatives,” Bulletin of the Korean Chemical Society 31, no. 2 (2010): 339–43.
  • J. K. Rajput, and J. Kaur, “CoFe2O4 Nanoparticles: An Efficient Heterogeneous Magnetically Separable Catalyst for “Click” Synthesis of Arylidene Barbituric Acid Derivatives at Room Temperature,” Chinese Journal of Catalysis 34, no. 9 (2013): 1697–704.
  • N. R. Dighore, P. L. Anandgaonker, S. T. Gaikwad, and A. S. Rajbhoj, “Solvent Free Green Synthesis of 5-Arylidine Barbituric Acid Derivatives Catalyzed by Copper Oxide Nanoparticles,” Research Journal of Chemical Sciences 4 (2014): 93–8.

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.