174
Views
7
CrossRef citations to date
0
Altmetric
Research Articles

An Environment-Friendly Method for Green Synthesis of Pyranopyrazole Derivatives Catalyzed by CoCuFe2O4 Magnetic Nanocrystals under Solvent-Free Conditions

&
Pages 204-217 | Received 04 Dec 2019, Accepted 31 Jan 2020, Published online: 12 Feb 2020

References

  • N. P. Prajapati, R. H. Vekariya, and H. D. Patel, “Ceric Ammonium Nitrate (CAN)–Catalyzed Multicomponent Reactions: An Efficient Catalyst for Green Organic Synthesis,”Synthetic Communications 45, no. 21 (2015): 2399–425.
  • R. H. Vekariya, and H. D. Patel, “Sulfonic Acid Functionalized Silica (SiO2-Pr-SO3H) as a Solid and a Heterogeneous Catalyst in Green Organic Synthesis: Recent Advances,”Synthetic Communications 45, no. 9 (2015): 1031–54.
  • K. Tanaka, Solvent-Free Organic Synthesis, (Weinheim: Wiley-VCH, GmbH and KGaA, 2004).
  • M. A. Zolfigol, A. Khazaei, A. R. Moosavi-Zare, and A. Zare, “Ionic Liquid 3-Methyl-1-Sulfonic Acid Imidazolium Chloride as a Novel and Highly Efficient Catalyst for the Very Rapid Synthesis of Bis (Indolyl)Methanes under Solvent-Free Conditions,”Organic Preparations and Procedures International 42, no. 1 (2010): 95–102.
  • A. Khazaei, M. A. Zolfigol, A. R. Moosavi-Zare, A. Zare, M. Khojasteh, Z. Asgari, V. Khakyzadeh, and A. Khalafi- Nezhad, “Organocatalyst Trityl Chloride Efficiently Promoted the Solvent-Free Synthesis of 12-Aryl-8,9,10,12-Tetrahydrobenzo[a]-Xanthen-11-Ones by in Situ Formation of Carbocationic System in Neutral Media,” Catalysis Communications 20, (2012): 54–7.
  • S. Ambethkar, V. Padmini, and N. Bhuvanesh, “A Green and Efficient Protocol for the Synthesis of Dihydropyrano[2,3-c] Pyrazole Derivatives via a One-Pot, Four Component Reaction by Grinding Method,”Journal of Advanced Research 6, no. 6 (2015): 975–85.
  • M. Beerappa, and K. Shivashankar, “Multicomponent Reaction of Benzyl Halides: Synthesis of [1,2,4] Triazolo/Benzimidazolo Quinazolinones,”Synthetic Communications 46, no. 5 (2016): 421–32.
  • M. Beerappa, and K. Shivashankar, “One Pot Synthesis of Pyran-Based Heterocycles from Benzyl Halides as Key Reagents,”RSC Advances 5, no. 38 (2015): 30364–71.
  • N. Jagadishbabu, and K. Shivashankar, “One Pot Synthesis of Acridine Analogues from 1,2-Diols as Key Reagents,” Rsc Advances 5, no. 115 (2015): 95240–6.
  • D. Shamala, K. Shivashankar, and M. M. Chandra, “Synthesis of N1 and N2 Coumarin Substituted 1,2,3-Triazole Isomers via Click Chemistry Approach,”Synthetic Communications 46, no. 5 (2016): 433–41.
  • (a) Y. Gu, “Multicomponent Reactions in Unconventional Solvents: State of the Art,” Green Chemistry 14, no. 8 (2012): 2091–2128. (b) N. M. Hilmy-Elnagdi, N.S. Al-Hokbany, “Organocatalysis in Synthesis: L-Proline as an Enantioselective Catalyst in the Synthesis of Pyrans and Thiopyrans,” Molecules 17, no. 4 (2012): 4300–4312.
  • A. Hasaninejad, A. Zare, M. Shekouhy, and J. Ameri Rad, “Catalyst-Free One-Pot Four Component Synthesis of Polysubstituted Imidazoles in Neutral Ionic Liquid 1-Butyl-3-Methylimidazolium Bromide,”Journal of Combinatorial Chemistry 12, no. 6 (2010): 844–9.
  • D. S. Fischer, G. M. Allan, C. Bubert, N. Vicker, A. Smith, H. J. Tutill, A. Purohit, L. Wood, G. Packham, M. F. Maho, et al. “E-Ring Modified Steroids as Novel Potent Inhibitors of 17β-Hydroxysteroid Dehydrogenase Type 1,”Journal of Medicinal Chemistry 48, no. 18 (2005): 5749–70.
  • V. K. Ahluwalia, A. Dahiya, and V. K. Garg, “Reaction of 5‐Amino‐4‐Formyl‐3‐Methyl (or Phenyl)‐1‐Phenyl‐1H‐Pyrazoles with Active Methylene Compounds: Synthesis of Fused Heterocyclic Rings,” Cheminform 36, no. 1 (1997): 88–90.
  • M. E. A. Zaki, H. A. Soliman, O. A. Hiekal, and A. E. Z. Rashad, “Pyrazolopyranopyrimidines as a Class of anti-Inflammatory Agents,”Zeitschrift für Naturforschung C 61, no. 1–2 (2006): 1–5.
  • T. N. Bansode, R. M. Ansari, and Y. K. Gawale, “Synthesis and Biological Activity of Some New Pyrazole Derivatives,”Journal of Pharmacy Research 4, no. 4 (2011): 1141–2.
  • 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 97, no. 13 (2000): 7124–9.
  • Z. H. Ismail, G. M. Aly, M. S. El-Degwi, H. I. Heiba, and M. M. Ghorab, “Synthesis and Insecticidal Activity of Some New Pyranopyrazoles, Pyrazolopyranopyrimidines, and Pyrazolopyranopyridines,” Egyptian Journal of Biotechnology 13, (2003): 73–82.
  • M. Beerappa, and K. Shivashankar, “Four Component Synthesis of Highly Functionalized Pyrano [2, 3-c] Pyrazoles from Benzyl Halides,”Synthetic Communications 48, no. 2 (2018): 146–54.
  • M. M. Kamel, “Convenient Synthesis, Characterization, Cytotoxicity and Toxicity of Pyrazole Derivatives,”Acta Chimica Slovenica 62, no. 1 (2015): 136–51.
  • B. Myrboh, H. Mecadon, M. R. Rohman, M. Rajbangshi, I. Kharkongor, B. M. Laloo, I. Kharbangar, and B. Kshiar, “Synthetic Developments in Functionalized Pyrano[2,3-c] Pyrazoles. A Review,”Organic Preparations and Procedures International 45, no. 4 (2013): 253–303.
  • A. Shaabani, A. Sarvary, A. H. Rezayan, and S. Keshipour, “Synthesis of Fully Substituted Pyrano[2,3-c] Pyrazole Derivatives via a Multicomponent Reaction of Isocyanides,”Tetrahedron 65, no. 17 (2009): 3492–5.
  • D. Enders, A. Grossmann, B. Gieraths, M. Düzdemir, and C. Merkens, “Organocatalytic One-Pot Asymmetric Synthesis of 4H, 5H-Pyrano[2,3-c] Pyrazoles,” Organic Letters 14, no. 16 (2012): 4254–7.
  • A. M. Zonouz, I. Eskandari, and H. R. Khavasi, “A Green and Convenient Approach for the Synthesis of Methyl 6-Amino-5-Cyano-4-Aryl-2,4-Dihydropyrano[2,3-c]Pyrazole-3-Carboxylates via a One-Pot, Multi-Component Reaction in Water,”Tetrahedron Letters 53, no. 41 (2012): 5519–22.
  • D. M. Pore, P. B. Patil, D. S. Gaikwad, P. G. Hegade, J. D. Patil, and K. A. Undale, “Green Access to Novel Spiro Pyranopyrazole Derivatives,”Tetrahedron Letters 54, no. 44 (2013): 5876–8.
  • S. Kanchithalaivan, S. Sivakumar, R. R. Kumar, P. Elumalai, Q. N. Ahmed, and A. K. Padala, “Four-Component Domino Strategy for the Combinatorial Synthesis of Novel 1,4-Dihydropyrano[2,3-c] Pyrazol-6-Amines,” Acs Combinatorial Science 15, no. 12 (2013): 631–8.
  • Y. Zou, Y. Hu, H. Liu, and D. Shi, “Rapid and Efficient Ultrasound-Assisted Method for the Combinatorial Synthesis of Spiro[Indoline-3,4′-Pyrano[2,3-c] Pyrazole] Derivatives,” Acs Combinatorial Science 14, no. 1 (2012): 38–43.
  • G. Deng, F. Wang, S. Lu, and B. Cheng, “Synthesis of Pyrano[3,2-c] Pyrazol-7(1H)-One Derivatives by Tandem Cyclization of 2-Diazo-3,5-Dioxo-6-Ynoates (Ynones),”Organic Letters 17, no. 19 (2015): 4651–3.
  • M. Zolfigol, M. Tavasoli, A. Moosavi-Zare, P. Moosavi, H. Kruger, Morteza Shiri, and Vahid Khakyzadeh, “Synthesis of Pyranopyrazoles Using Isonicotinic Acid as a Dual and Biological Organocatalyst,”RSC Advances 3, no. 48 (2013): 25681–5.
  • S. Gogoi, and C. G. Zhao, “Organocatalyzed Enantioselective Synthesis of 6-Amino-5-Cyanodihydropyrano[2,3-c] Pyrazoles,”Tetrahedron Letters 50, no. 19 (2009): 2252–5.
  • A. Keyume, Z. Esmayil, L. Wang, and F. Jun, “Convenient DABCO-Catalyzed One-Pot Synthesis of Multi-Substituted Pyrano[2,3-c] Pyrazole Dicarboxylates,”Tetrahedron 70, no. 26 (2014): 3976–80.
  • Y. A. Tayade, S. A. Padvi, Y. B. Wagh, and D. S. Dalal, “β-Cyclodextrin 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.
  • 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.
  • 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.
  • 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.
  • S. Sun, H. Zeng, D. B. Robinson, S. Raoux, P. M. Rice, S. X. Wang, and G. Li, “Monodisperse MFe2O4 (M = Fe, Co, Mn) Nanoparticles,”Journal of the American Chemical Society 126, no. 1 (2004): 273–9.
  • C. D. Lokhande, D. P. Dubal, and O. S. Joo, “Metal Oxide Thin Filmbased Supercapacitors,”Current Applied Physics 11, no. 3 (2011): 255–70.
  • J. L. Gunjakar, A. M. More, K. V. Gurav, and C. D. Lokhande, “Chemical Synthesis of Spinel Nickel Ferrite (NiFe2O4) Nano-Sheets,”Applied Surface Science 254, no. 18 (2008): 5844–8.
  • B. Bhujun, M. T. T. Tan, and A. S. Shanmugam, “Study of Mixed Ternary Transition Metal Ferrites as Potential Electrodes for Supercapacitor Applications,” Results in Physics 7, (2017): 345–53.
  • H. Naeimi, and Z. S. Nazifi, “A Highly Efficient nano-Fe3O4 Encapsulated-Silica Particles Bearing Sulfonic Acid Groups as a Solid Acid Catalyst for Synthesis of 1,8-Dioxo-Octahydroxanthene Derivatives,”Journal of Nanoparticle Research 15, no. 11 (2013): 2026.
  • H. Naeimi, Z. Rashid, A. H. Zarnani, and R. Ghahremanzadeh, ” “Nanocrystalline Magnesium Oxide: An Efficient Promoter and Heterogeneous Nano Catalyst for the One-Pot Synthesis of Pyrazolotriazoles in Green Medium,”Journal of Nanoparticle Research 16, no. 5 (2014): 2416.
  • M. Farahnak Zarabi, and H. Naeimi, “Ultrasound Promoted Synthesis of Benzo[a]Pyra[2,3-c] Phenazines Using Multisulfonic Acid Hyperbranched Polyglycerol Functionalized Graphene Oxide as a Novel and Reusable Catalyst,” Polycyclic Aromatic Compounds (2019): 1–20. doi:https://doi.org/10.1080/10406638.2019.1672202
  • A. S. Albuquerque, J. D. Ardisson, W. A. A. Macedo, and M. C. M. Alves, “Nanosized Powders of NiZn Ferrite: Synthesis, Structure, and Magnetism,”Journal of Applied Physics 87, no. 9 (2000): 4352–7.
  • H. V. Chavan, S. B. Babar, R. U. Hoval, and B. P. Bandgar, “Rapid One-Pot, Four Component Synthesis of Pyranopyrazoles Using Heteropolyacid under Solvent-Free Condition,”Bulletin of the Korean Chemical Society 32, no. 11 (2011): 3963–6.
  • H. Mecadon, M. R. Rohman, M. Rajbangshi, and B. Myrboh, “γ-Alumina as a Recyclable Catalyst for the Four-Component Synthesis of 6-Amino-4-Alkyl/Aryl-3-Methyl-2,4-Dihydropyrano[2,3-c]Pyrazole-5-Carbonitriles in Aqueous Medium,”Tetrahedron Letters 52, no. 19 (2011): 2523–5.
  • F. Tamaddon, and M. A. 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.
  • T. Zhang, J. Zhou, Y. Chen, and Y. Li, “Ce (III) Immobilized on Aminated Poly (Vinyl Chloride): High-Performance Synergistic Bifunctional Acid–Base Catalyst for One-Pot Synthesis of 1,4-Dihydropyrano[2,3-c] Pyrazoles,”Research on Chemical Intermediates 44, no. 9 (2018): 5329–44.
  • R. Ghorbani-Vaghei, and V. Izadkhah, “Preparation and Characterization of Hexamethylenetetramine‐Functionalized Magneticnanoparticles and Their Application as Novel Catalyst for Thesynthesis of Pyranopyrazole Derivatives,”Applied Organometallic Chemistry 32, no. 2 (2018): e4025.
  • A. B. Atar, J. T. Kim, K. T. Lim, and Y. T. Jeong, “Synthesis of 6-Amino-2,4-Dihydropyrano[2,3-c] Pyrazol-5-Carbonitriles Catalyzed by Silica-Supported Tetramethylguanidine under Solvent-Free Conditions,”Synthetic Communications 44, no. 18 (2014): 2679–91.
  • H. M. Al-Matar, K. D. Khalil, A. Y. Adam, and M. H. Elnagdi, “Green One Pot Solvent-Free Synthesis of Pyrano[2,3-c]-Pyrazoles and Pyrazolo[1,5-a] Pyrimidines,”Molecules 15, no. 9 (2010): 6619–29.
  • A. R. Moosavi-Zare, M. A. Zolfigol, and A. Mousavi-Tashar, “Synthesis of Pyranopyrazole Derivatives by in Situ Generation of Trityl Carbocation under Mild and Neutral Media,”Research on Chemical Intermediates 42, no. 10 (2016): 7305–12.
  • B. P. Tripathi, A. Mishra, P. Rai, Y. K. Pandey, M. Srivastava, S. Yadav, J. Singhb, and J. Singh, “A Green and Clean Pathway: One Pot, Multicomponent, Visible Light Assisted Synthesis of Pyrano[2,3-c]Pyrazoles under Catalyst-Free and Solvent-Free Conditions,”New Journal of Chemistry 41, no. 19 (2017): 11148–54.
  • M. R. Bhosle, L. D. Khillare, S. T. Dhumal, and R. A. Mane, “A Facile Synthesis of 6-Amino-2H, 4H-Pyrano[2,3-c] Pyrazole-5-Carbonitriles in Deep Eutectic Solvent,”Chinese Chemical Letters 27, no. 3 (2016): 370–4.

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.