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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 48, 2018 - Issue 15
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Original Articles

NaF-catalyzed efficient one-pot synthesis of dihydropyrano[2,3-c]pyrazoles under ultrasonic irradiation via MCR approach

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Pages 1994-2001 | Received 19 Mar 2018, Published online: 28 Jun 2018

References

  • Anastas, P. T.; Williamson, T. C. Green Chemistry: Frontiers in Chemical Synthesis and Processes, Edn Oxford University Press: Oxford, 1998. pp. 364+xvii
  • Anastas, P.; Williamson, T. C. Green Chemistry: Theory and Practice. Oxford University Press: Oxford. 1998. pp. 135+xi
  • Anastas, P. T.; Kirchhoff, M. M. Origins, Current Status, and Future Challenges of Green Chemistry. Acc. Chem. Res. 2002, 35, 686.
  • Bhosle, M. R.; Khillare, L. D.; Dhumal, S. T.; Man, R. A. A Facile Synthesis of 6-Amino-2H, 4H-Pyrano[2,3-с]Pyrazole-5-Carbonitriles in Deep Eutectic Solvent. Chin. Chem. Lett 2016, 27, 370–374.
  • Zou, Y.; Wu, H.; Hu, Y.; Liu, H.; Zhao, X.; Ji, H.; Shi, D. A Novel and environment-friendly method for preparing dihydropyrano[2,3-c]pyrazoles in water under ultrasound irradiation. Ultrason. Sonochem. 2011, 18, 708–712.
  • Zonouz, A. M.; Eskandari, I.; Khavasi, H. R. 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. Lett. 2012, 53, 5519–5522.
  • Nishtala, V. B.; Nanubolu, J. B.; Basavoju, S. Ultrasound-Assisted Rapid and Efficient One-Pot Synthesis of Furanyl Spirooxindolo and Spiroquinoxalinopyrrolizidines by 1,3-Dipolar Cycloaddition: A Green Protocol. Res. Chem. Intermed. 2017, 43, 1365–1381.
  • Mecadon, H.; Rohman, Md, R.; Rajbangshi, M.; Myrboh, B. 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 Lett. 2011, 52, 2523–2525.
  • Mecadon, H.; Rohman, Md, R.; Harbangar, I.; Laloo, B. M.; Kharkongor, I.; Rajbangshi, M.; Myrboh, B. 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 Lett 2011, 52, 3228–3231.
  • Brahmachari, G.; Banerjee, B. Facile and One-Pot Access to Diverse and Densely Functionalized 2-Amino-3-Cyano-4 H -Pyrans and Pyran-Annulated Heterocyclic Scaffolds via an Eco-Friendly Multicomponent Reaction at Room Temperature Using Urea as a Novel Organo-Catalyst. ACS Sustainable. Chem. Eng. 2014, 2, 411–422.
  • Zou, Y.; Hu, Y.; Liu, H.; Shi, D. Rapid and Efficient Ultrasound-Assisted Method for the Combinatorial Synthesis of Spiro[indoline-3,4′-pyrano[2,3-c]pyrazole] Derivatives. ACS Comb. Sci 2012, 14, 38–43.
  • Bihani, M.; Bora, P. P.; Bez, G.; Askari, H. Amberlyst A21 Catalyzed Chromatography-Free Method for Multicomponent Synthesis of Dihydropyrano[2,3-c]Pyrazoles in Ethanol. ACS Sustainable. Chem. Eng. 2013, 1, 440–447.
  • (a) Smith, W. P.; Sollis, L. S.; Howes, D. P.; Cherry, P. C.; Starkey, I. D.; Cobley, K. N.; Weston, H.; Scicinski, J.; Merritt, A.; Whittington, A.; et al. Dihydropyrancarboxamides Related to Zanamivir: A New Series of Inhibitors of Influenza Virus Sialidases. 1. Discovery, Synthesis, Biological Activity, and Structure-Activity Relationships of 4-Guanidino- and 4-Amino-4H-Pyran-6-Carboxamides. J. Med. Chem. 1998, 41, 787–797. (b) Mazaahir, K.; Shilpi, S.; Khalilur, R. K.; Sharanjit, S. T. Aqua mediated synthesis of substituted 2-amino-4H-chromenes and in vitro study as antibacterial agents. Bioorg. Med. Chem. Lett 2005, 15, 4295–4298.
  • Wang, J. L.; Liu, D.; Zhang, Z. J.; Shan, S.; Han, X.; Srinivasula, S. M.; Croce, C. M.; Alnemri, E. S.; Huang, Z. Structure-Based Discovery of an Organic Compound That Binds Bcl-2 Protein and Induces Apoptosis of Tumor Cells. Proc. Natl. Acad. Sci. USA. 2000, 97, 7124–7129.
  • (a) Zaki, M. E. A.; Soliman, H. A.; Hiekal, O. A.; Rashad, A. E. Pyrazolopyranopyrimidines as a Class of anti-Inflammatory Agents. Z. Naturforsch., C, J. Biosci NaturforschCJBiosci. 2006, 61, 1–5. (b) Sheng, C. K.; Li, J. H.; Hideo, N. Studies on Heterocyclic Compounds. 6. Synthesis and Analgesic and Antiinflammatory Activities of 3,4-Dimethylpyrano[2,3-c]Pyrazol-6-One Derivatives. J. Med. Chem. 1984, 27, 539–544.
  • Foloppe, N.; Fisher, L. M.; Howes, R.; Potter, A.; Robertson, A. G. S.; Surgenor, A. E. Identification of Chemically Diverse Chk1 Inhibitors by Receptor-Based Virtual Screening. Bioorg. Med. Chem. 2006, 14, 4792–4802.
  • Fatahpour, M.; Sadeh, F. N.; Hazeri, N.; Maghsoodlou, M. T.; Hadavi, Md. S.; Mahnaei, S. Jour. of Saudi Chem. Soc. 2017. https://doi.org/10.1016/j.jscs.2017.05.009
  • Tamaddon, F.; Alizadeh, M. A Four-Component Synthesis of Dihydropyrano[2,3-c]Pyrazoles in a New Water-Based Worm-like Micellar Medium. Tetrahedron Lett. 2014, 55, 3588–3591.
  • Ku c u Kguzel, S. G.; Senkardes, S. Recent Advances in Bioactive Pyrazoles. Eur. J. Med. Chem 2015, 97, 786–815.
  • Kasiotis, K. M.; Tzanetou, E. N.; Haroutounian, S. A. Pyrazoles as Potential anti-Angiogenesis Agents: A Contemporary Overview. Front. Chem. 2014, 2, 1–7.
  • Kiyani, H.; Samimi, H. A.; Ghorbani, F.; Esmaieli, S. One-Pot, Four-Component Synthesis of Pyrano[2,3-c]Pyrazoles Catalyzed by Sodium Benzoate in Aqueous Medium. 105267/Jccl. 2013, 2, 197–206.
  • Babaie, M.; Sheibani, H. Nanosized Magnesium Oxide as a Highly Effective Heterogeneous Base Catalyst for the Rapid Synthesis of Pyranopyrazoles via a Tandem Four-Component Reaction. Arabian J. Chem. 2011, 4, 159–162.
  • Vekariya, R. H.; Patel, K. D.; Patel, H. D. Fruit Juice of Citrus Limon as a Biodegradable and Reusable Catalyst for Facile, Eco-Friendly and Green Synthesis of 3,4-Disubstituted Isoxazol-5(4H)-Ones and Dihydropyrano[2,3-c]-Pyrazole Derivatives. Res. Chem. Intermed. 2016, 42, 7559–7579.
  • Ghomi, J. S.; Koopaei, B. K.; Alavi, H. Pseudo Five-Component Process for the Synthesis of 4,4′-(Arylmethylene)Bis(3-Methyl-1H-Pyrazol-5-Ol) Derivatives Using ZnAl2O4 Nanoparticles in Aqueous Media. S. RSC Adv. 2014, 4, 46106–46113.
  • Paul, S.; Pradhan, K.; Ghosh, S.; De, S. K.; Das, A. R. Uncapped SnO2 Quantum Dot Catalyzed Cascade Assembling of Four Components: A Rapid and Green Approach to the Pyrano[2,3-c]Pyrazole and Spiro-2-Oxindole Derivatives. Tetrahedron. 2014, 70, 6088–6099.
  • Maleki, B.; Eshghi, H.; Barghamadi, M.; Nasiri, N.; Khojastehnezhad, A.; Sedigh Ashrafi, S.; Pourshiani, O. 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. Res. Chem. Intermed. 2016, 42, 3071–3093.
  • Ablajan, K.; Liju, W.; Kelimu, Y.; Jun, F. Cerium Ammonium Nitrate (CAN)-Catalyzed Four-Component One-Pot Synthesis of Multi-Substituted Pyrano[2,3-c] Pyrazoles under Ultrasound Irradiation. Mol. Divers. 2013, 17, 693–700.
  • Iskalieva, A.; Yimmou, B. M.; Gogate, P. R.; Horvath, M.; Horvath, P. G.; Csoka, L. Cavitation Assisted Delignification of Wheat Straw: A Review. Ultrason. Sonochem. 2012, 19, 984.

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