New eco-friendly procedure for the synthesis of 4-arylmethylene-isoxazol-5(4H)-ones catalyzed by pyridinium p-toluenesulfonate (PPTS) in aqueous medium

References

• Ishioka, T.; Tanatani, A.; Nagasawa, K.; Hashimoto, Y. Anti-Androgens with Full Antagonistic Activity toward Human Prostate Tumor LNCaP Cells with Mutated Androgen Receptor. Bioorg. Med. Chem. Lett. 2003, 13, 2655–2658. DOI:10.1016/S0960-894X(03)00575-4.
   PubMed Web of Science ®Google Scholar
• Mazimba, O.; Wale, K.; Loeto, D.; Kwape, T. Antioxidant and Antimicrobial Studies on Fused-Ring Pyrazolones and Isoxazolones. Bioorg. Med. Chem. 2014, 22, 6564–6569. DOI:10.1016/j.bmc.2014.10.015.
   PubMed Web of Science ®Google Scholar
• Laughlin, S. K.; Clark, M. P.; Djung, J. F.; Golebiowski, A.; Brugel, T. A.; Sabat, M.; Bookland, R. G.; Laufersweiler, M. J.; VanRens, J. C.; Townes, J. A.; et al. The Development of New Isoxazolone Based Inhibitors of Tumor Necrosis Factor-Alpha (TNF-Alpha) Production. Bioorg. Med. Chem. Lett. 2005, 15, 2399–2403. DOI:10.1016/j.bmcl.2005.02.066.
   PubMed Web of Science ®Google Scholar
• Kafle, B.; Cho, H. Isoxazolone Derivatives as Potent Inhibitors of PTP1B. Bull. Korean Chem. Soc. 2012, 33, 275–278. DOI:10.5012/bkcs.2012.33.1.275.
   Web of Science ®Google Scholar
• Lowe, D. B.; Magnuson, S.; Qi, N.; Campbell, A.-M.; Cook, J.; Hong, Z.; Wang, M.; Rodriguez, M.; Achebe, F.; Kluender, H.; et al. In Vitro SAR of (5-(2H)-Isoxazolonyl) Ureas, Potent Inhibitors of Hormone-Sensitive Lipase. Bioorg. Med. Chem. Lett. 2004, 14, 3155–3159. DOI:10.1016/j.bmcl.2004.04.015.
   PubMed Web of Science ®Google Scholar
• European Patent. EP042064A2. 3-Isoxazolones derivatives, their preparation and their therapeutic uses, 1993.
   Google Scholar
• US Patent. US 4044018 A. Isoxazolone derivatives, their preparation and their use as plant growth regulators. 1977.
   Google Scholar
• Miyake, T.; Yagasaki, Y.; Kagabu, S. Potential New Fungicides: N-Acyl-5-Methyl-3(2H)-Isoxazolone Derivatives. J. Pestic. Sci. 2012, 37, 89–94. DOI:10.1584/jpestics.D11-004.
   Web of Science ®Google Scholar
• Zhang, X.-H.; Zhan, Y.-H.; Chen, D.; Wang, F.; Wang, L.-Y. Merocyanine Dyes Containing an Isoxazolone Nucleus: Synthesis, X-Ray Crystal Structures, Spectroscopic Properties and DFT Studies. Dyes Pigments 2012, 93, 1408–1415. DOI:10.1016/j.dyepig.2011.10.003.
   Web of Science ®Google Scholar
• Tu, S.; Zhang, J.; Jia, R.; Jiang, B.; Zhang, Y.; Jiang, H. An Efficient Route for the Synthesis of a New Class of Pyrido[2,3-d]Pyrimidine Derivatives. Org. Biomol. Chem. 2007, 5, 1450–1453. DOI:10.1039/b617201f.
   PubMed Web of Science ®Google Scholar
• Beccalli, E. M.; La Rosa, C.; Marchesini, A. Oxidation of 4-Aryl-Substituted Isoxazolin-5-Ones. A New Synthesis of 2,5-Diaryl-1,3-Oxazin-6-Ones. J. Org. Chem. 1984, 49, 4287–4290. DOI:10.1021/jo00196a034.
   Web of Science ®Google Scholar
• Beccalli, E. M.; Marchesini, A.; Pilati, T. Synthesis 1991, 1991, 127–131. DOI:10.1055/s-1991-26396.
   Google Scholar
• Abbiati, G.; Beccalli, E. M.; Broggini, G.; Zoni, C. A Valuable Heterocyclic Ring Transformation: From Isoxazolin-5(2H)-Ones to Quinolines. Tetrahedron 2003, 59, 9887–9893. DOI:10.1016/j.tet.2003.10.053.
   Web of Science ®Google Scholar
• Batra, S.; Bhaduri, A. P. J. Ind. Sci. 1994, 74, 213–226.
   Web of Science ®Google Scholar
• Kausar, R.; Akhtar, N.; Gomha, S. M. Int. J. Pharm. Pharm. Sci. 2016, 9, 236–239. DOI:10.22159/ijpps.2017v9i1.15123.
   Google Scholar
• Villemin, D.; Martin, B.; Garrigues, B. Potassium Fluoride on Alumina: Dry Condensation of 3-Phenylisoxazol-5-One with Aldehydes under Microwave Irradiation. Synth. Commun. 1993, 23, 2251–2257. DOI:10.1080/00397919308013781.
   Web of Science ®Google Scholar
• Zhang, Y.-Q; Ma, J.–J.; Wang, C.; Li, J.–C.; Zhang, D.–N.; Zang, X.–H., Li, J. Chin. J. Org. Chem. 2008, 28, 141–144.
   Web of Science ®Google Scholar
• Vekariya, R. H.; Prajapati, N. P., Patel, K. D., Mayur, K., Vekariya, M. K., Dhaval, B., Patel, D. B., Hitesh, D., Patel, H. D. W. J. P. P. S., 2017, 6, 2003–2036..
   Google Scholar
• Liu, Q.; Wu, R. -T. Facile Synthesis of 3-Methyl-4-Arylmethylene-Isoxazol-5(4H)-Ones Catalysed by Sodium Silicate in an Aqueous Medium. J. Chem. Res. (S) 2011, 35, 598–599. DOI:10.3184/174751911X13176501108975.
   Google Scholar
• Kiyani, H.; Ghorbani, F. Boric Acid-Catalyzed Multi-Component Reaction for Efficient Synthesis of 4H-Isoxazol-5-Ones in Aqueous Medium. Res. Chem. Intermed. 2015, 41, 2653–2664. DOI:10.1007/s11164-013-1411-x.
   Web of Science ®Google Scholar
• Setamdideh, D. J. Mex. Chem. Soc. 2015, 59, 191–197.
   Google Scholar
• Liu, Q.; Zhang, Y. N. One-Pot Synthesis of 3-Methyl-4-Arylmethylene-Isoxazol-5(4H)-Ones Catalyzed by Sodium Benzoate in Aqueous Media: A Green Chemistry Strategy. Bull. Korean Chem. Soc. 2011, 32, 3559–3560. DOI:10.5012/bkcs.2011.32.10.3559.
   Web of Science ®Google Scholar
• Amine Khodja, I.; Boulcina, R.; Boumoud, T.; Boumoud, B.; Debache, A. Der. Pharm. Chem. 2016, 8, 97–101.
   Web of Science ®Google Scholar
• Pawar, G. T.; Gadecar, S. P.; Arbad, B. R.; Lande, M. K. Bull. Chem. Reac. Engi. Cat. 2017, 12, 32–40. DOI:10.9767/bcrec.12.1.655.32-40.
   Web of Science ®Google Scholar
• Ghosh, S.; Saikh, F.; Das, J.; Pramanik, A. K. Hantzsch 1,4-Dihydropyridine Synthesis in Aqueous Ethanol by Visible Light. Tetrahedron Lett. 2013, 54, 58–4682. DOI:10.1016/j.tetlet.2012.10.079.
   Web of Science ®Google Scholar
• Safari, J.; Ahmadzadeh, M.; Zarnegar, Z. Org. Chem. Res. 2016, 2, 134–139.
   Google Scholar
• Fozooni, S.; Hosseinzadeh, N. G.; Hamidian, H., Akhgar, M. R. J. Braz. Chem. Soc. 2013, 24, 1649–1655.
   Web of Science ®Google Scholar
• Khandebharad, A. U.; Sarda, S. R.; Gill, C. H.; Agrawal, B. R. Res. J. Chem. Sci. 2015, 5, 27–32.
   Google Scholar
• Kiyani, H.; Ghorbani, F. Open J. Org. Chem. 2013, 1, 5–9.
   Google Scholar
• Kiyani, H. Org. Chem: Indian J., 2013, 9, 97–101.
   Google Scholar
• Rikani, A. B.; Setamdideh, D. One-Pot and Three-Component Synthesis of Isoxazol-5(4H)-One Derivatives in the Presence of Citric Acid. Orient. J. Chem. 2016, 32, 1433–1437. DOI:10.13005/ojc/320317.
   Web of Science ®Google Scholar
• Kiyani, H., Ghorbani, F. Heterocycl. Lett. 2013, 3, 359–369.
   Google Scholar
• Chavan, A. P.; Pinjari, A. B.; Mhaske, P. C. An Efficient Synthesis of 4-Arylmethylidene-3-Substituted-Isoxazol-5(4 H )-Ones in Aqueous Medium. J. Heterocyclic Chem. 2015, 52, 1911–1915. DOI:10.1002/jhet.2293.
   Web of Science ®Google Scholar
• Ganeshpure, P. A.; Das, J. Application of High-Melting Pyridinium Salts as Ionic Liquid Catalysts and Media for Fischer Esterification. React. Kinet. Catal. Lett. 2007, 92, 69–74. DOI:10.1007/s11144-007-5077-5.
   Google Scholar
• Boese, D.; Niesobski, P.; Luebcke, M.; Pietruszka, J. 2014, 45, no–733.
   Google Scholar
• Thatipally, S.; Acharyulu, P. V. R.; Dubey, P. K. Asian J. Chem. 2011, 23, 451–454.
   Google Scholar
• Boureghda, C.; Amine Khodja, I.; Carboni, B.; Boulcina, R.; Kermiche, O.; Debache, A. A Facile One-Pot and Green Multi-Component Synthesis of 2-Amino-4Hpyrans Promoted by Pyridinium p-Toluenesulfonate in Aqueous Medium. LOC 2016, 13, 482–490., DOI:10.2174/1570178613666160822164749.
   Web of Science ®Google Scholar
• Mahdjoub, S.; Derabli, C.; Boulcina, R.; Kirsch, G.; Debache, A. Design and Synthesis of Novel 2-Hydroxy-1,4-Benzoxazine Derivatives through Three-Component Petasis Reaction Catalysed by Pyridinium Toluene-Sulphonate. J. Chem. Res. (S) 2016, 40, 449–452., DOI:10.3184/174751916X14656634976813.
   Google Scholar
• Amine Khodja, I.; Boulcina, R.; Debache, A. Lett. Org. Chem. 2015, 12, 77–84. DOI:10.2174/1570178612666141226193727.
   Web of Science ®Google Scholar