Sonochemical synthesis of methyl-4-(hetero)arylmethylene isoxazole-5(4H)-ones using Sn^II-montmorillonite

References

• (a) Brahmachari, G.; Banerjee, B. Facile and One-pot Access to Diverse and Densely Functionalized 2-amino-3-cyano-4H-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; (b) Solhy, A.; Elmakssoudi, A.; Tahir, R.; ed Karkouri, M.; Larzek, M.; Bousmina, M.; Zahouily, M. Clean Chemical Synthesis of 2-amino-chromenes in Water Catalyzed by Nanostructured Diphosphate Na2CaP2O7. Green Chem. 2010,12, 2261–2267. doi: 10.1021/sc400312n
   Web of Science ®Google Scholar
• (a) Ramazani, A.; Asiabi, P.A.; Aghahosseini, H.; Gouranlou, F. Review on the Synthesis and Functionalization of SiO2 Nanoparticles as Solid Supported Catalysts. Curr. Org. Chem. 2017, 21, 908–922; (b) Khoobi, M.; Ma’mani, L.; Rezazadeh, F.; Zareie, Z.; Foroumadi, A.; Ramazani, A.; Shafiee, A. One-pot Synthesis of 4H-benzo[b]pyrans and Dihydropyrano[c]chromenes Using Inorganic – Organic Hybrid Magnetic Nanocatalyst in Water. J. Mol. Catal. A Chem. 2012,359, 74–80; (c) Tabatabaei Rezaei, S.J.; Shamseddin, A.; Ramazani, A.; Mashhadi Malekzadeh, A.; Azimzadeh Asiabi, P. Palladium Nanoparticles Immobilized on Amphiphilic and Hyperbranched Polymer-functionalized Magnetic Nanoparticles: An Efficient Semi-heterogeneous Catalyst for Heck Reaction. Appl. Organomet. Chem. 2017, in press. DOI:10.1002/aoc.3707; (d) Fardood, S.T.; Ramazani, A.; Golfar, Z.; Joo, S.W. Green Synthesis of Ni-Cu-Zn Ferrite Nanoparticles Using Tragacanth Gum and Their Use as An Efficient Catalyst for the Synthesis of Polyhydroquinoline Derivatives. Appl. Organomet. Chem. 2017, in press. DOI: 10.1002/aoc.3823; (e) Hasanpour, Z.; Maleki, A.; Hosseini, M.; Gorgannezhad, L.; Nejadshafiee, V.; Ramazani, A.; Haririan, I.; Shafiee, A.; Khoobi, M. Efficient Multicomponent Synthesis of 1,2,3-triazoles Catalyzed by Cu(II) Supported on PEI@Fe3O4 MNPs in a Water/PEG300 System. Turk. J. Chem. 2017,41, 294–307; (f) Taran, J.; Ramazani, A.; Aghahosseini, H.; Gouranlou, F.; Tarasi, R.; Khoobi, M.; Joo, S.W. One-pot Three-component Syntheses of α-aminophosphonates from a Primary Amine, Quinoline-4-Carbaldehyde and a Phosphite in the Presence of MCM-41@PEI as an Efficient Nanocatalyst. Phosphorus, Sulfur, Silicon. Relat. Elem. 2017,192, 776–781. doi: 10.2174/1385272820666161021103415
   Web of Science ®Google Scholar
• Santos, M.M.M.; Faria, N.; Iley, J.; Coles, S.J.; Hursthouse, M.B.; Martins, M.L.; Moreira, R. Reaction of Naphthoquinones with Substituted Nitromethanes. Facile Synthesis and Antifungal Activity of Naphtho[2,3-d]isoxazole-4,9-diones. Bioorg. Med. Chem. Lett. 2010, 20, 193–195. doi: 10.1016/j.bmcl.2009.10.137
   PubMed Web of Science ®Google Scholar
• Kano, H.; Adachi, I.; Kido, R.; Hirose, K. Isoxazoles. XVIII. Synthesis and Pharmacological Properties of 5-aminoalkyl- and 3-aminoalkylisoxazoles and Related Derivatives. J. Med. Chem. 1967, 10, 411–418. doi: 10.1021/jm00315a028
   PubMed Web of Science ®Google Scholar
• Saikh, F.; Das, J.; Ghosh, S. Synthesis of 3-methyl-4-arylmethylene Isoxazole-5(4H)-ones by Visible Light in Aqueous Ethanol. Tetrahedron Lett. 2013, 54, 4679–4682. doi: 10.1016/j.tetlet.2013.06.086
   Web of Science ®Google Scholar
• Padmaja, A.; Rajasekhar, C.; Muranikrishna, A.; Padmavathi, V. Synthesis and Antioxidant Activity of Oxazolyl/Thiazolylsulfonylmethyl Pyrazoles and Isoxazoles. Eur. J. Med. Chem. 2011, 46, 5034–5038. doi: 10.1016/j.ejmech.2011.08.010
   PubMed Web of Science ®Google Scholar
• Srinivas, A.; Nagaraj, A.; Reddy, C.S. Synthesis and In Vitro Study of Methylene-bis-tetrahydro[1,3]thiazolo[4,5-c]isoxazoles as Potential Nematicidal Agents. Eur. J. Med. Chem. 2010, 45, 2353–2358. doi: 10.1016/j.ejmech.2010.02.014
   PubMed Web of Science ®Google Scholar
• Karabasanagouda, T.; Adhikari, A.V.; Girisha, M. Synthesis of Some New Pyrazolines and Isoxazoles Carrying 4-methylthiophenyl Moiety as Potential Analgesic and Anti-inflammatory Agents. Indian J. Chem. 2009, 48B, 430–437.
   Google Scholar
• Kang, Y.Y.; Shin, K.J.; Yo, K.H.; Seo, K.J.; Hong, C.Y.; Lee, C.S.; Park, S.Y.; Kim, D.J.; Park, S.W. Synthesis and Antibacterial Activity of New Carbapenems Containing Isoxazole Moiety. Bioorg. Med. Chem. Lett. 2000, 10, 95–99. doi: 10.1016/S0960-894X(99)00646-0
   PubMed Web of Science ®Google Scholar
• (a) Maddila, S.N.; Maddila, S.; van Zyl, W.E.; Jonnalagadda, S.B. Ag/SiO2 as a Recyclable Catalyst for the Facile Green Synthesis of 3-methyl-4-(phenyl)methylene-isoxazole-5(4H)-ones. Res. Chem. Intermed. 2016, 42, 2553–2566; (b) Kiyani, H.; Darbandi, H.; Mosallanezhad, A.; Ghorbani, F. 2-Hydroxy-5-sulfobenzoic Acid: An Efficient Organocatalyst for the Three-component Synthesis of 1-amidoalkyl-2-naphthols and 3,4-disubstituted isoxazol-5(4H)-ones. Res. Chem. Intermed. 2015,41, 7561–7579; (c) Setamdideh, D. DOWEX(R)50WX4/H2O: A Green System for a One-pot and Three-component Synthesis of Isoxazol-5(4H)-one derivatives. J. Mex. Chem. Soc. 2015,59, 191–197; (d). Patil, M.S.; Mudaliar, C.; Chaturbhuj, G.U. Sulfated Polyborate Catalyzed Expeditious and Efficient Three Component Synthesis of 3-methyl-4-(hetero)arylmethylene Isoxazole-5 (4H)-ones. Tetrahedron Lett. 2017,58, 3256–3261. doi: 10.1007/s11164-015-2167-2
   Web of Science ®Google Scholar
• (a) Liu, Q.; Hou, X. One-pot Three-component Synthesis of 3-methyl-4-arylmethylene-Isoxazol-5(4H)-ones Catalyzed by Sodium Sulfide. Phosphorus Sulfur Silicon Relat. Elem. 2012, 187, 448–453; (b) 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; (c) Kiyani, H.; Kanaani, A.; Ajloo, D.; Ghorbani, F.; Vakili, M. N-bromosuccinimide (NBS)-promoted, Three Component Synthesis of α,β-unsaturated isoxazol-5(4H)- ones, and Spectroscopic Investigation and Computational Study of 3-methyl-4-(thiophen-2-ylmethylene)isoxazol- 5(4H)-one. Res. Chem. Intermed. 2015,41, 7739–7773. doi: 10.1080/10426507.2011.621003
   Web of Science ®Google Scholar
• (a) Mirzazadeh, M.; Mahdavinia, G.H. Fast and Efficient Synthesis of 4-Arylidene-3-phenylisoxazol-5-ones. E- J. Chem. 2012, 9, 425–429; (b) Pawar, G.T.; Gadekar, S.P.; Arbad, B.R.; Lande, M.K. Modification, Characterization, and Catalytic Application of Mesolite for One Pot Synthesis of 3-methyl-4-arylmethylene-isoxazol-5(4H)-ones. Bull. Chem. React. Eng. Catal. 2017,12, 32–40; (c) Kiyani, H.; Ghorbani, F. Expeditious Green Synthesis of 3,4-disubstituted isoxazole-5(4H)-ones Catalyzed by Nano-MgO. Res. Chem. Intermed. 2016,42, 6831–6844; (d) Safari, J.; Ahmadzadeh, M.; Zarnegar, Z. Sonochemical Synthesis of 3-methyl-4-arylmethylene Isoxazole-5(4H)-ones by Amine-modified Montmorillonite Nanoclay. Catal. Comm. 2016,86, 91–95. doi: 10.1155/2012/562138
   Google Scholar
• (a) Zhang, Y.Q.; Ma, J.J.; Wang, C.; Li, J.C.; Zhang, D.N.; Zang, X.H.; Li, J. One-pot Synthesis of 3-methyl-4-arylmethylene-isoxazol-5(4H)-ones. Chin. J. Org. Chem. 2008, 28, 141–144; (b) Chavan, A.P.; Pinjari, A.B.; Mhaske, P.C. An Efficient Synthesis of 4-arylmethylidene-3-substituted-isoxazol-5(4H)-ones in Aqueous Medium. J. Heterocycl. Chem. 2015,52, 1911–1915; (c) Setamdideh, D. One-pot Green Synthesis of Isoxazol-5(4H)-one Derivatives by Dowex1-x8OH in Water. J. Serb. Chem. Soc. 2016,81, 971–978.
   Web of Science ®Google Scholar
• (a) Kiyani, H.; Ghorbani, F. Sodium Saccharin as a Clean and Efficient Catalyst for the Synthesis of 4-arylidene-3methylisoxazol-5(4H)-ones via One-pot Three-component Reaction in Aqueous Medium. Heterocycl. lett. 2013, 3, 359–369; (b) Kiyani, H.; Ghorbani, F. Efficient Tandem Synthesis of a Variety of Pyranannulated Heterocycles, 3,4-disubstituted isoxazol-5(4H)-ones, and α,β-unsaturated Nitriles Catalyzed by Potassium Hydrogen Phthalate in Water. Res. Chem. Intermed. 2015,41, 7847–7882.
   Google Scholar
• (a) Kiyani, H.; Ghorbani, F. Synthesis of Arylmethylideneisoxazol-5(4H)-ones in Water Catalyzed by Sodium Citrate. Heterocycl. lett. 2013, 3, 359–369; (b) 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.
   Google Scholar
• (a) 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; (b) Vaidya, S.P.; Shridhar, G.; Ladage S.; Ravishankar L. A Facile Synthesis of Isoxazolone Derivatives Catalyzed by Cerium Chloride Heptahydrate in Ethyl Lactate as a Solvent: A Green Methodology. Curr. Green Chem. 2016,3, 160–167. doi: 10.5012/bkcs.2011.32.10.3559
   Web of Science ®Google Scholar
• (a) Kiyani, H.; Ghorbani, F. Potassium Phthalimide as Efficient Basic Organocatalyst for the Synthesis of 3,4-disubstituted Isoxazol-5(4H)-ones in Aqueous Medium, J. Saudi Chem. Soc. 2017, 21, S112–S119; (b) Rikani, A.B.; Setamdideh, D. One-pot and Three-component Synthesis of Isoxazol-5(4H)-one Derivatives in the Presence of Citric Acid. Orient Chem. 2016,32, 1433–1437. doi: 10.1016/j.jscs.2013.11.002
   Web of Science ®Google Scholar
• (a) Zarnegar, Z.; Safari, J. A Highly Efficient Magnetic Solid Acid Catalyst for Synthesis of 2,4,5-trisubstituted Imidazoles Under Ultrasound Irradiation. Ultrason. Sonochem. 2013, 20, 740–746; (b) Zarnegar, Z.; Safari, J.; Mansouri Kafroudi, Z. Co3O4–CNT Nanocomposites: A Powerful, Reusable, and Stable Catalyst for Sonochemical Synthesis of Polyhydroquinolines. New J. Chem. 2015,39, 1445–1451. (c) Liu, Q.; Ai, H.; Li, Z. Potassium Sorbate as an Efficient and Green Catalyst for Knoevenagel Condensation. Ultrason. Sonochem. 2011,18, 477–479; (d) Liu, Q.; Ai, H.M. Sodium Benzoate as a Green, Efficient, and Recyclable Catalyst for Knoevenagel Condensation. Synth. Commun. 2012,42, 3004–3010; (e) Liu, Q.; Ai, H.-M.; Feng, S. Ultrasound-assisted Synthesis of Acylals from Aldehydes Using Mg(CH3SO3)2–HOAC. Synth. Commun. 2012,42, 122–127. doi: 10.1016/j.ultsonch.2012.10.004
   PubMed Web of Science ®Google Scholar
• (a) Ramazani, A.; Rouhani, M.; Joo, S.W. Novel, Fast and Efficient One-pot Sonochemical Synthesis of 2-aryl-1,3,4-oxadiazoles. Ultrason. Sonochem. 2014, 21, 262–267; (b) Ramazani, A.; Rouhani, M.; Joo, S.W. Catalyst-free Sonosynthesis of Highly Substituted Propanamide Derivatives in Water. Ultrason. Sonochem. 2016,28, 393–399; (c) Rouhani, M.; Ramazani, A.; Joo, S.W. Ultrasonics in Isocyanide-based Multicomponent Reactions: A New, Efficient and Fast Method for the Synthesis of Fully Substituted 1,3,4-oxadiazole Derivatives Under Ultrasound Irradiation. Ultrason. Sonochem. 2015,22, 391–396; (d) Ahankar, H.; Ramazani, A.; Ślepokura, K.; Lis, T.; Joo, S.W. Synthesis of Pyrrolidinone Derivatives from Aniline, an Aldehyde and Diethyl Acetylenedicarboxylate in an Ethanolic Citric Acid Solution Under Ultrasound Irradiation. Green Chem. 2016,18, 3582–3593. doi: 10.1016/j.ultsonch.2013.06.009
   PubMed Web of Science ®Google Scholar
• Zarnegar, Z.; Alizadeh, R.; Ahmadzadeh, M.; Safari, J. C–N Bond Formation in Alicyclic and Heterocyclic Compounds by Amine-modified Nanoclay. J. Mol. Struct. 2017, 1144, 58–65. doi: 10.1016/j.molstruc.2017.05.004
   Web of Science ®Google Scholar
• Lei, Z.; Ma, G.; Jia, C. Montmorillonite (MMT) Supported Tin (II) Chloride: An Efficient and Recyclable Heterogeneous Catalyst for Clean and Selective Baeyer–Villiger Oxidation with Hydrogen Peroxide. Catal. Commun. 2007, 8, 305–309. doi: 10.1016/j.catcom.2006.05.045
   Web of Science ®Google Scholar
• Breen, C.; Molloy, K.C.; Quill, K. Mossbauer Spectroscopic and Thermogravimetric Studies of Tin-clay Complexes. Clay Miner. 1992, 27, 445–455. doi: 10.1180/claymin.1992.027.4.05
   Web of Science ®Google Scholar