A one-pot synthesis of 3-trifluoromethyl-2-isoxazolines from trifluoromethyl aldoxime

Scholarly Works

• Ghodile, N. G.; Bhade, M. W. Synthesis and Characterization of Some Chlorosubstituted Azoles and their Screening Against Some Mushroom Crop Pathogens and Study of their Efficacy on Growth of Oyster Mushroom spp. Current Agriculture Research Journal 2024, 11, 955–960. doi:10.12944/carj.11.3.24
• Youssefi, Y.; Ansari, A.; Ou-ani, O.; Oucheikh, L.; Oubair, A.; Lgaz, H.; Hammouti, B.; Chaouiki, A.; Ko, Y. G.; Znini, M. Insights into the Corrosion Inhibition Performance of Three 2-Isoxazoline-γ-Lactones for Carbon Steel in Acidic Medium: Linking Molecular and Experimental-Level Information with Microscopic-Scale Modeling. Lubricants 2023, 11, 141. doi:10.3390/lubricants11030141
• Sydhulua, R.; Hemasria, Y. Synthesis of Novel Isoxazoline/Isoxzolyl Pyrano Heterocyclic Annulated Flavones. Asian Journal of Chemistry 2023, 35, 624–628. doi:10.14233/ajchem.2023.27286
• Mineyeva, I. V. α,β-Unsaturated β-Methyl-δ-lactones in Nitrile Oxide Cycloaddition Reactions. Synthesis of Saturated Lactones and Lactams. Russian Journal of Organic Chemistry 2022, 58, 765–779. doi:10.1134/s1070428022060033
• Motiwala, H. F.; Armaly, A. M.; Cacioppo, J. G.; Coombs, T. C.; Koehn, K. R. K.; Norwood, V. M.; Aubé, J. HFIP in Organic Synthesis. Chemical reviews 2022, 122, 12544–12747. doi:10.1021/acs.chemrev.1c00749
• Cordero, F. M.; Giomi, D.; Machetti, F. 4.03 – Isoxazoles. Comprehensive Heterocyclic Chemistry IV; Elsevier, 2022; Vol. 4, pp 308–434. doi:10.1016/b978-0-12-818655-8.00135-9
• Pajkert, R.; Koroniak, H.; Kafarski, P.; Röschenthaler, G.-V. Hypervalent-iodine mediated one-pot synthesis of isoxazolines and isoxazoles bearing a difluoromethyl phosphonate moiety. Organic & biomolecular chemistry 2021, 19, 4871–4876. doi:10.1039/d1ob00685a
• Kiss, L.; Benke, Z.; Nonn, M.; Remete, A. M.; Fustero, S. Diversity-Oriented Synthesis of Highly Functionalized Alicycles across Dipolar Cycloaddition/Metathesis Reaction. Synlett 2021, 32, 1911–1933. doi:10.1055/s-0040-1706041
• Wan, C.; Pang, J.-Y.; Jiang, W.; Zhang, X.; Hu, X.-G. Copper-Catalyzed Reductive Ring-Cleavage of Isoxazoles: Synthesis of Fluoroalkylated Enaminones and Application for the Preparation of Celecoxib, Deracoxib, and Mavacoxib. The Journal of organic chemistry 2021, 86, 4557–4566. doi:10.1021/acs.joc.0c02980
• Palchykov, V. A.; Gaponov, A. A. 1,3-Amino alcohols and their phenol analogs in heterocyclization reactions. Advances in Heterocyclic Chemistry; Elsevier, 2020; Vol. 131, pp 285–350. doi:10.1016/bs.aihch.2019.06.001
• Chalyk, B. A.; Khutorianskyi, A.; Lysenko, A.; Fil, Y. V.; Kuchkovska, Y. O.; Gavrilenko, K. S.; Bakanovych, I.; Moroz, Y. S.; Gorlova, A. O.; Grygorenko, O. O. Regioselective Synthesis of Functionalized 3- or 5-Fluoroalkyl Isoxazoles and Pyrazoles from Fluoroalkyl Ynones and Binucleophiles. The Journal of organic chemistry 2019, 84, 15212–15225. doi:10.1021/acs.joc.9b02258
• Chen, Y.; Li, L.; He, X.; Li, Z. Four-Component Reactions for the Synthesis of Perfluoroalkyl Isoxazoles. ACS Catalysis 2019, 9, 9098–9102. doi:10.1021/acscatal.9b03189
• Lopes, L. D.; Bortoluzzi, A. J.; Prampolini, G.; dos Santos, F. P. E.; Livotto, P. R.; Merlo, A. A. Structural and morphological aspects of small 3,5-disubstituted isoxazoles. Journal of Fluorine Chemistry 2018, 211, 24–36. doi:10.1016/j.jfluchem.2018.04.007
• Bonacorso, H. G.; Ketzer, A.; Rosa, W. C.; Calheiro, T. P.; Rodrigues, M. B.; Zanatta, N.; Martins, M. A. P.; Frizzo, C. P. Useful approach for O-functionalization of trifluoromethyl-substituted spirotetracyclic isoxazolines, and their application in the synthesis of 1,2,3-triazole derivatives. Journal of Fluorine Chemistry 2018, 210, 142–148. doi:10.1016/j.jfluchem.2018.03.012
• Wang, Q.; Tsui, G. C. Copper-Mediated Domino Cyclization/Trifluoromethylation of Propargylic N-Hydroxylamines: Synthesis of 4-Trifluoromethyl-4-isoxazolines. The Journal of organic chemistry 2018, 83, 2971–2979. doi:10.1021/acs.joc.7b03191
• Khutorianskyi, A.; Chalyk, B. A.; Borysko, P.; Kondratiuk, A.; Mykhailiuk, P. K. Difluoromethyl Nitrile Oxide (CF2HCNO): A Neglected Chemical Reagent. European Journal of Organic Chemistry 2017, 2017, 3935–3940. doi:10.1002/ejoc.201700764
• Mlostoń, G.; Kowalski, M. K.; Obijalska, E.; Heimgartner, H. Efficient synthesis of fluoroalkylated 1,4,2-oxathiazoles via regioselective [3 + 2]-cycloaddition of fluorinated nitrile oxides with thioketones. Journal of Fluorine Chemistry 2017, 199, 92–96. doi:10.1016/j.jfluchem.2017.04.011
• Bonacorso, H. G.; Ketzer, A.; Garcia, F. D.; Rosa, W. C.; Calheiro, T. P.; Feitosa, S. C.; Dal Forno, G. M.; Zanatta, N.; Martins, M. A. P.; Frizzo, C. P. Efficient approach for regioselective synthesis of new trifluoromethyl-substituted spirotetracyclic isoxazolines and isoxazoles. Journal of Fluorine Chemistry 2017, 197, 6–14. doi:10.1016/j.jfluchem.2017.02.004
• Kumar, V.; Kaur, K. Fluorinated isoxazolines and isoxazoles: A synthetic perspective. Journal of Fluorine Chemistry 2015, 180, 55–97. doi:10.1016/j.jfluchem.2015.09.004
• Pérez, J. M.; Ramón, D. J. Synthesis of 3,5-Disubstituted Isoxazoles and Isoxazolines in Deep Eutectic Solvents. ACS Sustainable Chemistry & Engineering 2015, 3, 2343–2349. doi:10.1021/acssuschemeng.5b00689

Explore citations to this article at