Use of 1-pentafluorosulfanyl-phenylacetylenes for the preparation of SF5-substituted five-membered ring heterocycles through 1,3-dipolar cycloadditions. Isoxazoles and isoxazolines

• Published in: Journal of fluorine chemistry Vol. 176; pp. 121 - 126
• Main Authors: Lopez, Simon E., Mitani, Akira, Pena, Priscila, Ghiviriga, Ion, Dolbier, William R.
• Format: Journal Article
• Language: English
• Published: LAUSANNE Elsevier B.V 01.08.2015; Elsevier
• Subjects: 1,3-Dipolar cycloaddition; Aryl SF5-acetylenes; Chemistry; Chemistry, Inorganic & Nuclear; Chemistry, Organic; Isoxazole; Isoxazoline; Pentafluorosulfanyl; Physical Sciences; Science & Technology; Isoxazole; 1,3-Dipolar cycloaddition; Pentafluorosulfanyl; Aryl SF5-acetylenes; Isoxazoline; LEAD OPTIMIZATION; SUBSTITUENTS; BENZISOXAZOLES; POTENT INHIBITORS; FALCIPARUM DIHYDROOROTATE DEHYDROGENASE; BIOLOGICAL EVALUATION; CHEMISTRY; FLUORINE; DERIVATIVES; EFFICIENT
• ISSN: 0022-1139; 1873-3328
• DOI: 10.1016/j.jfluchem.2015.06.006

1,3-Dipolar cycloadditions of nitrile oxides and nitrones with SF5-substituted alkynes. •1,3-Dipolar cycloadditions of nitrile oxides and nitrones are reported.•SF5-substituted alkynes are used in 1,3-dipolar cycloaddition reactions.•Preparations of SF5-substituted isoxazoles and isoxazolines are reported. A synthetic methodology utilizing 1,3-dipolar cycloadditions was developed for the preparation of pentafluorosulfanyl-substituted heterocycles using SF5-substituted arylacetylenes as key building block dipolarophiles. A group of 4-SF5-isoxazoles were prepared in moderate yields using in situ generated nitrile oxides, and 4-SF5-substituted isoxazolines were obtained when nitrones were used as the 1,3-dipole.