Bioorg Chem 2021 Jun 8;114:105071. Epub 2021 Jun 8.
University of Monastir, Faculty of Science of Monastir, Laboratory of Heterocyclic, Chemistry, Natural Products and Reactivity, TeamMedicinal Chemistry and Natural, Products (LR11ES39), Department of Chemistry, Avenue of Environment, 5019 Monastir, Tunisia. Electronic address:
Two series of 3,5-disubstituted isoxazoles (6a-e) and 1,4-disubstituted triazoles (8a-e) derivatives have been synthesized from tyrosol (1), a natural phenolic compound, detected in several natural sources such as olive oil, and well-known by its wide spectrum of biological activities. Copper-catalyzed microwave-assisted 1,3-dipolar cycloaddition reactions between tyrosol-alkyne derivative 2 and two series of aryl nitrile oxides (5a-e) and azides (7a-e) regiospecifically afforded 3,5-disubstituted isoxazoles (6a-e) and 1,4-triazole derivatives (8a-e), respectively in quantitative yields. Synthesized compounds were purified and characterized by spectroscopic means including 1D and 2D NMR techniques and HRMS analysis. Read More