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Synthesis Of 3,4,5-Trisubstituted Isoxazoles In Water Via A [3 + 2]-Cycloaddition Of Nitrile Oxides And 1,3-Diketones, Β-Ketoesters, Or Β-Ketoamides, Md Imran Hossain, Md Imdadul H. Khan, Seong Jong Kim, Hoang V. Le
Synthesis Of 3,4,5-Trisubstituted Isoxazoles In Water Via A [3 + 2]-Cycloaddition Of Nitrile Oxides And 1,3-Diketones, Β-Ketoesters, Or Β-Ketoamides, Md Imran Hossain, Md Imdadul H. Khan, Seong Jong Kim, Hoang V. Le
Faculty and Student Publications
Herein we report a method for the synthesis of 3,4,5-trisubstituted isoxazoles in water under mild basic conditions at room temperature via a [3 + 2]-cycloaddition of nitrile oxides and 1,3-diketones, β-ketoesters, or β-ketoamides. We optimized the reaction conditions to control the selectivity of the production of isoxazoles and circumvent other competing reactions, such as O-imidoylation or hetero [3 + 2]-cycloaddition. The reaction happens fast in water and completes within 1-2 hours, which provides an environmentally friendly access to 3,4,5-trisubstituted isoxazoles, an important class of structures found in numerous bioactive natural products and pharmaceuticals. Additionally, we optimized the reaction conditions to …