Date of Award
Chemistry and Biochemistry
The presence of fluorine can provide organic compounds with useful biological properties, such as increased metabolic stability and drug uptake. Because of these advantages, fluorinated compounds make up about 30% of the drug industry. However, fluorination of complex molecules is difficult due to fluorine’s high electronegativity.
Fluorinated isoxazoles are of particular interest in the pharmaceutical industry. Isoxazoles are five-membered heterocycles with oxygen and nitrogen in the 1, 2 positions that are able to engage in interactions unavailable to other ring structures, conferring advantageous biological properties upon compounds containing them. However, there are limited synthetic routes for fluorinated isoxazoles, and those that have been reported in the past have poor yields and require harsh conditions.
In 2014, a gold-catalyzed cyclization-fluorination of O-methyl oximes to produce fluorinated isoxazole was reported. The goal of this project was to test synthetic routes of fluorinated isoxazoles that require less expensive materials, focusing on the synthesis of 4-fluoro-3,5-disubstituted isoxazole via a silver-catalyzed cyclization.
Stewart, Micah, "Silver-Catalyzed Synthesis of Disubstituted Fluorinated Isoxazoles" (2020). Honors Theses. 1444.
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