Date of Award
Chemistry and Biochemistry
Pyrazole-based pharmaceuticals treat a wide array of diseases and conditions including obesity, diabetes, cancer, microbial and viral infections, pain and inflammation, and many neurological disorders. Syntheses for this biologically significant substrate have been well developed, but current methods to afford fluorinated pyrazoles are limited by variability and selectivity. By 2013, over 25% of all drugs available on the market contained the element fluorine due to its unique characteristics leading to improved target protein binding, bioavailability, and metabolic stability. In order to harness these pharmaceutical benefits of fluorine and overcome its difficulty in handling and stability, we set out to develop new synthetic methods to afford fluorinated pyrazoles via intra- and intermolecular cyclization reactions. In this work, we demonstrate the utility of alpha-fluoronitroalkenes in regioselective intermolecular cyclization to afford 4-fluoropyrazoles.
Saucier, Matthew, "Synthesis of Fluorinated Pyrazoles via Intra- and Intermolecular Cyclization Reactions" (2020). Honors Theses. 1313.
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