Physical Sciences and Mathematics Commons^™

Synthesis Of Fluorinated Pyrazoles Via Intra- And Intermolecular Cyclization Reactions, Matthew Saucier

Honors Theses

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 …

Silver-Catalyzed Synthesis Of Disubstituted Fluorinated Isoxazoles, Micah Stewart

Honors Theses

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 …

A Study To Regioselectively Access Fluorinated Triazoles And Isoxazoles, Sweta Adhikari

Electronic Theses and Dissertations

The objective of the thesis is to develop regioselective methods for mono-fluorination of disubstituted triazoles, both 1,4- and 1,5-regioisomer, and isoxazoles. These strategies focus on one-pot direct access to final mono-fluorinated triazoles and isoxazoles. Eventually, these fluorinated substrates will be screened against various biological targets. Similarly, the optimization study of a regioselective method to generate 5-fluoro-1,4-disubstituted triazole was conducted. This reaction also utilized 1,3-dipolar cycloaddition to synthesize fluorinated triazole. However, difluoroalkene was used as a synthetic equivalent of fluoroalkyne for this method. This resulted into the inversion of polarity affording a different regioisomer. Here, fluoronitroalkene was identified as a synthetic …