Honors Theses

Date of Award

Spring 5-9-2020

Document Type

Undergraduate Thesis

Department

Chemistry and Biochemistry

First Advisor

Sudeshna Roy

Second Advisor

Gerald Rowland

Third Advisor

Susan Pedigo

Relational Format

Dissertation/Thesis

Abstract

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.

Creative Commons License

Creative Commons Attribution 4.0 License
This work is licensed under a Creative Commons Attribution 4.0 License.

Share

COinS
 
 

To view the content in your browser, please download Adobe Reader or, alternately,
you may Download the file to your hard drive.

NOTE: The latest versions of Adobe Reader do not support viewing PDF files within Firefox on Mac OS and if you are using a modern (Intel) Mac, there is no official plugin for viewing PDF files within the browser window.