Date Thesis Awarded
5-2024
Access Type
Honors Thesis -- Access Restricted On-Campus Only
Degree Name
Bachelors of Science (BS)
Department
Chemistry
Advisor
Jonathan Scheerer
Committee Members
Christopher Abelt
Tyler Meldrum
Jaclyn Moloney
Abstract
This project's purpose is to develop a new method of synthesizing oxazinones using widely available amino alcohol precursors. Oxazinones are fascinating and understudied heterocyclic ring systems that have their own respective importance, but are also reactive intermediates that lead to the production of pyridines. Pyridines are the second most common nitrogen-containing ring structure found in FDA approved therapeutic molecules such as anti-cancer and anti-malarial agents. Currently there are limited methods of synthesizing oxazinones that rely on harsh reaction conditions. We have developed a new method to prepare oxazinones derivatives from commercially available amino alcohol precursors, which has allowed for downstream conversion to pyridine structures of interest. So far, this project has seen success in the synthesis of seven oxazinones and their subsequent pyridine derivatives. Xylanigripone A, a molecule isolated from the Xylaria nigripes fungus that has tranquilizing effects on the central nervous system, was prepared using this chemistry. Future research will explore different amino alcohols precursors in the synthesis of oxazinones and applications toward synthesizing natural products containing the pyridine motif.
Recommended Citation
Shahla, Zannatul, "Synthesis of Pyridine Derivatives: Cycloaddition/Cycloreversion of 1,4-Oxazinone Intermediates" (2024). Undergraduate Honors Theses. William & Mary. Paper 2226.
https://scholarworks.wm.edu/honorstheses/2226
