Date of Award
Chemistry and Biochemistry
Andrei Kutateladze, Ph.D.
James Fogelman, Ph.D.
Beta-Lactams, Diversity Oriented Synthesis, Hydantoins, o-azaxylylenes, Photochemistry, Polyheterocycles
This research set out to continue the exploration and diversification of excited state o-azaxylylene cycloadditions, utilizing both pre-photochemical and post-photochemical modifications.
Pre-photochemical modifications came through the addition of heteroatoms, namely nitrogen and oxygen, to the tether that links the unsaturated photopendant to the photogenerated o-azaxylylene. Photochemistry resulted in the formation of new, interesting N, O, S polyheterocycles.
Post-photochemical modifications took place through several different cycloaddition reactions, including a [4+2] hetero-Diels Alder reaction, a [4+2] Povarov cyclization, a [3+2] nitrile oxide addition, and a [3+2] nitrone cyclization. These reactions were applied first to a model system, and then to a new scaffold that contained the biologically relevant beta-lactam fragment.
A summation of engineering work is also included to detail the development and implementation of several new LED irradiators. These irradiators are key to the photochemistry that will be discussed, and their development will serve as a blueprint for future work and improvement.
Copyright Statement / License for Reuse
This work is licensed under a Creative Commons Attribution 4.0 License.
Umstead, Weston James, "Photoassisted Generation of Complex N, O, S Polyheterocycles" (2016). Electronic Theses and Dissertations. 1117.
Received from ProQuest
Weston James Umstead