Date of Award

1-1-2016

Document Type

Dissertation

Degree Name

Ph.D.

Department

Chemistry and Biochemistry

First Advisor

Andrei Kutateladze

Second Advisor

James Fogelman

Keywords

beta-lactams, Diversity Oriented Synthesis, hydantoins, o-azaxylylenes, Photochemistry, Polyheterocycles

Abstract

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 β-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.

Provenance

Recieved from ProQuest

Rights holder

Weston James Umstead

File size

123 p.

File format

application/pdf

Language

en

Discipline

Organic chemistry

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