Date of Award

2022

Document Type

Masters Thesis

Degree Name

M.S.

Organizational Unit

College of Natural Science and Mathematics, Chemistry and Biochemistry

First Advisor

Andrei G. Kutateladze

Second Advisor

Brian Michel

Third Advisor

John Latham

Fourth Advisor

Scott Barbee

Keywords

Organic synthesis, Photoassisted synthesis, Photochemistry

Abstract

Benozoxazinones have long been of interest to agrochemical scientists and medicinal chemists because of their widespread biological activity. These scaffolds are also of interest to synthetic chemists, who recognize the utility of benzoxazinones for accessing functionalized heterocycles. The use of efavirenz, a benzoxazinone-based reverse transcriptase inhibitor used in the treatment of HIV-1, has brought increased attention to this privileged pharmacophore. While there exist numerous strategies for synthesizing benzoxazinones, methods that do not require the use of acutely toxic and environmentally hazardous reagents are lacking. Consequently, there is a need to develop new methods for constructing this valuable scaffold. Herein, we report a photochemical alkyne migration that provides rapid access to the benzoxazinone scaffold. This is the first reported photochemical synthesis of a benzoxazinone, and, to our knowledge, the first reported photochemical alkyne migration.

Publication Statement

Copyright is held by the author. User is responsible for all copyright compliance.

Rights Holder

Andrés G. Muñoz

Provenance

Received from ProQuest

File Format

application/pdf

Language

en

File Size

129 pgs

Discipline

Organic chemistry

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