Date of Award
2022
Document Type
Thesis
Degree Name
M.S.
Department
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.
Recommended Citation
Muñoz, Andrés G., "ESIPT-Enabled Alkyne Migration Provides Rapid Access to Benzoxazinones" (2022). Electronic Theses and Dissertations. 2148.
https://digitalcommons.du.edu/etd/2148
Provenance
Received from ProQuest
Rights holder
Andrés G. Muñoz
File size
129 pgs
Copyright date
2022
File format
application/pdf
Language
en
Discipline
Organic chemistry