ESIPT-Enabled Alkyne Migration Provides Rapid Access to Benzoxazinones

<p>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.</p>

Name thesis:degree_name

M.S.

Level thesis:degree_level

Masters Thesis

Year dc:date.available

2022

Author dc:creator

• Muñoz, Andrés G.

Contributors dc:contributor

• Andrei G. Kutateladze
• Brian Michel
• John Latham
• Scott Barbee

• Organic synthesis
• Photoassisted synthesis
• Photochemistry
• Chemistry
• Organic Chemistry
• Other Chemistry

Statement dc:rights

• <p>Copyright is held by the author. User is responsible for all copyright compliance.</p>

Language dc:language

en

Repository record dc:identifier

https://digitalcommons.du.edu/etd/2148

OAI identifier oai:identifier

oai:digitalcommons.du.edu:etd-3135