Date Awarded

2018

Document Type

Thesis

Degree Name

Master of Science (M.Sc.)

Department

Chemistry

Advisor

Jonathan R Scheerer

Committee Member

Christopher J Abelt

Committee Member

Robert J Hinkle

Abstract

We report the concise synthesis of several tricyclic 2-pyridones via a one pot sequence involving an aldol condensation, alkene isomerization, intramolecular Diels-Alder cycloaddition, and selective retro-Diels-Alder cycloreversion. The starting materials are synthesized in one step from cheap and commercially available precursors. The intermediate [2.2.2]diazabicycloalkene cycloadducts can be isolated. The retro-Diels-Alder occurs at easily accessible temperatures due to base acceleration. Simple derivatization of the tricyclic products afforded azafluorenones with unprecedented fluorescent activity due to the pyridone motif.

DOI

http://dx.doi.org/10.21220/s2-s0ga-cq17

Rights

© The Author

Available for download on Sunday, October 11, 2020

Included in

Chemistry Commons

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