Development of a One Pot [4+2]/r[4+2] 2-Pyridone Synthesis and the Fluorescence of 2-Pyridone Azafluorenones
Master of Science (M.Sc.)
Jonathan R Scheerer
Christopher J Abelt
Robert J Hinkle
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.
© The Author
Angello, Nicholas, "Development of a One Pot [4+2]/r[4+2] 2-Pyridone Synthesis and the Fluorescence of 2-Pyridone Azafluorenones" (2018). Dissertations, Theses, and Masters Projects. William & Mary. Paper 1550153876.