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Development of a One Pot [4+2]/r[4+2] 2-Pyridone Synthesis and the Fluorescence of 2-Pyridone Azafluorenones

Angello, Nicholas
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.
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2018-01-01
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Angello_wmgrad_0261N_10305.pdf
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Scheerer, Jonathan R
Abelt, Christopher J
Hinkle, Robert J
Department
Chemistry
DOI
http://dx.doi.org/10.21220/s2-s0ga-cq17
URI
https://scholarworks.wm.edu/handle/internal/8874
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