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Domino Reactions Involving Merged Cycloaddition and Cycloreversion Processes Affording Pyridine Products

Williamson, Jill
Abstract
This thesis explores oxazinone and pyrazinone intermediates in the merged Diels-Alder and retro-Diels-Alder strategies for the synthesis of substituted pyridines. Dihydrooxazinone substrates are prepared and investigated in a domino reaction sequence that comprises an aldol condensation, alkene isomerization, Diels-Alder, and retro-Diels-Alder reaction. Preliminary efforts intended to expand the reaction scope to include aliphatic aldehydes are included and potentially applicable to the synthesis of guaipyridine alkaloids including the rupestines.
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2016-04-01
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Undergraduate Honors Theses
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Advisor
Scheerer, Jonathan
Abelt, Christopher
Harbron, Elizabeth
Kerscher, Oliver
Department
Chemistry
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https://scholarworks.wm.edu/handle/internal/12747
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