Physical Sciences and Mathematics Commons^™

Synthesis Of Oxyquinoliziniporphyrins And Pyridoquinoliziniporphyrins, Emma Cramer

Theses and Dissertations

N-confused porphyrins are porphyrin analogues that introduce a nitrogen outside of the macrocyclic cavity. Two novel N-confused type porphyrins were targeted for this study. Both syntheses use the key intermediate 4-quinolizone. Previous studies of N-confused pyriporphyrin showed that the system is nonaromatic and resembles structurally analogous benziporphyrins. However, modifications to systems of this type can introduce aromatic characteristics. The first system targeted introduced a quinolizone subunit into a porphyrin system. Quinolizone contains a thermodynamically stable amide and this unit disrupts the aromatic pathway. However, dipolar resonance contributors can potentially reinstate some aromatic character. A quinolizone dialdehyde was condensed with tripyrranes …