Synthesis and Characterization of the Novel Heterocyclic Ring System: dihydropyrimido quinolin-one
Gottler, Lindsey M.
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The initial goal ofthe research project was to reproduce the preliminary results by resynthesizing the novel ring system 3-(benzyl)-7-fluoro-l-[(lZ,3Z)-1 ,3-pentadienyl]-2,3dihydropyrimido[ 5,4-c]quinolin-4(lH)-one. Once reproducibility was achieved, optimization ofthe reaction was studied. The parameters in question were the reaction time, temperature and the solvent system. The optimization ofthe reaction then allowed for full characterization ofthe final product. In addition, by monitoring the reaction during optimization the reaction mechanism ofthe transformation was explored. The final goal was then to consider various substituents on the benzyl group attached to the amide nitrogen. Specifically, a para-bromo and a nitro group were favored for added mass and electron density in comparison to the original para-chloride previously prepared. The addition ofthe heavier bromide atom was anticipated to improve upon xray crystallography data. Alternatively, the nitro group may impart improved crystallinity and perhaps higher quality crystal structures would be available. During the initial preparations ofthe dihydropyrimido quinolinone crystal structures were obtained revealing a four-molecule arrangement per cell. The p-bromo product resulted in increased crystal quality and similar crystal arrangement. The p-nitro product was unable to be crystallized with using the acetonitrile solvent system.