Eric Fossum (Committee Member), Andrew Hsu (Other), Daniel Ketcha (Committee Member), Kenneth Turnbull (Committee Chair)
Master of Science (MS)
In the present work, the reactivity of alkyl and aryl sydnoquinoxalines was studied. Using a previously developed method, triphenylphosphine-2-(3-sydnonyl)phenylimide was prepared in a two-step process via a diazotization / azidation process of 3-(2-aminophenyl)sydnone, followed by treatment with triphenylphosphine. Due to the inability to achieve previously reported yields, a new, one-step method using Mitsunobu conditions was employed to synthesize the iminophosphorane in a good yield. A similar, brominated iminophosphorane was synthesized using the same conditions in a good yield. Treatment of both the brominated and non-brominated iminophosphoranes with alkyl and aryl isocyanates or isothiocyanates in an aza-Wittig process, gave the corresponding alkyl or aryl sydnoquinoxalines. Deprotection of 4-(tert-butylamino)sydno[3,4-a]quinoxaline led to a putative amino sydnoquinoxaline. Reactions with certain anhydrides were successful, however, reactions with sulfonyl chlorides and acid chlorides were not per the expectations.
Additionally, the utility of halogenated fused-ring sydnones for Sonogashira coupling reactions has been explored. Coupling reactions of both bromo and iodo sydnones are discussed. Chemoselective reaction of an iodine over a bromine in a dihalogenated sydnoquinoxaline has been studied, and is discussed.
Department or Program
Department of Chemistry
Year Degree Awarded
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