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Title: Synthesis and properties of pyrrolizin-3-ones and their aza analogues
Author: Thornley, Craig
Awarding Body: University of Edinburgh
Current Institution: University of Edinburgh
Date of Award: 1993
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A number of novel pyrrolizin-3-ones and azapyrrolizinones have been prepared by flash vacuum pyrolysis. The pyrolysis of azole Meldrum's acid derivatives has been extended to the synthesis of several substituted pyrrolizin-3-ones and pyrrolo[1,2-c]imidazol-5-ones. A second route to these heterocycles and the pyrrolo[1,2,-a]imidazol-5-one system involves the pyrolysis of readily accessible azolylpropenoic acid esters; the crystal structures of several of the propenoates are reported. The new methodology overcomes several drawbacks associated with the previous route; the mechanism of the reaction has also been investigated. The reactions of pyrrolizin-3-ones, pyrrolo[1,2-a]imidazol-5-one and pyrrolo[1,2-c]imidazol-5-one with a number of nucleophiles have been studied. In addition, the reactions of pyrrolizin-3-one with electrophiles, free radicals and enophiles are discussed. The reactivity of these systems is dominated by their olefinic and N-acyl functionality. The findings of the above studies have been applied to the synthesis of 5,7a-didehydroheliotridin-3-one, a partially reduced pyrrolizin-3-one present in a number of pyrrolizidine alkaloids. The structure and spectroscopic properties of the pyrrolizin-3-ones, pyrrolo[1,2-a]imidazol-5-ones and pyrrolo[1,2-c]imidazol-5-ones, and some dihydro derivatives, obtained during the course of this study are discussed.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available