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Title: Synthesis and applications of 4N-substituted oxazoles
Author: Gillie, Andrew Duncan
ISNI:       0000 0004 5370 8694
Awarding Body: University of Birmingham
Current Institution: University of Birmingham
Date of Award: 2015
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This thesis describes the advancement of a flexible and convergent gold-catalysed synthesis of trisubstituted oxazoles, and its application to the synthesis of novel polycyclic compounds. Following on from the initial discovery of this reaction, its scope and limitations have been have been explored, leading to a significant increase in the range of functionality which can be incorporated into the products. This reaction, and the novel structure of the 4-amido oxazole products, was then exploited to allow the construction of other complex molecules. A one-pot reaction cascade has been developed, in which the oxazole formation is followed by an intramolecular Diels-Alder reaction, allowing the rapid construction of polyheterocyclic compounds from simple starting materials. Finally, the synthesis of the first oxazole-annulated imidazolium salts is described. These salts act as precursors to prochiral nucleophilic heterocyclic carbene ligands, the organometallic chemistry of which has been investigated.
Supervisor: Not available Sponsor: Engineering and Physical Sciences Research Council (EPSRC) ; University of Birmingham
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: QD Chemistry