Synthesis and applications of 4N-substituted oxazoles


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Gillie, Andrew Duncan (2015). Synthesis and applications of 4N-substituted oxazoles. University of Birmingham. Ph.D.

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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.

Type of Work: Thesis (Doctorates > Ph.D.)
Award Type: Doctorates > Ph.D.
College/Faculty: Colleges (2008 onwards) > College of Engineering & Physical Sciences
School or Department: School of Chemistry
Funders: Engineering and Physical Sciences Research Council, Other
Other Funders: The University of Birmingham
Subjects: Q Science > QD Chemistry


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