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Title: A carbenoid approach to functionalised heterocycles
Author: Honey, Mark A.
ISNI:       0000 0004 2720 0133
Awarding Body: University of Nottingham
Current Institution: University of Nottingham
Date of Award: 2011
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This Thesis describes the development of methodology towards an array of functionalised heterocycles from metal-catalysed carbenoid X-H insertion reactions. Chapter 1 introduces the concept of carbenoid chemistry, with carbenoid N- H, O-H and S-H insertion reactions being reviewed. Chapter 2 discusses various methods available for the synthesis of a- diazocarbonyl compounds, with the results and discussion section detailing the synthesis of numerous diazo-containing compounds which will be used throughout this Thesis. The introduction of Chapter 3 details selected literature examples of indole syntheses, with the results and discussion section detailing synthesis of indoles via a modified Bischler indole approach. Chapter 4 summarises selected literature examples of benzofuran and benzothiophene syntheses, with the results and discussion sections detailing a one-pot synthesis of benzofurans from phenols, and the attempted synthesis of benzothiophenes from benzenethiols. Chapter 5 details previous syntheses of both pyrimidines and pyrazoles, with the results and discussion section describing the synthesis of common intermediates derived from metal-catalysed N-H insertion reactions. These intermediates are then successfully utilised in the synthesis of a range of functionalised pyrimidiones and pyrazolones. Efforts towards the synthesis of trifluoromethyl-substituted heterocycles are detailed within Chapter 6, in which novel rhodium-catalysed N-H insertion reactions of ethyl 2-diazo-4,4,4-trifluoro-3-oxobutanoate are described, with the isolation of novel N-H insertion products, as well as the formation of a range of thiazoles, oxazoles a l,2,4-triazole and a pyridine. This Thesis concludes with specific details of experimental procedures and full characterisation data for compounds synthesised throughout the results and discussion sections of this Thesis.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available