Chapter 1 is a literature review of selected palladium-catalysed aryl C-N and C-S bond forming reactions. The application of these reactions to the synthesis of heterocycles is also discussed. Chapter 2 highlights the importance of the benzimidazole motif and gives a brief discussion of the existing routes to this scaffold. The utility of N-(o-halophenyl)imidoyl chlorides and imidates as precursors to heterocycles is demonstrated in a palladium-catalysed reaction with N-nucleophiles to afford benzimidazole products. Chapter 3 provides a brief introduction to the synthesis of benzothiazoles and describes efforts towards the use of our established substrates for the preparation of these heterocycles. This is achieved via reaction of N-(o-chlorophenyl)imidoyl chlorides with a sulfur nucleophile in a metal-free process. Chapter 4 is a literature review of palladium-catalysed carbonylation chemistry with specific focus on aminocarbonylation and thiocarbonylation reactions of aryl halides. Heterocycle syntheses which employ such carbonylative methods are also discussed. Chapter 5 describes existing protocols for the synthesis of quinazolinones. A novel palladium-catalysed synthesis of these heterocycles from the reaction of our imidate substrates with an amine and carbon monoxide is described. This further demonstrates their utility as general heterocycle precursors
| Identifer | oai:union.ndltd.org:bl.uk/oai:ethos.bl.uk:581015 |
| Date | January 2012 |
| Creators | Sadig, Jessie E. R. |
| Contributors | Willis, Michael C. |
| Publisher | University of Oxford |
| Source Sets | Ethos UK |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
| Source | http://ora.ox.ac.uk/objects/uuid:c9608957-d215-4a15-87e3-5871c1391946 |
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