Palladium- and copper-catalysed heterocycle synthesis
<p>A number of privileged starting materials based on aryl halide frameworks have emerged that allow access to a variety of different heterocyclic scaffolds through judicious choice of reaction conditions. This work describes efforts to develop and extend th...
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| Formaat: | Thesis |
| Taal: | English |
| Gepubliceerd in: |
2014
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| Samenvatting: | <p>A number of privileged starting materials based on aryl halide frameworks have emerged that allow access to a variety of different heterocyclic scaffolds through judicious choice of reaction conditions. This work describes efforts to develop and extend the utility of two of these general heterocycle precursors - <em>ortho</em>-(haloalkenyl)aryl halides A and α-(<em>ortho</em>-haloaryl) ketones B - in conjunction with cascade reactions involving the construction of key carbon-heteroatom bonds <em>via</em> palladium or copper catalysis.</p> <p>Chapter 1 entails an overview of the development of palladium- and copper-catalysed carbon-heteroatom bond forming processes. The application of these processes in heterocycle synthesis using <em>ortho</em>-(haloalkenyl)aryl halide and <em>ortho</em>-haloacetanilides/ α-(<em>ortho</em>-haloaryl) ketone precursors is also described.</p> <p>Chapter 2 focuses on the development of a two-step synthesis of cinnolines using <em>ortho</em>-(haloalkenyl)aryl halides via intermediate protected dihydrocinnoline derivatives C.</p> <p>Chapter 3 demonstrates how the inherent reactivity of protected dihydrocinnoline derivatives C can be harnessed to provide access to functionalised products. A brief target synthesis of a pharmaceutically-relevent cinnoline is also described.</p> <p>Chapter 4 details attempts to develop a novel synthesis of benzothiophenes D from both <em>ortho</em>-(haloalkenyl)aryl halide and α-(<em>ortho</em>-haloaryl) ketone precursors.</p> |
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