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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| स्वरूप: | थीसिस |
| भाषा: | English |
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2014
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| _version_ | 1826273689564348416 |
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| author | Ball, C |
| author2 | Willis, M |
| author_facet | Willis, M Ball, C |
| author_sort | Ball, C |
| collection | OXFORD |
| description | <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> |
| first_indexed | 2024-03-06T22:32:03Z |
| format | Thesis |
| id | oxford-uuid:589b70fb-0823-4ccf-8b35-1883908f917d |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T22:32:03Z |
| publishDate | 2014 |
| record_format | dspace |
| spelling | oxford-uuid:589b70fb-0823-4ccf-8b35-1883908f917d2022-03-26T17:04:30ZPalladium- and copper-catalysed heterocycle synthesisThesishttp://purl.org/coar/resource_type/c_db06uuid:589b70fb-0823-4ccf-8b35-1883908f917dHeterocyclic chemistryCatalysisOrganic chemistryOrganic synthesisChemistry & allied sciencesEnglishOxford University Research Archive - Valet2014Ball, CWillis, M<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> |
| spellingShingle | Heterocyclic chemistry Catalysis Organic chemistry Organic synthesis Chemistry & allied sciences Ball, C Palladium- and copper-catalysed heterocycle synthesis |
| title | Palladium- and copper-catalysed heterocycle synthesis |
| title_full | Palladium- and copper-catalysed heterocycle synthesis |
| title_fullStr | Palladium- and copper-catalysed heterocycle synthesis |
| title_full_unstemmed | Palladium- and copper-catalysed heterocycle synthesis |
| title_short | Palladium- and copper-catalysed heterocycle synthesis |
| title_sort | palladium and copper catalysed heterocycle synthesis |
| topic | Heterocyclic chemistry Catalysis Organic chemistry Organic synthesis Chemistry & allied sciences |
| work_keys_str_mv | AT ballc palladiumandcoppercatalysedheterocyclesynthesis |