Functionalization of pyridines and other azines via phosphorus ligand-coupling reactions
| dc.contributor.author | Hilton, Michael C., author | |
| dc.contributor.author | McNally, Andrew, advisor | |
| dc.contributor.author | Reynolds, Melissa, committee member | |
| dc.contributor.author | Crans, Debbie, committee member | |
| dc.contributor.author | Montgomery, Tai, committee member | |
| dc.date.accessioned | 2020-01-13T16:41:55Z | |
| dc.date.available | 2020-01-13T16:41:55Z | |
| dc.date.issued | 2019 | |
| dc.description.abstract | Nitrogen heterocycles are ubiquitous in pharmaceutical compounds with pyridine being one of the most frequently occurring examples. The discovery and development of new drugs rely heavily on our ability to modify these commonly occurring structures. The functionalization of pyridine has a long history but despite this, there remain some deficiencies in this area of synthesis. Reactions which expand upon the known methodologies are of tremendous value to medicinal chemists who frequently work with pyridines and similar azines. Chapter one will cover the relevance of pyridines in pharmaceuticals and will explain how structural features contribute to their presence in drugs. Conventional and newer methods to functionalize pyridine are also addressed. Chapter two will describe the work of the McNally lab in the development of heterocyclic phosphonium salts as reagents to selectively functionalize pyridines. An application of these salts is as precursors to form C−O bonds from alkoxide nucleophiles. Chapter three presents the development of a strategy to construct bis-heterobiaryls using phosphorus ligand-coupling. This method offers an alternative to the widely used metal-catalyzed approaches which often struggle in the synthesis of bis-heterobiaryls. Lastly, chapter four will expand upon this work showing a new approach to prepare bis-heterobiaryls using heteroaryl halides. This route enables easy access to 2,2'-bipyridines which are difficult to synthesize using conventional methods. | |
| dc.format.medium | born digital | |
| dc.format.medium | doctoral dissertations | |
| dc.identifier | Hilton_colostate_0053A_15786.pdf | |
| dc.identifier.uri | https://hdl.handle.net/10217/199813 | |
| dc.language | English | |
| dc.language.iso | eng | |
| dc.publisher | Colorado State University. Libraries | |
| dc.relation.ispartof | 2000-2019 | |
| dc.rights | Copyright and other restrictions may apply. User is responsible for compliance with all applicable laws. For information about copyright law, please see https://libguides.colostate.edu/copyright. | |
| dc.title | Functionalization of pyridines and other azines via phosphorus ligand-coupling reactions | |
| dc.type | Text | |
| dcterms.rights.dpla | This Item is protected by copyright and/or related rights (https://rightsstatements.org/vocab/InC/1.0/). You are free to use this Item in any way that is permitted by the copyright and related rights legislation that applies to your use. For other uses you need to obtain permission from the rights-holder(s). | |
| thesis.degree.discipline | Chemistry | |
| thesis.degree.grantor | Colorado State University | |
| thesis.degree.level | Doctoral | |
| thesis.degree.name | Doctor of Philosophy (Ph.D.) |
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