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New strategies to synthesize complex pyridines and tetrahydropyridines using main group chemistry

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dc.contributor.authorFricke, Patrick J., author
dc.contributor.authorMcNally, Andrew, advisor
dc.contributor.authorCrans, Debbie, committee member
dc.contributor.authorChen, Eugene, committee member
dc.contributor.authorKipper, Matthew, committee member
dc.date.accessioned2022-01-07T11:30:09Z
dc.date.available2024-01-06T11:30:09Z
dc.date.issued2021
dc.description.abstractPyridine and piperidine are important molecular scaffolds in small molecule drug development in medicinal chemistry research. Because of their importance, methods to synthesize complex pyridines and piperidines are highly desirable. Chapter one discusses the importance of these scaffolds in the pharmaceutical industry along with the history of pyridine and piperidine synthesis and the challenges that still remain. Chapter two discusses the switching strategies for selective installation of phosphonium salts on polyazines. The methods include an acylation, base-mediate, phosphine mediate, and order-of-reagent addition strategies. Additionally, we demonstrate how these methods can be applied to medicinal chemistry research during structure-activity relationship studies by derivatizing the phosphonium salts. Chapter three presents a new strategy for selective pyridine alkylation at the 4-position of the pyridine ring. Using a triazine chloride activating group allows for 4-selective phosphonium ylide formation inside the pyridine ring. A Wittig olefination-rearomatization sequence with an aldehyde then furnishes the alkylated pyridine. This method offers an alternative strategy to conventionally used metal-catalyzed cross coupling and Minisci-type reactions. Chapter four describes a stepwise reduction method for the synthesis of dihydropyridine and tetrahydropyridine. Using N-Tf activation allows for a selective hydride reduction to the dihydropyridine, which can subsequently undergo hydrogenation to the tetrahydropyridine.
dc.format.mediumborn digital
dc.format.mediumdoctoral dissertations
dc.identifierFricke_colostate_0053A_16828.pdf
dc.identifier.urihttps://hdl.handle.net/10217/234243
dc.languageEnglish
dc.language.isoeng
dc.publisherColorado State University. Libraries
dc.relation.ispartof2020-
dc.rightsCopyright 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.subjectphosphonium
dc.subjectpiperidine
dc.subjectylide
dc.subjectphosphorus
dc.subjecthydrogenation
dc.subjectpyridine
dc.titleNew strategies to synthesize complex pyridines and tetrahydropyridines using main group chemistry
dc.typeText
dcterms.embargo.expires2024-01-06
dcterms.embargo.terms2024-01-06
dcterms.rights.dplaThis 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.disciplineChemistry
thesis.degree.grantorColorado State University
thesis.degree.levelDoctoral
thesis.degree.nameDoctor of Philosophy (Ph.D.)

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