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Functionalization of pyridines and pyrimidines via ring-opened intermediates

dc.contributor.authorUhlenbruck, Benjamin J. H., author
dc.contributor.authorMcNally, Andrew, advisor
dc.contributor.authorMiyake, Garret, committee member
dc.contributor.authorChung, Jean, committee member
dc.contributor.authorKipper, Matt, committee member
dc.date.accessioned2025-09-01T10:44:01Z
dc.date.available2026-08-25
dc.date.issued2025
dc.description.abstractPyridines and pyrimidines are prevalent in pharmaceuticals and agrochemicals, yet site-selective functionalization methods of these valuable structures are often limited. In this dissertation, we describe the development of pyridine and pyrimidine functionalization methods that will enable organic chemists to access functionalized heterocyclic materials more easily. Chapter One describes the importance of pyridines and pyrimidines in industry, along with current methods and limitations in functionalizing these azines. Chapter Two introduces a 3-selective chlorination of pyridines using ring-opened Zincke imine intermediates. The method differs from a method our group reported in 2022 by ring-opening pyridine with aniline instead of dibenzylamine. Ring-opening azines with aniline produces imines and N-Ph azine salts with interesting properties, and enables the transformations described in every chapter of this dissertation. Chapter Three describes a 3-selective fluorination of pyridines using Zincke imine intermediates. Chapter Four provides an overview of Structure-Activity-Relationship (SAR) studies, de novo heterocycle synthesis, and skeletal editing strategies, then describes a deconstruction-reconstruction approach for pyrimidine diversification. Chapter Five discusses stable isotopes in medicinal chemistry, then expands on the deconstruction-reconstruction strategy for stable isotope incorporation into pyrimidines.
dc.format.mediumborn digital
dc.format.mediumdoctoral dissertations
dc.identifierUhlenbruck_colostate_0053A_19108.pdf
dc.identifier.urihttps://hdl.handle.net/10217/241895
dc.identifier.urihttps://doi.org/10.25675/3.02215
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.rights.accessEmbargo expires: 08/25/2026.
dc.subjectheterocycle
dc.subjectorganic chemistry
dc.subjectC-H functionalization
dc.subjectskeletal editing
dc.subjectlate-stage functionalization
dc.titleFunctionalization of pyridines and pyrimidines via ring-opened intermediates
dc.typeText
dcterms.embargo.expires2026-08-25
dcterms.embargo.terms2026-08-25
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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