Synthesis of N-Substituted Aryl Amidines by Strong Base Activation of Amines

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dc.contributor.authorKhalifa, Muhammad
dc.date.accessioned2015-08-13T18:56:58Z
dc.date.available2015-08-13T18:56:58Z
dc.date.issued2014-09
dc.description52 pages. A thesis presented to the Department of Chemistry, Biochemistry, and the Clark Honors College of the University of Oregon in partial fulfillment of the requirements for degree of Bachelor of Science, Fall 2014.en_US
dc.description.abstractThis project describes an efficient method for the direct preparation of N-substituted aryl amidines from nitriles and primary amines. The method employs activation of amines by a strong base and provides greater access to a pharmaceutically relevant functional group. The creation of functionalized amidines and salient amidine-containing moieties via the newly described route was explored. This synthetic approach tolerates deactivated nitriles, nitriles with competing nucleophilic aromatic substitution sites, and aryl amines. Serial amidine formation is also possible, leading to new routes for the creation of tetrahydropyrimidines, benzimidazoles, and bis-amidines. The method described herein features superior yields, improved material and time economy, and greater starting material compatibility compared to other established routes of amidine synthesis. Additionally, this project led to the creation and characterization of six compounds hitherto undescribed in the literature.en_US
dc.identifier.urihttps://hdl.handle.net/1794/19139
dc.language.isoen_USen_US
dc.publisherUniversity of Oregonen_US
dc.rightsCreative Commons BY-NC-ND 4.0-USen_US
dc.subjectOrganic chemistryen_US
dc.subjectBiochemistryen_US
dc.subjectSynthesisen_US
dc.subjectPharmaceutical chemistryen_US
dc.subjectAmidinesen_US
dc.subjectMethodsen_US
dc.subjectAminesen_US
dc.subjectNitrilesen_US
dc.titleSynthesis of N-Substituted Aryl Amidines by Strong Base Activation of Aminesen_US
dc.typeThesis / Dissertationen_US

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