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Methodology Development for the Electrophilic Aromatic Amination of Secondary Amides
dc.contributor.author | Fletcher, Randy | |
dc.date.accessioned | 2022-01-25 14:53:32 (GMT) | |
dc.date.available | 2024-01-26 05:50:05 (GMT) | |
dc.date.issued | 2022-01-25 | |
dc.date.submitted | 2022-01-19 | |
dc.identifier.uri | http://hdl.handle.net/10012/17959 | |
dc.description.abstract | The intramolecular electrophilic aromatic amination of secondary amides was developed. Secondary N-methoxy and N-p-methoxyphenyl amides were cyclized to oxindoles by triflic anhydride mediated electrophilic activation and subsequent oxidation with a pyridine N-oxide derivative. The electrophilic nitrogen species for the N-methoxy amide was isolated and characterized. Aryl tethered 2-amidopyridine- and 2-amidopyrimidine N-oxides were additionally discovered to be synthetically valuable sources of electrophilic nitrogen under mild conditions following a simple activation protocol of triflic anhydride and tertiary amine base. | en |
dc.language.iso | en | en |
dc.publisher | University of Waterloo | en |
dc.subject | organic synthesis | en |
dc.subject | methodology | en |
dc.subject | electrophilic amination | en |
dc.subject | secondary amides | en |
dc.subject | umpolung | en |
dc.title | Methodology Development for the Electrophilic Aromatic Amination of Secondary Amides | en |
dc.type | Master Thesis | en |
dc.pending | false | |
uws-etd.degree.department | Chemistry | en |
uws-etd.degree.discipline | Chemistry | en |
uws-etd.degree.grantor | University of Waterloo | en |
uws-etd.degree | Master of Science | en |
uws-etd.embargo.terms | 2 years | en |
uws.contributor.advisor | Fillion, Eric | |
uws.contributor.affiliation1 | Faculty of Science | en |
uws.published.city | Waterloo | en |
uws.published.country | Canada | en |
uws.published.province | Ontario | en |
uws.typeOfResource | Text | en |
uws.peerReviewStatus | Unreviewed | en |
uws.scholarLevel | Graduate | en |