Methodology Development for the Electrophilic Aromatic Amination of Secondary Amides
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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.
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Randy Fletcher (2022). Methodology Development for the Electrophilic Aromatic Amination of Secondary Amides. UWSpace. http://hdl.handle.net/10012/17959