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