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Methodology Development for the Electrophilic Aromatic Amination of Secondary Amides

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Fletcher_Randy.pdf (1.77 MB)

Date

2022-01-25

Authors

Fletcher, Randy

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Publisher

University of Waterloo

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.

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Keywords

organic synthesis, methodology, electrophilic amination, secondary amides, umpolung

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URI

http://hdl.handle.net/10012/17959

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Chemistry