ChemInform Abstract: Electrophilic Aromatic Substitution with N-Methoxy-N-acylnitrenium Ions Generated from N-Chloro-N-methoxyamides: Syntheses of Nitrogen Heterocyclic Compounds Bearing a N-Methoxyamide Group.

ChemInform Abstract

The N-methoxyamides (III) and (VI) are prepared by coupling the carboxylic acids (I) and (V) with the O-methylhydroxylamine (II) via the corresponding acid chlorides. The amides undergo intramolecular ring closure of acylnitrenium ions intermediately generated by chlorination and subsequent dechlorination to give the indolones (IV). The compounds (VI) react with the arenes (VII) under analogous conditions, yielding the N-methoxyamides (VIII).