The Oxidation of the 2-Methyl Group of 3-Substituted 2-Methylindoles by Autoxidation and with Silver Acetate in Carboxylic Acids

Article abstract of DOI:10.1246/bcsj.55.3861

The autoxidation of 3-alkyl-2-methylindoles in carboxylic acids, such as propionic acid and acetic acid, at the reflux temperature resulted in the selective oxidation of the 2-methyl group and the formation of 3-alkyl-2-formylindoles. The formation of the 2-formylindoles was dependent on the nature of the solvent used. The treatment of 3-benzoyl-1,2-dimethylindole with silver acetate gave 2-acetoxymethyl-3-benzoyl-1-methylindole and 3-benzoyl-2-formyl-1-methylindole. The mechanistic implications for the autoxidation and the oxidation with silver acetate are presented.