ELECTROPHILIC SUBSTITUTION REACTIONS OF ALKYLATED 2-AMINOINDOLE DERIVATIVES

Article abstract of DOI:10.1007/BF00519148

Bromination, nitration, and acylation of 1-methyl-2-dimethylaminoindole under mild conditions proceed to give the 3-substituted reaction products.In acidic media, in which the parent indole exists in the form of an amidinium cation, substitution occurs in the 5-position of the benzene ring.Aminoindoles, which are capable of existing only in the iminoindoline or aminoindolenine forms, always give products derived from substitution at the para position relative to the nitrogen atom, regardless of the reaction conditions.