A novel method of indole ring system construction: One-pot synthesis of 4-and 6-nitroindole derivatives via base promoted reaction between 3-nitroaniline and …
ABSTRACT: Base promoted condensation of ketones RCOCH2R′ with 3-nitroaniline results in formation of the corresponding 4-and 6-nitro-2-R-3-R′-indoles. This multistep process apparently includes oxidative nucleophilic substitution of hydrogen in the aromatic ring of the aniline by the anotale anion and subsequent cyclization of the so formed ortho- aminoketone intermediate to indoles via a Baeyer type reaction.
