Facile and concise procedures for the construction of indole fused N-heterocyclic systems were described. A series of benzo-, pyrido-, thieno-, naphtho-fused azepinoindolones and indolo-azepinoquinolinones has been prepared starting from indol-2-acetic acids. The required starting carboxylic acids 3a–e were readily obtained by the N-arylations of indoleacetic acid 1 with various aromatic halides 2a–e. Subsequent carboxylic acids were esterified, followed by the addition of Grignard reagents to afford the corresponding indole-based alcohols 5a–e. The key step in this protocol is the Friedel–Crafts cyclisations of these precursors promoted by AlCl₃/CH₃NO₂ or trifluoromethanesulfonic acid (TfOH) or polyphosphoric acid (PPA) catalysts to form the desired condensed indoles in moderate to good yields.