A variety of functionalized N-alkoxyindole-3-carbonitrilederivatives are achieved under remarkably mild conditionsby applying a FeCl3-mediated intramolecular heterocyclization of 3-alkoxyimino-2-arylalkylnitriles. This novel synthesisallows the N-moiety on the side chain to be annulated to thebenzene ring as the final synthetic step, which enables thefunctionalization of the benzenoid portion of the indole atan early stage of the synthesis.