A convergent synthesis of indolylpyrrole derivatives has been developed from domino coupling of α-azido ketones, aromatic aldehydes, and 3-cyanocetylindoles in the presence of piperidine in aqueous medium at 80 °C via cascade Knoevenagel condensation–Michael addition–annulation in excellent yields. Further, the synthesized <i>ortho</i>-azidoindolylpyrroles undergo [3+2] cycloaddition with phenyl acetylene to give indolyltriazolylpyrrole hybrids in good yields. This domino transformation, efficiently generates C–C and C–N bonds in a minimum of synthetic steps resulting in three important bioactive heterocyclic frameworks, indole–pyrrole–triazole hybrids.