A synthetic novel strategy involving a pseudo three component reaction to obtain 1,6-dihydroazaazulenes derivates via cyclization of pyrrolyl-enones by a novel pseudo three-component reaction was developed. This reaction is carried out under mild conditions from simple starting materials and catalyzed with ionic liquid. Notably, 3 new C-C bonds are formed in the one-pot process. The target molecules are of interest in medicinal chemistry as they contain a privileged scaffold and are considered indole homologues.