The present work is based on the use of different synthetic methodologies using the pyrrole unit as a building block to construct new heterocyclic systems. A variety of fused and non-fused 7-azaindole derivatives were synthesized via ring opening of 3-substituted indoles and 3-nitrochromone, condensation with 4-chlorocoumarins, or using three multicomponent reactions. In addition, the azaindole backbone was subjected to typical coupling reactions.