An efficient microwave synthesis of 1- {3-or 4-[bis(1H-indol-3-yl)methyl]benzyl}-2-{3-or 4-[bis(1H-indol-3yl)methyl]phenyl}-1H-benzimidazole derivatives was achieved. This novel azaheterocyclic hybrid scaffold was assembled in excellent overall yield through two-consecutive ABB-type 3CR design by the reaction of (3-or 4formylphenyl)diindolylmethanes, synthesized from a mixture of isophthalaldehyde or terephthalaldehyde, respectively, 1H-indole or derivatives, and ortho-phenylenediamine. The use of microwave technology, catalyst-free, and solvent-free conditions, as well as the avoidance of time-consuming and tedious workup procedure, make it an appealing method to access a novel (1DIMB-2DIMP)BZ scaffold endowed with potential biological activity.