Treatment of 1,5-dibromo-2,4-dinitrobenzene (I) with pyrrolidine (II) afforded dipyrrolidino derivative (III). Reduction of the nitro groups of (III) by catalytic hydrogenation, followed by acetylation of amine (IV) provided diamide (V). Oxidative cyclization of (V) using H2O2 in the presence of formic acid gave rise to the dipyrroloimidazobenzimidazole system (VI). Quinone elaboration involved nitration of (VI) to (VII), nitro group reduction to amine (VIII), and finally amine oxidation employing Fremy's salt.