An efficient Pd-catalyzed selective intramolecular arylation of functionalized N,N′-substituted 1-aminoindoles has been reported. In all cases, the reactions take place rapidly in DMA and efficiently proceed in the presence of a Pd(OAc)2/Dpephos catalytic system, furnishing the fused indolo[2,1-a]phthalazines in high yields. Additionally, the one-pot double C–H arylation at positions C-2 and C-3 of N,N′-substituted 1-aminoindoles is effective and leads to unknown complex scaffolds of biological interest.