2,6-Diamino-4,8-dioxo-1,4,5,8-tetrahydropyrrolo[2,3-f]indole-3,7-dicarbonitrile derivatives (5a-g) were prepared by treatment of chloranil with two equivalents of malononitrile in presence of a basic catalyst given dimalononitrile derivative 3, and the latter reacts with two equivalents of a series of primary aromatic or aliphatic amines bearing different substituents in the para position. The resulting compounds were characterized by elemental and spectral analyses. In addition, the biological screening of selected samples was tested.