Various diarylpyrrole-2-carbaldehydes were prepared in good to excellent yields by a ring transformation of arylfurfuran-2-carbaldehydes with anilines in the presence of an acid catalyst. All the synthesized compounds were duly characterized through their elemental analyses and by spectroscopic techniques (FTIR, 1HNMR, 13CMR, and mass). These were screened for their antibacterial and antioxidant activities.