Introduction of 2, 4-pentadienyl side chain to halogenated p-quinones is performed with (2, 4- pentadienyl) trimethylstannane to afford 2-halo-3-(2, 4-pentadienyl)-1, 4-quinones. Pyrolytic decomposition of the corresponding azidoquinones derived from the obtained haloquinones affords 3H-pyrrolo [1, 2-a] indol-5, 8-dione derivatives in good yields.