A practical and efficient regioselective synthesis of pyrrolo-fused polyheterocycliccompounds from 2-substituted-2-hydroxy-indane-1,3-diones and 1,4-benzoxazinones via intramolecular [3+2] cycloaddition has been demonstrated. The protocol obviates column chromatography and products were isolated in good to excellent yields by simple filtration. Electronic effects of both electron-releasing and electron-withdrawing