2, 3-Dichloro-N-phenylmaleimide 2 undergoes nucleophilic substitution reactions by a variety of nucleophiles giving either monosubstituted 5 or disubstituted 3 products. Treatment of 5 with sodium azide at room temperature results in cyclization to the corresponding 2-phenylpyrrolo [3, 4-b] quinoxaline-1, 3-diones 6, while at higher temperatures 5 is reduced to the 2-amino-3-amino-N-phenylmaleimides7.