Two tandem catalytic systems are described for the synthesis of novel 3,4-disubstituted maleimides using the same Ugi adducts as starting materials. 4-Aryl-3-pyrrolyl- and 4-aryl-3-indolyl-maleimides were successfully obtained a Pd(OAc)/PPh based protocol. In contrast, maleimide-fused pyrrolo and indolo[1,2-]quinolines were obtained in a complementary methodology using CuI/L-proline. These strategies involved a combination of benzylic amine oxidation, -amidation, intramolecular Knoevenagel condensation, and -arylation reactions. Computational investigations provide further insights into this reaction sequence.
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