Synthesis of 2,5-Dibutyl-3,6-dimethyl-1H,2H,4H,5H-pyrrolo[3,4-c]pyrrole-1,4-dione: A Diketopyrrolopyrrole Scaffold for the Formation of Alkenyldiketopyrrolopyrrole Compounds

This manuscript describes an unprecedented and efficient synthesis of a new DPP scaffold, 2,5-dibutyl-3,6-dimethyl-1H,2H,4H,5H-pyrrolo[3,4-c]pyrrole-1,4-dione (DMDPP), containing methyl groups at the 3,6-positions as a precursor to preparing 3,6-divinyl-substituted DPP compounds. Subsequently, following the synthesis of DMDPP, we performed an efficient and mild C–H functionalization of the methyl groups with a variety of aromatic aldehydes to synthesize the first examples of 3,6-divinyl-substituted DPP compounds in moderate to good yields.