A simple and highly efficient method for the preparation of tetrasubstituted NH-pyrrole from a wide range of chalcones and diethyl iminodiacetates via a Cu(OAc)2-promoted oxidation/[3+2]cycloaddition/aromatization cascade reaction has been developed. This reaction proceeds through dehydrogenations, deamination, and oxidative cyclization, affording the corresponding products in good to excellent yields. This convenient methodology for constructing tetrasubstituted NH-pyrroles has several advantages over existing methods, such as the use of easily accessible chalcones and readily available diethyl iminodiacetates, and mild reaction conditions. A wide range of substrates are tolerated.

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An efficient method for the synthesis of 2-substituted benzo[f]isoindole-4,9-dione derivatives from N-substituted iminodiacetates and quinones via a Cu(II)-promoted oxidation/[3+2] cycloaddition/aromatization tandem reaction was reported. This tandem reaction uses a wide range of N-substituted iminodiacetate derivatives which contain the chain-alkyl, cycloalkyl and aryl group on the N-atom. Based on optimized reaction conditions, the desired product of 2-substituted benzo[f]isoindole-4,9-diones were obtained in moderate to excellent yields. Taken together, the promising results of this research would provide an especially efficient strategy to synthesize polysubstituted pyrroles from easy available starting materials and promoted by cheaper Cu(OAc)2.

A novel one-pot 1,3-dipolar cycloaddition/oxidation reaction of 1,4-quinones, aromatic aldehydes, and N-substituted amino esters to construct polysubstituted benzo[ f]isoindole-4,9-diones induced by benzoic acid is reported. Based on optimized reaction conditions, various polysubstituted benzo[ f]isoindole-4,9-diones derivatives are obtained in moderate yields. This straightforward methodology employs mild reaction conditions, a green oxidant, and readily available starting materials. Notably, a wide range of substrates is tolerated.