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.
A series of more than 20 multisubstituted pyrrolidine-2-carboxylates were synthesized via a one-pot cycloaddition of an araldehyde, an amino acid ester, and a chalcone catalyzed by I2/K2CO3 in tetrahydrofuran at 80 °C. The advantages of this method are readily available starting materials, mild conditions, and simple operation, and it is metal free and yields are good to excellent.
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.
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