Tandem four-component reaction for efficient synthesis of dihydrothiophene with substituted amino acid ethyl esters

Abstract

The one-pot four-component reaction of aromatic aldehydes, malononitrile, 1,3-thiazolidinedione and ethyl glycinate hydrochloride in ethanol in the presence of triethylamine afforded trans-dihydrothiophene ureidoformamide derivatives in moderate to good yields. The other α-amino acid ethyl esters resulted in the corresponding diastereoisomeric dihydrothiophene derivatives with various molecular ratios. The functionalized thiophene derivatives were also successfully prepared by sequential dehydrogenation reaction with DDQ.