Ethyl-3-formyl-6-methoxy-(2 H)-chromene-2-carboxylate was transformed to N -substituted 1,2-dihydrochromeno[2,3-c]pyrrol-3-ones in a domino reductive amination-lactamization reaction. Isomerization of the double bond and the inherently labile stereogenic center was studied, and HPLC-ECD analysis of a chiral 1,2-dihydrochromeno[2,3-c]pyrrol-3(3a H)-one derivative aided by TDDFT-ECD calculation allowed configurational assignment of the separated enantiomers. Antiproliferative activity of the products was demonstrated on the CaCo-2 human epithelial colorectal adenocarcinoma cell line.
ASJC Scopus subject areas
- Organic Chemistry