1,2-Dihydrochromeno[2,3-c]pyrrol-3-one Derivatives: Synthesis and HPLC-ECD Analysis

Published as part of the Special Section 10th EuCheMS Organic Division Young Investigator Workshop

Abstract

Ethyl-3-formyl-6-methoxy-(2H)-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(3aH)-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.

Key words

1,2-dihydrochromeno[2,3-c]pyrrol-3-one - isomerization - HPLC-ECD - TDDFT-ECD - antiproliferative

• References and Notes

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