Synthesis of 3‑Hydroxy-4-arylquinolin-2-ones Including Viridicatol via a Darzens Condensation/Friedel–Crafts Alkylation Strategy

The
new efficient synthesis of biologically important 3-hydroxy-4-arylquinolin-2-ones
through the Darzens condensation (epoxidation) of dichloroacetanilides
with aromatic aldehydes followed by one-pot dechlorative epoxide-arene
cyclization is described. This methodology has been utilized for the
synthesis of naturally occurring viridicatol, a fungal metabolite
isolated from the penicillium species.