Synthesis and Mechanistic Insights of the Formation of 3-Hydroxyquinolin-2-ones including Viridicatin from 2-Chloro-,3-diaryloxirane-2-carboxamides under Acid-Catalyzed Rearrangements.

-Benzyl-2-chloro-,3-diaryloxirane-2-carboxamides, easily obtained from aromatic aldehydes and anilides of dichloroacetic acid under Darzens condensation conditions, proved to be excellent starting compounds for the synthesis of 3-hydroxyindolin-2-ones, cyclohepto[]pyrrole-2,3-diones, and 1-azaspiro[4.5]deca-3,6,9-triene-2-ones via the C(sp)-C(sp) bond formation in the first case and C(sp)-C(sp) bond formation in the second and third cases. Under optimized reaction conditions, 3-hydroxyindolin-2-ones are obtained in a one-pot process, which involves the treatment of -benzyl-2-chloro-,3-diaryloxirane-2-carboxamides with CFCOH or AcOH/HSO.

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.

pH-controlled photoinduced electron transfer in the [(Mo6Cl8)L6]-calix[4]resorcine-dimethylviologen system.

A pH-controlled photoinduced electron transfer in the supramolecular system [(Mo(6)Cl(8))L(6)]-calix[4]resorcine-dimethylviologen is reported.