Alcohol Mediated Synthesis of 4‑Oxo-2-aryl‑4<i>H</i>‑chromene-3-carboxylate Derivatives from 4‑Hydroxycoumarins

Abstract

The unusual alcohol mediated formation of 4-oxo-2-aryl-4<i>H</i>-chromene-3-carboxylate (flavone-3-carboxylate) derivatives from 4-hydroxycoumarins and β-nitroalkenes in an alcoholic medium is described. The transformation occurs via the <i>in situ</i> formation of a Michael adduct, followed by the alkoxide ion mediated rearrangement of the intermediate. The effect of the different alcohol and nonalcohol media on the reaction was investigated