Construction of 2-pyridones via oxidative cyclization of enamides: access to Pechmann dye derivatives

An efficient protocol for the construction of structurally diverse 2-pyridone derivatives from imines and α,β-unsaturated acid chlorides in a single operation is reported. The target compounds, including coumarin-8-oxoprotoberbine analogues and lamellarin G isomers, were prepared via thermal cyclization of the in situ generated enamides followed by thermal dehydrogenation. The cyclization of enamides was achieved by the introduction of an electron-withdrawing group on the α-carbon of acid chlorides. This methodology allows quick access to polycyclic Pechmann dyes via rare double oxidative cyclizations of dienamides under mild conditions.