Manganese(III) Acetate Initiated Oxidative Free Radical Reaction between 2-Anilino-1,4-naphthoquinones and Diethyl Malonate

A free radical reaction between 2-anilino-1,4-naphthoquinones and diethyl malonate initiated by manganese (III) acetate is described. This reaction provides a novel method for the synthesis of 5,6,11,12-tetra-hydro-6,11-dioxo-benzo[b]acridines. With a meta substituent on the anilino group, this reaction shows poor to high regioselectivity depending on the steric effect of the substituents on the anilino group and malonate.