A Regiospecific Synthesis of 2‐Azaanthraquinon‐3‐ones via a Hetero‐ Diels‐Alder Reaction with Bromonaphthoquinones.

Abstract The Diels-Alder reaction 2-azadienes and 2- or 3-bromo-5-substituted naphthoquinones (R 3 =OH, OAc, OMe) led to a regiospecific synthesis of the corresponding 2-azaanthraquinones-3-ones. The results indicate that the bromine atom exerts a stronger regiochemical control in these cycloaddition than the 5-substituent.