Synthesis of 1-amino- and 1-hydroxy-9,10-anthraquinone derivatives based on reaction sequences between 2-acetyl-1,4-naphthoquinone and enamines

2-Acetyl-1,4-naphthoquinone was treated with pyrrolidine (or morpholine) enamines, derived from cyclic and acyclic ketones, in DMF at room temperature for 24–72 h to afford 3,4-disubstituted 1-pyrrolidino(or morpholino)-9,10-anthraquinones. On the other hand, when the treatment of 2-acetyl-1,4-naphthoquinone with enamines for 2 min was followed by addition of water and heating at 100°C for 2 h, the corresponding 1-hydroxy-9,10-naphthoquinone derivatives were obtained.