Synthesis of 1-Substituted 3H-Naphtho[1,2,3-de]quinoline-2,7-diones

A method for preparing 1-tosyl-3 H -naphtho[1,2,3- de ]quinoline-2,7-diones by the reaction of N -(9,10-anthraquinon-1-yl)chloroacetamide with sodium p -toluenesulfinate has been developed. Nucleophilic substitution of the tosyl group by nitrogen and oxygen nucleophiles has been found to proceed under mild conditions. The corresponding 1-substituted 3 H -naphtho[1,2,3- de ]quinoline-2,7-diones have been obtained by the reaction of these compounds with amines, phenol, sodium hydroxide, and sodium azide.