Synthesis of fluorine-substituted anthraquinones and azaanthraquinones

Article abstract of DOI:10.1016/0022-1139(93)03030-P

Using 1,4-dipolar-aryne cycloaddition methodology, a convenient, short synthesis of several fluoroanthraquinones is presented which involves the reaction of haloarenes and 3-cyanophthalides in the presence of lithium diisopropylamide (LDA) in tetrahydrofuran (THF).The fluorine substituent(s) can be introduced by using fluorine-substituted haloarenes and/or 3-cyanophthalides.Similarly, fluorine-substituted pyridines can be prepared by treating fluorine-substituted cyanophthalides and halopyridines in the presence of lithium diisopropylamide.