Reversal of Reactivity of Heyns Intermediate for the Concise Synthesis of Substituted 3-Hydroxyquinolines.

An efficient and general method for the synthesis of 3-hydroxyquinolines has been achieved from -acylanilines and α-hydroxyketones in good yields. The strategy involves the intramolecular reverse trapping of the generated aminoenol intermediate with an electrophilic carbonyl, . an interrupted Heyns rearrangement, followed by aromatization. Important features include good functional group tolerance, operational simplicity, gram-scale synthesis, and broad synthetic utility.