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 o-acylanilines and α-hydroxyketones in good yields. The strategy involves the intramolecular reverse trapping of the in situ generated aminoenol intermediate with an electrophilic carbonyl, viz. an interrupted Heyns rearrangement, followed by aromatization. Important features include good functional group tolerance, operational simplicity, gram-scale synthesis, and broad synthetic utility.