Reversal of Reactivity\nof Heyns Intermediate for the\nConcise Synthesis of Substituted 3‑Hydroxyquinolines

An\nefficient and general method for the synthesis of\n3-hydroxyquinolines\nhas been achieved from <i>o</i>-acylanilines and α-hydroxyketones\nin good yields. The strategy involves the intramolecular reverse trapping\nof the <i>in situ</i> generated aminoenol intermediate with\nan electrophilic carbonyl, <i>viz</i>. an interrupted Heyns\nrearrangement, followed by aromatization. Important features include\ngood functional group tolerance, operational simplicity, gram-scale\nsynthesis, and broad synthetic utility.