3-Substituted Lawsones from Indanone Chalcones: Application of the House–Meinwald Rearrangement (HMR) for Chemoselective Ring Expansion

3-Substituted lawsones were synthesized via a chemoselective HMR-enabled ring expansion of indanone substrates. The transformation proceeds through epoxidation, quinone methide-type intermediate formation, ring expansion, and benzylic sp³ C-H oxidation. This operationally simple protocol provides direct access to 3-aryl- and 3-heteroaryl lawsones in moderate to good yields from readily available precursors capable of generating <i>ortho</i>/<i>para</i>-quinone methide-type intermediates. The method avoids transition-metal catalysis and prefunctionalization, offering a streamlined approach to highly functionalized 3-substituted lawsones.