3-Substituted Lawsones from Indanone Chalcones: Application of the House-Meinwald Rearrangement (HMR) for
Mohan Banyangala1,2, Jayamurthy Purushothaman2,3, Sasidhar B Somappa1,2
1Chemical Sciences and Technology Division, Council of Scientific and Industrial Research (CSIR)-National Institute for Interdisciplinary Science and Technology (NIIST), Thiruvananthapuram-695019, India.
Abstract:
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 ortho/para-quinone methide-type intermediates. The method avoids transition-metal catalysis and prefunctionalization, offering a streamlined approach to highly functionalized 3-substituted lawsones.
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