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Synthesis of 2,3-dihydro-4(1H)-quinolones and the corresponding 4(1H)-quinolones via low-temperature fries rearrangement of N-arylazetidin-2-ones
journal contribution
posted on 2023-05-17, 19:07 authored by Lange, J, Alexander BissemberAlexander Bissember, Banwell, MG, Cade, IAN-Arylazetidin-2-ones of the general form 1, which are readily prepared by Goldberg–Buchwald-type copper-catalyzed coupling of N-unsubstituted azetidin-2-ones with the relevant aryl halide or using Mitsunobu cyclization processes, undergo smooth Fries-rearrangement in triflic acid at 0–18°C to give the isomeric 2,3-dihydro-4(1H)-quinolones (2). Dehydrogenation of the latter compounds using 10% Pd on C in 1.0 M aqueous sodium hydroxide/propan-2-ol mixtures at ca. 82°C provides the corresponding 4(1H)-quinolones (3).
History
Publication title
Australian Journal of ChemistryVolume
64Issue
4Pagination
454-470ISSN
0004-9425Department/School
School of Natural SciencesPublisher
CSIRO PublishingPlace of publication
150 Oxford St, Po Box 1139, Collingwood, Australia, Victoria, 3066Rights statement
Copyright 2011 CSIRORepository Status
- Restricted