Skip navigation
Skip navigation

Synthesis of 2,3-dihydro-4(1 H )-quinolones and the corresponding 4(1 H )-quinolones via low-temperature Fries rearrangement of N-arylazetidin-2-ones

Lange, Jens; Bissember, Alexander; Banwell, Martin; Cade, Ian


N-Arylazetidin-2-ones of the general form 1, which are readily prepared by GoldbergBuchwald-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 018°C to give the isomeric 2,3-dihydro-4(1H)-quinolones (2). Dehydrogenation of the latter compounds using 10% Pd on C in 1.0M aqueous sodium hydroxide/propan-2-ol mixtures at ca. 82°C provides the corresponding...[Show more]

CollectionsANU Research Publications
Date published: 2011
Type: Journal article
Source: Australian Journal of Chemistry
DOI: 10.1071/CH10465


File Description SizeFormat Image
01_Lange_Synthesis_of_2,3-dihydro-4(1_H_2011.pdf1.87 MBAdobe PDF    Request a copy

Items in Open Research are protected by copyright, with all rights reserved, unless otherwise indicated.

Updated:  19 May 2020/ Responsible Officer:  University Librarian/ Page Contact:  Library Systems & Web Coordinator