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

J Lange, AC Bissember, MG Banwell, IA Cade

Index: Lange, Jens; Bissember, Alex C.; Banwell, Martin G.; Cade, Ian A. Australian Journal of Chemistry, 2011 , vol. 64, # 4 p. 454 - 470

Full Text: HTML

Citation Number: 10

Abstract

Abstract N-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 ...