eCite Digital Repository

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

Citation

Lange, J and Bissember, AC and Banwell, MG and Cade, IA, Synthesis of 2,3-dihydro-4(1H)-quinolones and the corresponding 4(1H)-quinolones via low-temperature fries rearrangement of N-arylazetidin-2-ones, Australian Journal of Chemistry, 64, (4) pp. 454-470. ISSN 0004-9425 (2011) [Refereed Article]

Copyright Statement

Copyright 2011 CSIRO

DOI: doi:10.1071/CH10465

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 sodium hydroxide/propan-2-ol mixtures at ca. 82°C provides the corresponding 4(1H)-quinolones (3).

Item Details

Item Type:Refereed Article
Research Division:Chemical Sciences
Research Group:Organic Chemistry
Research Field:Organic Chemical Synthesis
Objective Division:Expanding Knowledge
Objective Group:Expanding Knowledge
Objective Field:Expanding Knowledge in the Chemical Sciences
Author:Bissember, AC (Dr Alex Bissember)
ID Code:85980
Year Published:2011
Web of Science® Times Cited:11
Deposited By:Chemistry
Deposited On:2013-08-19
Last Modified:2017-10-25
Downloads:0

Repository Staff Only: item control page