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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
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 |
| UTAS Author: | Bissember, AC (Associate Professor Alex Bissember) |
| ID Code: | 85980 |
| Year Published: | 2011 |
| Web of Science® Times Cited: | 16 |
| Deposited By: | Chemistry |
| Deposited On: | 2013-08-19 |
| Last Modified: | 2017-10-25 |
| Downloads: | 0 |
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