Structural assignment of the enol-keto tautomers of one-pot synthesized 4-hydroxyquinolines/4-quinolones
- Authors
- Kang, OY[Kang, On-Yu]; Park, SJ[Park, Seong Jun]; Ahn, H[Ahn, Hyojung]; Jeong, KC[Jeong, Kyung Chae]; Lim, HJ[Lim, Hwan Jung]
- Issue Date
- 21-Jan-2019
- Publisher
- ROYAL SOC CHEMISTRY
- Citation
- ORGANIC CHEMISTRY FRONTIERS, v.6, no.2, pp.183 - 189
- Indexed
- SCIE
SCOPUS
- Journal Title
- ORGANIC CHEMISTRY FRONTIERS
- Volume
- 6
- Number
- 2
- Start Page
- 183
- End Page
- 189
- URI
- https://scholarworks.bwise.kr/skku/handle/2021.sw.skku/11298
- DOI
- 10.1039/c8qo00884a
- ISSN
- 2052-4129
- Abstract
- The one-pot preparation of 2,3-disubstituted 4-quinolones and the structural assignment of their tautomers are described. The mono-selective Michael addition of anilines to alpha,alpha-dioxoketene dithioacetals followed by thermal cyclization of the crude N, S-acetals gave the desired 4-hydroxyquinolines in good to excellent yields. The tautomeric structures of the obtained products were confirmed by X-ray crystallography, IR, and NMR experiments. Spectroscopic data revealed that the equilibrium between the enol and keto forms of the bicyclic system was determined by the strength of the internal H-bonds. A H-bond acceptor at the 3-position favored the enol form via 6-membered intramolecular H-bonding. A H-bond acceptor at the 2- or 8-position completely switched the equilibrium to favor the keto form possibly due to extended conjugation and H-bonding. The experimental assignments were perfectly matched with the results of DFT calculation.
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