Structural assignment of the enol-keto tautomers of one-pot synthesized 4-hydroxyquinolines/4-quinolones
DC Field | Value | Language |
---|---|---|
dc.contributor.author | Kang, OY[Kang, On-Yu] | - |
dc.contributor.author | Park, SJ[Park, Seong Jun] | - |
dc.contributor.author | Ahn, H[Ahn, Hyojung] | - |
dc.contributor.author | Jeong, KC[Jeong, Kyung Chae] | - |
dc.contributor.author | Lim, HJ[Lim, Hwan Jung] | - |
dc.date.accessioned | 2021-07-28T21:25:42Z | - |
dc.date.available | 2021-07-28T21:25:42Z | - |
dc.date.created | 2019-11-28 | - |
dc.date.issued | 2019-01-21 | - |
dc.identifier.issn | 2052-4129 | - |
dc.identifier.uri | https://scholarworks.bwise.kr/skku/handle/2021.sw.skku/11298 | - |
dc.description.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. | - |
dc.publisher | ROYAL SOC CHEMISTRY | - |
dc.subject | PYRIDONECARBOXYLIC ACIDS | - |
dc.subject | X-RAY | - |
dc.subject | QUINOLONE | - |
dc.subject | 2-ARYL-4-QUINOLONES | - |
dc.subject | DERIVATIVES | - |
dc.subject | IVACAFTOR | - |
dc.subject | DISCOVERY | - |
dc.subject | VERSATILE | - |
dc.subject | CX-5461 | - |
dc.subject | VX-770 | - |
dc.title | Structural assignment of the enol-keto tautomers of one-pot synthesized 4-hydroxyquinolines/4-quinolones | - |
dc.type | Article | - |
dc.contributor.affiliatedAuthor | Kang, OY[Kang, On-Yu] | - |
dc.identifier.doi | 10.1039/c8qo00884a | - |
dc.identifier.scopusid | 2-s2.0-85060005767 | - |
dc.identifier.wosid | 000457264600004 | - |
dc.identifier.bibliographicCitation | ORGANIC CHEMISTRY FRONTIERS, v.6, no.2, pp.183 - 189 | - |
dc.relation.isPartOf | ORGANIC CHEMISTRY FRONTIERS | - |
dc.citation.title | ORGANIC CHEMISTRY FRONTIERS | - |
dc.citation.volume | 6 | - |
dc.citation.number | 2 | - |
dc.citation.startPage | 183 | - |
dc.citation.endPage | 189 | - |
dc.type.rims | ART | - |
dc.type.docType | Article | - |
dc.description.journalClass | 1 | - |
dc.description.journalRegisteredClass | scie | - |
dc.description.journalRegisteredClass | scopus | - |
dc.relation.journalResearchArea | Chemistry | - |
dc.relation.journalWebOfScienceCategory | Chemistry, Organic | - |
dc.subject.keywordPlus | PYRIDONECARBOXYLIC ACIDS | - |
dc.subject.keywordPlus | X-RAY | - |
dc.subject.keywordPlus | QUINOLONE | - |
dc.subject.keywordPlus | 2-ARYL-4-QUINOLONES | - |
dc.subject.keywordPlus | DERIVATIVES | - |
dc.subject.keywordPlus | IVACAFTOR | - |
dc.subject.keywordPlus | DISCOVERY | - |
dc.subject.keywordPlus | VERSATILE | - |
dc.subject.keywordPlus | CX-5461 | - |
dc.subject.keywordPlus | VX-770 | - |
Items in ScholarWorks are protected by copyright, with all rights reserved, unless otherwise indicated.
(03063) 25-2, SUNGKYUNKWAN-RO, JONGNO-GU, SEOUL, KOREAsamsunglib@skku.edu
COPYRIGHT © 2021 SUNGKYUNKWAN UNIVERSITY ALL RIGHTS RESERVED.
Certain data included herein are derived from the © Web of Science of Clarivate Analytics. All rights reserved.
You may not copy or re-distribute this material in whole or in part without the prior written consent of Clarivate Analytics.