Synthesis of 2-Substituted Quinolines from 2-Aminostyryl Ketones Using Iodide as a Catalyst
- Authors
- Lee, So Young; Jeon, Jiye; Cheon, Cheol-Hong
- Issue Date
- 4-5월-2018
- Publisher
- AMER CHEMICAL SOC
- Citation
- JOURNAL OF ORGANIC CHEMISTRY, v.83, no.9, pp.5177 - 5186
- Indexed
- SCIE
SCOPUS
- Journal Title
- JOURNAL OF ORGANIC CHEMISTRY
- Volume
- 83
- Number
- 9
- Start Page
- 5177
- End Page
- 5186
- URI
- https://scholar.korea.ac.kr/handle/2021.sw.korea/75571
- DOI
- 10.1021/acs.joc.8b00552
- ISSN
- 0022-3263
- Abstract
- A new protocol for the synthesis of 2-substituted quinolines from 2-aminostyryl ketones has been developed using iodide as a nucleophilic catalyst. Conjugate addition of iodide to 2-aminostyryl ketones yielded the corresponding beta-iodoketones, which could have a conformation where the amino and carbonyl groups are proximal through free rotation about the C-alpha-C-beta single bond. Subsequent condensation between the amino and carbonyl groups followed by elimination of hydrogen iodide provided the corresponding quinolines, with regeneration of the iodide catalyst.
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