tert-Butoxide-Mediated Synthesis of 3,4-Biquinolines from 2-Aminochalcones
- Authors
- Jeon, Jiye; Lee, So Young; Cheon, Cheol-Hong
- Issue Date
- 14-May-2019
- Publisher
- WILEY-V C H VERLAG GMBH
- Keywords
- Biquinolines; 2-Aminochalcones; Nucleophilic Catalyst; tert-Butoxide; Dimerization
- Citation
- ADVANCED SYNTHESIS & CATALYSIS, v.361, no.10, pp.2360 - 2364
- Indexed
- SCIE
SCOPUS
- Journal Title
- ADVANCED SYNTHESIS & CATALYSIS
- Volume
- 361
- Number
- 10
- Start Page
- 2360
- End Page
- 2364
- URI
- https://scholar.korea.ac.kr/handle/2021.sw.korea/65425
- DOI
- 10.1002/adsc.201900029
- ISSN
- 1615-4150
- Abstract
- A novel protocol to synthesize 3,4'-biquinolines from 2-aminochalcones in the presence of a stoichiometric amount of sodium tert-butoxide as the nucleophilic promotor was developed. Conjugate addition of tert-butoxide to 2-aminochalcones provided the corresponding enolates, which underwent Michael addition to another molecule of 2-aminochalcone to afford a dimeric species of 2-aminochalcones. Subsequent cyclization between the amino and carbonyl groups followed by aromatization provides 3,4'-biquinoline products. Various 2-aminochalcones were submitted to this protocol and the desired 3,4'-biquinoline products were obtained in good to high yields in a short reaction time.
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