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. (Figure presented.).
| Original language | English |
|---|---|
| Pages (from-to) | 2360-2364 |
| Number of pages | 5 |
| Journal | Advanced Synthesis and Catalysis |
| Volume | 361 |
| Issue number | 10 |
| DOIs | |
| Publication status | Published - 2019 May 14 |
Bibliographical note
Funding Information:This work was supported by National Research Foundation of Korea (NRF) grants funded by the Korean Government (NRF-2018R1D1A1A02086110, NRF-2017M2A8A4018045, and NRF-2014-011165, Center for New Directions in Organic Synthesis). J.J. acknowledges the financial support from an NRF-2018-Fostering Core Leaders of the Future Basic Science Program/Global Ph.D. Fellowship Program funded by the Korean Government.
Publisher Copyright:
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Keywords
- 2-Aminochalcones
- Biquinolines
- Dimerization
- Nucleophilic Catalyst
- tert-Butoxide
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry