Synthesis of benzo[a]carbazoles via cyanide-catalyzed imino-Stetter reaction/Friedel-Crafts reaction sequence
- Authors
- Jeon, Jiye; Cheon, Cheol-Hong
- Issue Date
- 21-2월-2019
- Publisher
- ROYAL SOC CHEMISTRY
- Citation
- ORGANIC CHEMISTRY FRONTIERS, v.6, no.4, pp.456 - 467
- Indexed
- SCIE
SCOPUS
- Journal Title
- ORGANIC CHEMISTRY FRONTIERS
- Volume
- 6
- Number
- 4
- Start Page
- 456
- End Page
- 467
- URI
- https://scholar.korea.ac.kr/handle/2021.sw.korea/67600
- DOI
- 10.1039/c8qo01209a
- ISSN
- 2052-4110
- Abstract
- A new protocol to access benzo[a] carbazole derivatives was developed, via the cyanide-catalyzed iminoStetter reaction/ Friedel-Crafts reaction sequence. The cyanide-catalyzed imino-Stetter reaction of aldimines derived from 2-aminochalcones and aromatic aldehydes provided the corresponding 2-aryl-3-arenacylindole derivatives, which could be converted to benzo[a] carbazoles via intramolecular Friedel-Crafts ractions. Various 2-aminochalcones and aldehydes were applicable to this protocol, affording the desired benzo[a] carbazoles in good to high yields. Furthermore, we also developed a sequential protocol for the construction of benzo[a] carbazoles from 2-aminochalcones and aldehydes, without isolating any intermediates.
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