Abstract
An efficient procedure for the synthesis of the azocinoACHTUNGTRENUNG[5,4- b]indole framework is presented, relying on a cationic gold-catalyzed intramolecular alkyne hydroarylation of propargylic amides derived from various tryptamines and 3-substituted 2- propynoic acids. The triphenylphosphinegold(I) chloride/silver(I) triflate catalytic system was found to be superior to our previously described mercury( II) triflate catalyst, and hence the substrate scope of the process was significantly expanded.
| Original language | English |
|---|---|
| Pages (from-to) | 2841-2848 |
| Number of pages | 8 |
| Journal | Advanced Synthesis and Catalysis |
| Volume | 354 |
| Issue number | 14-15 |
| DOIs | |
| Publication status | Published - Oct 8 2012 |
| Externally published | Yes |
Keywords
- C-C coupling
- Cyclization
- Gold catalysis
- Medium-ring compounds
- Nitrogen heterocycles
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry
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Cite this
Peshkov, V. A., Pereshivko, O. P., & Der Eycken, E. V. V. (2012). Synthesis of azocino[5,4-b]indoles via gold-catalyzed intramolecular alkyne hydroarylation. Advanced Synthesis and Catalysis, 354(14-15), 2841-2848. https://doi.org/10.1002/adsc.201200305