Abstract
Acid catalyzed Friedlander reactions of a number of 2,3-dihydro-1H- cyclopenta[b]quinoxaline-1-ones with 2-aminobenzaldehyde yield, unexpectedly, 8H-indolo[3,2-a]phenazine and quinolino[2,3-c]cyclopentadienone[2,3-b] quinoxalines, the structures of derivatives of which were confirmed by X-ray crystallography. Easy routes to novel quinoxaline-based indoles, quinolones, and quinoxaline-1,4-dioxides are reported, and proposed mechanisms for the unexpected products are discussed.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 3704-3707 |
| Number of pages | 4 |
| Journal | Organic Letters |
| Volume | 14 |
| Issue number | 14 |
| DOIs | |
| State | Published - Jul 20 2012 |
ASJC Scopus subject areas
- Organic Chemistry
- Physical and Theoretical Chemistry
- Biochemistry
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Shoker, T. A., Ghattass, K. I., Fettinger, J. C., Kurth, M. J., & Haddadin, M. J. (2012). Unusual friedlander reactions: A route to novel quinoxaline-based heterocycles. Organic Letters, 14(14), 3704-3707. https://doi.org/10.1021/ol301550e