Abstract
Synthesis of the strained 2H-thieto[3,2-b]quinoline ring system is reported for the first time. Treatment of (Z)-2-benzyliden-2H-thieto[3,2-b]quinoline derivatives of this heterocycle with base, at reflux in ethanol, causes a novel rearrangement to 2-phenylthieno[3,2-b]quinolines. Indeed, the one-pot reaction of 2-aminobenzaldehydes and (Z)-2-benzylidenethietan-3-one in refluxing basic ethanol leads directly to 2-phenylthieno[3,2-b]quinolines in good yields.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 6687-6689 |
| Number of pages | 3 |
| Journal | Tetrahedron Letters |
| Volume | 51 |
| Issue number | 51 |
| DOIs | |
| State | Published - Dec 22 2010 |
Keywords
- Base-mediated rearrangement
- Friedländer reaction
- Thieno[3,2-b]quinoline
- Thieto[3,2-b]quinoline
ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry
- Drug Discovery
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Cite this
Haddadin, M. J., El-Nachef, C., Kisserwani, H., Chaaban, Y., Kurth, M. J., & Fettinger, J. C. (2010). 2-Benzyliden-2H-thieto[3,2-b]quinoline: A new heterocycle and its rearrangement to 2-phenylthieno[3,2-b]quinoline. Tetrahedron Letters, 51(51), 6687-6689. https://doi.org/10.1016/j.tetlet.2010.10.039