Abstract
The Doebner-Miller synthesis of quinolines under modified biphasic conditions was investigated. Crotonaldehyde, reacted readily with aniline to produce 2-methylquinoline. However, cinnamaldehyde and other γ-substituted α,β-unsaturated aldehydes yielded complex mixtures with substituted anilines to provide only trace quantities of quinolines. The Doebner-Miller reaction under these conditions is only suitable for sterically accessible α,β-unsaturated aldehydes.
| Original language | English |
|---|---|
| Article number | P11410SS |
| Pages (from-to) | 3645-3648 |
| Number of pages | 4 |
| Journal | Synthesis |
| Volume | 2010 |
| Issue number | 21 |
| DOIs | |
| Publication status | Published - Nov 2010 |
| Externally published | Yes |
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Reynolds, K. A., Young, D. J., & Loughlin, W. A. (2010). Limitations of the two-phase doebner-miller reaction for the synthesis of quinolines. Synthesis, 2010(21), 3645-3648. [P11410SS]. https://doi.org/10.1055/s-0030-1258258