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 |
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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 |