Limitations of the 'Two-Phase' Doebner-Miller Reaction for the Synthesis of Quinolines

[摘要]：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 gamma-substituted alpha,beta-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 alpha,beta-unsaturated aldehydes.

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