On the mechanism of the Skraup-Doebner-Von Miller quinoline synthesis.

@article{Denmark2006OnTM,
  title={On the mechanism of the Skraup-Doebner-Von Miller quinoline synthesis.},
  author={Scott E Denmark and Srikanth Venkatraman},
  journal={The Journal of organic chemistry},
  year={2006},
  volume={71 4},
  pages={1668-76}
}
The mechanism of the formation of substituted quinolines from anilines and alpha,beta-unsaturated ketones has been studied by the use of 13C-labeled ketones in cross-over experiments. In the reaction of doubly labeled 13C(2,4) mesityl oxide, a 100% scrambling of the label in the quinoline product was observed, whereas only a small (5-10%) amount of the starting mesityl oxide showed scrambling of the label. Similarly, the reaction of triply labeled pulegone clearly shows that the label in the… CONTINUE READING