Skraup-Doebner-Von Miller quinoline synthesis revisited: reversal of the regiochemistry for gamma-aryl-beta,gamma-unsaturated alpha-ketoesters.
A reversal of the standard regiochemistry of the Skraup-Doebner-Von Miller quinoline synthesis was observed when anilines were condensed with gamma-aryl-beta,gamma-unsaturated alpha-ketoesters in refluxing TFA. The reaction is proposed to involve 1,2-addition of the anilines to gamma-aryl-beta,gamma-unsaturated alpha-ketoesters to form Schiff's base adducts, followed by cyclization and oxidation. The products were unambiguously shown to the 2-carboxy-4-arylquinolines by spectroscopy and X-ray crystallographic analysis.
Wu
Yan-Chao
YC
Center for Molecular Science, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, China.
Liu
Li
L
Li
Hui-Jing
HJ
Wang
Dong
D
Chen
Yong-Jun
YJ