title: Skraup-Doebner-Von Miller quinoline synthesis revisited: reversal of the regiochemistry for gamma-aryl-beta,gamma-unsaturated alpha-ketoesters.
abstract: 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.
authors.affiliation: Center for Molecular Science, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, China.
authors.forename: Yan-Chao
authors.initials: YC
authors.lastname: Wu
authors.forename: Li
authors.initials: L
authors.lastname: Liu
authors.forename: Hui-Jing
authors.initials: HJ
authors.lastname: Li
authors.forename: Dong
authors.initials: D
authors.lastname: Wang
authors.forename: Yong-Jun
authors.initials: YJ
authors.lastname: Chen