Synthesis of 4-perfluoroalkylquinolines

Abstract

4-(C n−1F 2n−1)-Substituted quinolines (n = 2–4) are obtained by the reaction of 2-(C nF 2n+1)-substituted anilines 1 with lithium enolate of acetaldehyde. A similar treatment of 1 with lithium enolates of methyl ketones, the treatment of 1 with lithium phenylacetylide or cyclization of ketimines derived from 1 and aryl methyl ketones furnish the corresponding 2-aryl-4-perfluoroalkylquinolines. The reaction of 1 with lithiated carbonitriles RCH(Li)CN (R = H, alkyl) provides an easy access to 2-amino-4-perfluoroalkyl-3-R-quinolines.