SYNTHESIS OF 4-PERFLUOROALKYLQUINOLINES

4-(Cn-1F2n-1)-Substituted quinolines (n = 2-4) are obtained by the rea ction of 2-(CnF2n+1)-substituted anilines 1 with lithium enolate of ac etaldehyde. A similar treatment of 1 with lithium enolates of methyl k etones, the treatment of 1 with lithium phenylacetylide or cyclization of ketimines derived from 1 and aryl methyl ketones furnish the corre sponding 2-aryl-4-perfluoroalkylquinolines. The reaction of 1 with lit hiated carbonitriles RCH(Li)CN (R = H, alkyl) provides an easy access to 2-amino-4-perfluoroalkyl-3-R-quinolines. (C) 1998 Elsevier Science Ltd. All rights reserved.