Chlorotrimethylsilane-mediated Friedländer synthesis of 2-(α-chloroalkyl) quinoline derivatives

…, AA Tolmachev, YM Volovenko, AV Tverdokhlebov

Index: Degtyarenko, Alexey S.; Tolmachev, Andrey A.; Volovenko, Yulian M.; Tverdokhlebov, Anton V. Synthesis, 2007 , # 24 p. 3891 - 3895

Full Text: HTML

Citation Number: 5

Abstract

Abstract Condensation of 2-aminoacetophenone and 2-aminobenzophenone with ethyl 4- chloro-3-oxobutanoate in the presence of excess chlorotrimethylsilane was shown to give ethyl 2-chloromethyl-3-quinoline carboxylates in high yields. A similar reaction with 1, 3- dichloroacetone and 2-chlorocyclohexanone led to the 3-chloro-2-(chloromethyl) quinolines and 4-chloro-1, 2, 3, 4-tetrahydroacridines, respectively.