Synthesis 2007(24): 3891-3895  
DOI: 10.1055/s-2007-990869
PAPER
© Georg Thieme Verlag Stuttgart · New York

Chlorotrimethylsilane-Mediated Friedländer Synthesis of 2-(α-Chloroalkyl)quinoline Derivatives

Alexey S. Degtyarenkoa, Andrey A. Tolmachevb, Yulian M. Volovenkoa, Anton V. Tverdokhlebov*b
a Kiev National Taras Shevchenko University, Volodimirska Street 62, 01033 Kiev, Ukraine
b Enamine Ltd., Alexandra Matrosova Street 23, 01103 Kiev, Ukraine
Fax: +380(44)5373253; e-Mail: atver@univ.kiev.ua;
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Publikationsverlauf

Received 14 August 2007
Publikationsdatum:
31. Oktober 2007 (online)

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.