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

Alexey S. Degtyarenko; Andrey A. Tolmachev; Yulian M. Volovenko; Anton V. Tverdokhlebov

doi:10.1055/s-2007-990869

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

Alexey S. Degtyarenko^a, Andrey A. Tolmachev^b, Yulian M. Volovenko^a, 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;

Abstract

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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.

Key words

condensation - heterocycles - nitriles - quinolines - ring closure

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References

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