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Synthesis 2007(20): 3163-3170  
DOI: 10.1055/s-2007-990791
PAPER
© Georg Thieme Verlag Stuttgart · New York

Chlorotrimethylsilane-Mediated Synthesis of 2-Aryl-1-chloro-1-heteroarylalkenes

Sergey V. Ryabukhina,b, Andrey S. Plaskona,b, Dmitriy M. Volochnyuk*a,c, Andrey A. Tolmachevb
a Enamine Ltd., 23 Alexandra Matrosova st., 01103 Kiev, Ukraine
b National Taras Shevchenko University, 62 Volodymyrska st., 01033 Kiev, Ukraine
c Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska 5, 02094 Kiev, Ukraine
Fax: +380(44)5373253; e-Mail: D.Volochnyuk@enamine.net;
Further Information

Publication History

Received 3 June 2007
Publication Date:
21 September 2007 (online)

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Abstract

The condensation of (chloromethyl)heterarenes with aro­matic aldehydes was investigated, resulting in a simple and flexi­ble general procedure for the synthesis of 2-aryl-1-chloro-1-heteroarylalkenes. The best reaction conditions were found to be heating in N,N-dimethylformamide in the presence of chlorotri­methylsilane as a promoter and water-scavenger.

Key words

(chloromethyl)heterocycles - aromatic aldehydes - Knoevenagel­ condensation - 2-aryl-1-halo-1-heteroarylalkene - chlorotrimethylsilane

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