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Synthesis 2009(22): 3869-3879  
DOI: 10.1055/s-0029-1216995
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Reactions of 3-(Polyfluoroacyl)chromenones with Heterocyclic Amines: Novel Synthesis of Polyfluoroalkyl-Containing Fused Pyridines

Anton Kotljarova,b, Viktor O. Iaroshenko*c,d, Dmitriy M. Volochnyukc, Roman A. Irgasheve, Vyacheslav Ya. Sosnovskikhe
a Formaly Fachbereich Chemie der Universität Konstanz, Fach M-720, Universitätsstr. 10, 78457 Konstanz, Germany
b Institute of Organic and Bioorganic Chemistry, University of Tartu, Jakobi 2, 50014 Tartu, Estonia
c Enamine Ltd., 23 A. Matrosova st., 01103 Kyiv, Ukraine
Fax: +380(44)5373253; e-Mail: yaroshenko@enamine.net;
d National Taras Shevchenko University, 62 Volodymyrska st., 01033 Kyiv 33, Ukraine
e Department of Chemistry, Ural State University, 51 Lenina Ave., 620083 Ekaterinburg, Russian Federation
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Publication History

Received 19 May 2009
Publication Date:
08 September 2009 (online)

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Abstract

The selectivity of the reactions of 3-(polyfluoroacyl)-4H-chromen-4-ones with a wide range of aminoheterocycles and arylamines has been evaluated. The method described facilitates access to polyfluoroalkyl-containing fused pyridines.

Key words

aminoheterocycles - arylamines - condensation - chroman-4-ones - polyfluoroalkyl - fused pyridines

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Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 721116 for 3n, CCDC 721117 for 4a, and CCDC 721118 for 5g can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44 (1223)336033; e-mail: deposit@ccdc.cam.ac.uk].