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Synthesis 2009(19): 3233-3242  
DOI: 10.1055/s-0029-1216957
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

3-(Polyfluoroacyl)chromones and Their Hetero Analogues as Valuable Substrates for Syntheses of 4-(Polyfluoroalkyl)pyrimidines

Anton Kotljarova,b , Roman A. Irgashevc, Viktor O. Iaroshenko*d,e, Dmitri V. Sevenardf, Vyacheslav Ya. Sosnovskikhc
a Fachbereich Chemie, Universität Konstanz, Fach M-720, Universitätsstr. 10, 78457 Konstanz, Germany
b Institute of Organic and Bioorganic Chemistry, University of Tartu, Jakobi 2, 51014 Tartu, Estonia
c Department of Chemistry, Ural State University, pr. Lenina 51, 620083 Ekaterinburg, Russian Federation
d Enamine Ltd, 23 A. Matrosova st., 01103 Kyiv, Ukraine
Fax: +380(44)5373253; e-Mail: yaroshenko@enamine.net;
e National Taras Shevchenko University, 62 Volodymyrska st., Kiev-33, 01033, Ukraine
f Hansa Fine Chemicals GmbH, BITZ, Fahrenheitstr. 1, 28359 Bremen, Germany
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Publication History

Received 23 February 2009
Publication Date:
21 August 2009 (online)

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Abstract

Reactions of 3-(polyfluoroacyl)chromones and their hetero analogues with a number of 1,3-NCN-dinucleophiles, such as amidines or guanidines, were studied in detail, and preparative access to a set of diverse 5-salicyloyl-4-(polyfluoroalkyl)pyrimidines was elaborated. These compounds appear to be a suitable starting substrates for the synthesis of 4-(polyfluoroalkyl)pyrimidine-5-carboxylic acids or pyrimidines containing a benzofuran-3-yl substituent in the 5-position.

Key words

chromones - thiochromones - fluorine - pyrimidine core annulation - regioselectivity - heterocycles