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

Anton Kotljarov; Roman A. Irgashev; Viktor O. Iaroshenko; Dmitri V. Sevenard; Vyacheslav Ya. Sosnovskikh

doi:10.1055/s-0029-1216957

PAPER

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

Anton Kotljarov^a,b, Roman A. Irgashev^c, Viktor O. Iaroshenko*^d,e, Dmitri V. Sevenard^f, Vyacheslav Ya. Sosnovskikh^c
^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

Abstract

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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

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