Regioselective Synthesis of
Novel Perfluoroalkylated Fused Pyridines and 3-(Aminomethylene)thiochroman-4-ones
from 3-(Perfluoroalkanoyl)thio­chromenones and Amines

Anton Kotljarov; Dmitri V. Sevenard; Viktor O. Iaroshenko; Roman A. Irgashev; Dmitriy M. Volochnyuk; Peter Langer; Andrei A. Tolmachev; Vyacheslav Ya. Sosnovskikh

doi:10.1055/s-0029-1218586

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Synthesis 2010(4): 671-677
DOI: 10.1055/s-0029-1218586

PAPER

Regioselective Synthesis of Novel Perfluoroalkylated Fused Pyridines and 3-(Aminomethylene)thiochroman-4-ones from 3-(Perfluoroalkanoyl)thiochromenones and Amines

Anton Kotljarov^a,b, Dmitri V. Sevenard^c, Viktor O. Iaroshenko*^d,e, Roman A. Irgashev^f, Dmitriy M. Volochnyuk^d, Peter Langer^g, Andrei A. Tolmachev^d,e, Vyacheslav Ya. Sosnovskikh*^f
^a Formerly 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 Hansa Fine Chemicals GmbH, BITZ, Fahrenheitstr. 1, 28359 Bremen, Germany
^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., Kyiv 33, 01033, Ukraine
^f Department of Chemistry, Ural State University, 51 Lenina Ave., 620083 Ekaterinburg, Russian Federation
e-Mail: Vyacheslav.Sosnovskikh@usu.ru;
^g Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany

Further Information

Publication History

Received 3 September 2009
Publication Date:
07 December 2009 (online)

Abstract
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Abstract

The regioselectivity of reactions of 3-(perfluoroacyl)-4H-thiochromen-4-ones with a range of hetaryl, aryl, and alkyl amines was examined. The reactions provide ready access to polyfluoroalkylated fused pyridines and thiochromen-4-ones.

Key words

heterocycles - amines - fused-ring systems - thiochromenones - perfluoroalkyl compounds

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