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Synthesis 2009(11): 1865-1875  
DOI: 10.1055/s-0029-1216802
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Facile Synthesis of Fluorinated 1-Desazapurines

Viktor O. Iaroshenko*a,b, Dmitri V. Sevenardc, Dmitriy M. Volochnyuk*a,d, Yan Wange, Alexander Martilogab, Andrei O. Tolmacheva,b
a National Taras Shevchenko University, 62 Volodymyrska St., 01033 Kyiv-33, Ukraine
b ‘Enamine Ltd.’, 23 A. Matrosova St., 01103 Kyiv, Ukraine
Fax: +380(44)5373253; e-Mail: yaroshenko@enamine.net;
c Hansa Fine Chemicals GmbH, BITZ, Fahrenheitstraße 1, 28359 Bremen, Germany
d Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska 5, 02094 Kyiv-94, Ukraine
e-Mail: D.Volochnyuk@enamine.net;
e Fachbereich Chemie der Universität Konstanz, Fach M-720, Universitätsstraße 10, 78457 Konstanz, Germany
Further Information

Publication History

Received 3 December 2008
Publication Date:
12 May 2009 (online)

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Facile Synthesis of Fluorinated 1-DesazapurinesSynthesis 2009; 2009(11): e3-e3
DOI: 10.1055/s-0029-1216836

Abstract

A preparative approach towards 1-desazapurines, starting from 4(5)-aminoimidazoles and polyfluoroalkyl-containing 1,3-CCC-biselectrophiles was developed. As a result, a set of fluorinated 1-desazapurines was synthesized. Additionally, a synthetic route to 1-desazapurines bearing a sugar-mimicking group is proposed.

Key words

imidazoles - pyridines - annulations - fluorine - diketones - regioselectivity

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