Synthesis of Thiazolo[4,5-d]pyridines

Viktor O. Iaroshenko; Dmitriy M. Volochnyuk; Nadiya V. Kryvokhyzha; Aleksander Martyloga; Dmitri V. Sevenard; Ulrich Groth; Jörg Brand; Alexander N. Chernega; Alexander N. Shivanyuk; Andrei A. Tolmachev

doi:10.1055/s-2008-1067152

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Synthesis 2008(15): 2337-2346
DOI: 10.1055/s-2008-1067152

PAPER

Synthesis of Thiazolo[4,5-d]pyridines

Viktor O. Iaroshenko^a,c, Dmitriy M. Volochnyuk*^b,f, Nadiya V. Kryvokhyzha^d, Aleksander Martyloga^c,f, Dmitri V. Sevenard^e, Ulrich Groth^a, Jörg Brand^a, Alexander N. Chernega^b, Alexander N. Shivanyuk^c,f, Andrei A. Tolmachev^c
^a Fachbereich Chemie, Universität Konstanz, Fach M-720, Universitätsstraße 10, 78457 Konstanz, Germany
^b Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska 5, 02094 Kyiv-94, Ukraine
Fax: +380(44)5373253; e-Mail: D.Volochnyuk@enamine.net;
^c National Taras Shevchenko University, 62 Volodymyrska St., 01033 Kyiv-33, Ukraine
^d Department of Chemistry, University of Glasgow, University Avenue, Glasgow G12 8QQ, UK
^e Hansa Fine Chemicals GmbH, BITZ, Fahrenheitstraße 1, 28359 Bremen, Germany
^f ‘Enamine Ltd.’, 23 A. Matrosova St., 01103 Kyiv, Ukraine

Further Information

Publication History

Received 24 February 2008
Publication Date:
18 June 2008 (online)

Abstract
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Abstract

The reaction of 2-aminothiazol-4(5H)-iminium salts with various 1,3-CCC-dielectrophiles was investigated. As a result, a set of diverse thiazolo[4,5-d]pyridines were obtained. The scope and limitation of the approach is described.

Key words

thiazoles - pyridines - annulation - fluorine - diketones - regioselectivity

References

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Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Center as supplementary publications CCDC 677236 and 677237 and 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.