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Synfacts 2008(11): 1141-1141  
DOI: 10.1055/s-0028-1083492
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

An Undemanding Synthesis of Thiazolo[4,5-d]pyridines

Contributor(s): Victor Snieckus, Timothy Hurst
V. O. Iaroshenko, D. M. Volochnyuk*, N. V. Kryvokhyzha, A. Martyloga, D. V. Sevenard, U. Groth, J. Brand, A. N. Chernega, A. N. Shivanyuk, A. A. Tolmachev
Universität Konstanz and Hansa Fine Chemicals GmbH, Bremen, Germany; National Academy of Sciences of Ukraine, National Taras Shevchenko University and Enamine Ltd., Kyiv, Ukraine; University of Glasgow, UK
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Publication History

Publication Date:
23 October 2008 (online)

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Significance

The synthesis of thiazolo[4,5-d]pyridines from 5-unsubstituted 4-aminothiazole derivatives 1 or 2 and fluorine-containing 1,3-diketones 3 is described. In many cases the products were obtained as a single isomer 4 in good to excellent yield, although mixtures of regioisomers 4 and 5 were observed in some cases. A one-pot synthesis of thiazolo[4,5-d]pyridines 7 was also developed from thioureas 6, although giving only moderate yields. A wide range of functional group tolerance was shown for both processes.