Synthesis of 2-(Arylsulfonyl)-4-hydroxypyridines by Hetero-Diels-Alder Reaction of 1,3-Bis-Silyl Enol Ethers with Arylsulfonyl Cyanides

Thomas Emmrich; Helmut Reinke; Peter Langer

doi:10.1055/s-2006-942446

PAPER

Synthesis of 2-(Arylsulfonyl)-4-hydroxypyridines by Hetero-Diels-Alder Reaction of 1,3-Bis-Silyl Enol Ethers with Arylsulfonyl Cyanides

Thomas Emmrich^a, Helmut Reinke^b, Peter Langer*^b,c
^a Institut für Biochemie, Universität Greifswald, Soldmannstr. 16, 17487 Greifswald, Germany
^b Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany
Fax: +49(381)4986412; e-Mail: peter.langer@uni-rostock.de;
^c Leibniz-Institut für Katalyse e. V., Universität Rostock , Albert-Einstein-Str. 29a, 18059 Rostock, Germany

Abstract

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Abstract

2-(Arylsulfonyl)-4-hydroxypyridines were prepared by Hetero-Diels-Alder reaction of 1,3-bis(trimethylsiloxy)buta-1,3-dienes (1,3-bis-silyl enol ethers) with arylsulfonyl cyanides. The products were transformed into 4-aryl-2-(arylsulfonyl)pyridines by Suzuki cross-coupling reactions of the corresponding enol triflates.

Key words

1,3-bis-silyl enol ethers - hetero-Diels-Alder - arylsulfonyl cyanide - pyridine

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References

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Crystallographic data (excluding structure factors) for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-295095(3c) and CCDC-297417(3e). Copies of this data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033 or e-mail: deposit@ccdc.cam.ac.uk) or via www.ccdc.cam.ac.uk/conts/retrieving.html.