Synthesis 2006(15): 2551-2555  
DOI: 10.1055/s-2006-942446
PAPER
© Georg Thieme Verlag Stuttgart · New York

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

Thomas Emmricha, Helmut Reinkeb, 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
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Publikationsverlauf

Received 2 February 2006
Publikationsdatum:
28. Juni 2006 (eFirst)

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.

    References

  • 1a Boger DL. Weinreb SM. Hetero-Diels-Alder Methodology in Organic Synthesis   Academic Press; San Diego CA: 1987. 
  • 1b Tietze LF. Schneider C. J. Org. Chem.  1991,  56:  2476 
  • 2 For cycloaddition reactions of nitriles, see: Collier S. Langer P. In Science of Synthesis   Shinkai I. Murahashi S. Thieme; Stuttgart: 2004.  Chap. 19.5.15.
  • 3 Breitmaier E. Rüffer U. Synthesis  1989,  623 
  • Sulfonyl cyanides have been used as electrophilic cyanation reagents, see:
  • 4a Christophersen C. Begrup M. Ebdrup S. Petersen H. Vedsoe P. J. Org. Chem.  2003,  68:  9513 
  • 4b Boymond L. Rottlaender M. Cahiez G. Knochel P. Angew. Chem. Int. Ed.  1998,  37:  1701 
  • 4c Jensen T. Teiler J. Waernmark K. J. Org. Chem.  2002,  67:  6008 
  • 5 Wang T. Hendrickson J. Org. Prep. Proced. Int.  2003,  35:  623 
  • 6 van Leusen AM. Jagt JC.   , 
  • 7 McClure CK. Link JS. J. Org. Chem.  2003,  68:  8256 
  • 8 For a review of 1,3-bis-silyl enol ethers, see: Langer P. Synthesis  2002,  441 
  • 9a Hirokawa Y. Horikawa T. Kato S. Chem. Pharm. Bull.  2000,  48:  1847 
  • 9b Cutshall NS. Ursino R. Kucera KA. Latham J. Ihle NC. Bioorg. Med. Chem. Lett.  2001,  14:  1951 
  • 9c Bonnet V. Mongin F. Trecourt F. Queguiner G. Knochel P. Tetrahedron  2002,  58:  4429 
  • 9d Ohnmacht CJ. Russell K. Empfield JR. Frank CA. Gibson KH. J. Med. Chem.  1996,  39:  4592 
  • 9e Yogi S. Hokama K. Tsuge O. Bull. Chem. Soc. Jpn.  1987,  60:  335 
  • 9f Reiffenrath V. Bremer M. Angew. Chem., Int. Ed. Engl.  1994,  33:  1386 ; Angew. Chem. 1994, 106, 1435
  • 9g Furukawa N. Tsuruoka M. Fujihara H. Heterocycles  1986,  24:  3337 
  • 10 Molander GA. Cameron KO. J. Am. Chem. Soc.  1993,  115:  830 
  • 11 Anderson G. Cameron DW. Feutrill GI. Read RW. Tetrahedron Lett.  1981,  22:  4347 
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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.