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Synlett 2007(7): 1043-1046  
DOI: 10.1055/s-2007-973875
LETTER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 3-Sulfonyloxypyridines: Oxidative Ring Expansion of α-Furyl­sulfonamides and N→O Sulfonyl Transfer

Robert Hodgsona, Andrew Kennedyb, Adam Nelson*a, Alexis Perry*a
a Department of Chemistry, University of Leeds, Leeds, LS2 9JT, UK
Fax: +44(113)3436565; e-Mail: a.s.nelson@leeds.ac.uk; e-Mail: oldralph@hotmail.co.uk;
b Synthetic Chemistry, Chemical Development, GlaxoSmithKline, Gunnels Wood Road, Stevenage, Hertfordshire, SG1 2NY, UK
Further Information

Publication History

Received 4 December 2006
Publication Date:
13 April 2007 (online)

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Abstract

N-Sulfonyl pyridinones derived from α-furylsulfon­amides may be aromatised with concomitant N→O sulfonyl transfer to produce 3-sulfonyloxypyridines.

Key words

furans - pyridines - rearrangements - ring expansion - ­sulfonamides

    References

  • Some recent examples include:
  • 1a Warshakoon NC. Wu S. Boyer A. Kawamoto R. Sheville J. Bhatt RT. Renock S. Xu K. Pokross M. Zhou S. Walter R. Mekel M. Evdokimov AG. East S. Bioorg. Med. Chem. Lett.  2006,  16:  5616 
    CrossrefGoogle Scholar
  • 1b Thomas SA. Li T. Woods KW. Song X. Packard G. Fisher JP. Diebold RB. Liu X. Shi Y. Klinghofer V. Johnson EF. Bouska JJ. Olson A. Guan R. Magnone SR. Marsh K. Luo Y. Rosenberg SH. Giranda VL. Li Q. Bioorg. Med. Chem. Lett.  2006,  16:  3740 
    CrossrefGoogle Scholar
  • 1c Wang X. Zhi B. Baum J. Chen Y. Crockett R. Huang L. Eisenberg S. Ng J. Larsen R. Martinelli M. Reider P. J. Org. Chem.  2006,  71:  4021 
    CrossrefGoogle Scholar
  • 1d Iso Y. Grajkowska E. Wroblewski JT. Davis J. Goeders NE. Johnson KM. Sanker S. Roth BL. Tueckmantel W. Kozikowski AP. J. Med. Chem.  2006,  49:  1080 
    CrossrefGoogle Scholar
  • 1e Hartz RA. Arvanitis AG. Arnold C. Rescinito JP. Hung KL. Zhang G. Wong H. Langley DR. Gilligan PJ. Trainor GL. Bioorg. Med. Chem. Lett.  2006,  16:  934 
    CrossrefGoogle Scholar
  • 2a Sacchetti JC. Blanchard JS. Res. Microbiol.  1996,  147:  36 
    CrossrefPubMedGoogle Scholar
  • 2b Dorsey BD. Levin RB. McDaniel SL. Vacca JP. Guare JP. Darke PL. Zugay JA. Emini EA. Schleif WA. Quintero JC. Lin JH. Chen I.-W. Holloway MK. Fitzgerald PMD. Axel MG. Ostovic D. Anderson PS. Huff JR. J. Med. Chem.  1994,  37:  3443 
    CrossrefPubMedGoogle Scholar
  • 3a Karig G. Spencer JA. Gallagher T. Org. Lett.  2001,  3:  835 
    CrossrefGoogle Scholar
  • 3b Trécourt F. Marsais F. Güngör T. Quéguiner G. J. Chem. Soc., Perkin Trans. 1  1990,  2409 
    CrossrefGoogle Scholar
  • 3c Bonnet V. Mongin F. Trécourt F. Quéguiner G. J. Chem. Soc., Perkin Trans. 1  2000,  4245 
    CrossrefGoogle Scholar
  • 4 Zhang TY. Stout JR. Keay JG. Scriven EFV. Toomey JE. Goe GL. Tetrahedron  1995,  51:  13177 
    CrossrefGoogle Scholar
  • 5 Lemire A. Grenon M. Pourashraf M. Charette AB. Org. Lett.  2004,  6:  3517 
    CrossrefGoogle Scholar
  • 6 Sanders EB. Secor HV. Seeman JI. J. Org. Chem.  1976,  41:  2659 
    CrossrefGoogle Scholar
  • 7 Cvetovich RJ. Reamer RA. DiMichele L. Chung JYL. Chilenski JR. J. Org. Chem.  2006,  71:  8610 
    CrossrefGoogle Scholar
  • 8 Fernández Sainz Y. Raw SA. Taylor RJK. J. Org. Chem.  2005,  70:  10086 
    CrossrefGoogle Scholar
  • 9a Elming N. Clauson-Kass N. Acta Chem. Scand.  1956,  10:  1603 
    Google Scholar
  • 9b Mavoungou-Gomes L. Bull. Soc. Chim. Fr.  1967,  5:  1764 
    Google Scholar
  • 9c Kuo Y.-H. Shih K.-S. Chem. Pharm. Bull.  1991,  39:  181 
    Google Scholar
  • 10 Maeba I. Suzuki M. Takahashi N. Iijima T. Furukawa H. J. Heterocycl. Chem.  1988,  25:  503 
    Google Scholar
  • 11 Müller C. Diehl V. Lichtenthaler FW. Tetrahedron  1998,  54:  10703 
    CrossrefGoogle Scholar
  • 12 For an isolated example of this process, see: Hodgson R. Majid T. Nelson A. J. Chem. Soc., Perkin Trans. 1  2002,  1631 
    CrossrefGoogle Scholar
  • 13a Fu X. Zhang S. Yin J. McAllister TL. Jiang SA. Tann C.-H. Thiruvengadam TK. Zhang F. Tetrahedron Lett.  2002,  43:  573 
    CrossrefGoogle Scholar
  • 13b Zim D. Lando VR. Dupont J. Monteiro AL. Org. Lett.  2001,  3:  3049 
    CrossrefGoogle Scholar
  • 14 Davis FA. Zhang Y. Andemichael Y. Fang T. Fanelli DL. Zhang H. J. Org. Chem.  1999,  64:  1403 
    CrossrefGoogle Scholar
  • 15 Zhou W.-S. Lu Z.-H. Wang Z.-M. Tetrahedron  1993,  49:  2641 
    CrossrefGoogle Scholar
  • 16 Burke MD. Berger EM. Schreiber SL. Science  2003,  302:  613 
    CrossrefGoogle Scholar
  • 17 Höfle G. Steglich W. Vorbrüggen H. Angew. Chem., Int. Ed. Engl.  1978,  17:  569 
    CrossrefGoogle Scholar