PDF herunterladen
Synthesis 2011(11): 1717-1722  
DOI: 10.1055/s-0030-1260043
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Facile and Quantitative Synthesis of 1,3-Diazaheterocycle-Fused 1,2,3-Triazole Derivatives Using Fluoroalkanesulfonyl Azide as a Diazo Transfer Reagent

Jiwei Gu, Wanting Xiong, Zhenhua Zhang, Shizheng Zhu*
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China
Fax: +86(21)64166128; e-Mail: zhusz@sioc.ac.cn;
Weitere Informationen

Publikationsverlauf

Received 28 February 2011
Publikationsdatum:
13. Mai 2011 (online)

    Lizenzen und Reprints Alle Artikel dieser Rubrik

Abstract

A series of 1,3-diazaheterocycle-fused 1,2,3-triazoles were conveniently and quantitatively prepared by 1,3-dipolar cycloaddition of heterocyclic ketene aminals with fluoroalkanesulfonyl azide, followed by elimination of fluoroalkanesulfonyl amide at room temperature without any catalyst.

Key words

fluoroalkanesulfonyl azide - ketene aminals - 1,3-dipolar cycloaddition - heterocycles - 1,3-diazaheterocycle-fused 1,2,3-triazole

    References

  • 1a Huang Z.-T. Wang M.-X. J. Org. Chem.  1992,  57:  184 
    Google Scholar
  • 1b Yan S.-J. Liu Y.-J. Chen Y.-L. Liu L. Lin J. Bioorg. Med. Chem. Lett.  2010,  20:  5225 
    Google Scholar
  • 1c Gladkov ES. Sirko SN. Shishkina SV. Shishkin OV. Knyazeva IV. Desenko SM. Chebanov VA. Monatsh. Chem.  2010,  141:  773 
    Google Scholar
  • 1d Pokhodylo NT. Matiychuk VS.
    J. Heterocycl. Chem.  2010,  47:  415 
    Google Scholar
  • 1e Bertelli L. Biagi G. Giorgi I. Livi O. Manera C. Scartoni V. Lucacchini A. Giannaccini G. Barili PL. Eur. J. Med. Chem.  2000,  35:  333 
    Google Scholar
  • 1f Liu B. Wang M.-X. Wang L.-B. Huang Z.-T. Heteroat. Chem.  2000,  11:  387 
    Google Scholar
  • 2a Cho S. Oh S. Um Y. Jung J.-H. Ham J. Shin W.-S. Lee S. Bioorg. Med. Chem. Lett.  2009,  19:  382 
    Google Scholar
  • 2b Zhang J.-J. Garrossian M. Gardner D. Garrossian A. Chang Y.-T. Kim YK. Tom Chang CW. Bioorg. Med. Chem. Lett.  2008,  18:  1359 
    Google Scholar
  • 2c Odlo K. Hentzen J. Chabert JF. Ducki S. Gani OABSM. Sylte I. Skrede M. Flørenes VA. Hansen TV. Bioorg. Med. Chem.  2008,  16:  4829 
    Google Scholar
  • 3a Genin MJ. Allwine DA. Anderson DJ. Barbachyn MR. Emmert DE. Garmon SA. Graber DR. Grega KC. Hester JB. Hutchinson DK. Morris J. Reischer RJ. Ford CW. Zurenko GE. Hamel JC. Schaadt RD. Stapert D. Yagi BH. J. Med. Chem.  2000,  43:  953 
    Google Scholar
  • 3b Thompson AM. Blaser A. Anderson RF. Shinde SS. Franzblau SG. Ma Z. Denny WA. Palmer BD. J. Med. Chem.  2009,  52:  637 
    Google Scholar
  • 3c Périon R. Ferrières V. García-Moreno MI. Mellet CO. Duval R. Fernández JMG. Plusquellec D. Tetrahedron  2005,  61:  9118 
    Google Scholar
  • 4 Fung-Tomc JC. Huczko E. Minassian B. Bonner DP. Antimicrob. Agents Chemother.  1998,  42:  313 
    Google Scholar
  • 5a Zhu S.-Z. J. Chem. Soc., Perkin Trans. 1  1994,  2077 
    Google Scholar
  • 5b Xu Y. Zhu S.-Z. Tetrahedron  1999,  55:  13725 
    Google Scholar
  • 5c Xu Y. Wang Y.-L. Zhu S.-Z. Zhu G.-Y. Jia Y.-S. Huang Q.-C. J. Fluorine Chem.  2000,  106:  133 
    Google Scholar
  • 5d Zhu S.-Z. Jin G.-F. Zhao J.-W. J. Fluorine Chem.  2003,  120:  65 
    Google Scholar
  • 5e He P. Zhu S.-Z. Tetrahedron  2006,  62:  549 
    Google Scholar
  • 5f Xu Y. Wang Y.-L. Zhu S.-Z. Synthesis  2000,  513 
    Google Scholar
  • 6a Huang Z.-T. Wamhoff H. Chem. Ber.  1984,  117:  622 
    Google Scholar
  • 6b Huang Z.-T. Wamhoff H. Chem. Ber.  1984,  117:  1856 
    Google Scholar
  • 6c Huang Z.-T. Wang X.-J. Tetrahedron Lett.  1987,  28:  1527 
    Google Scholar