Download PDF
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;
Further Information

Publication History

Received 28 February 2011
Publication Date:
13 May 2011 (online)

   Permissions and Reprints All articles of this category
Preview

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 
    Search in Google Scholar
  • 1b Yan S.-J. Liu Y.-J. Chen Y.-L. Liu L. Lin J. Bioorg. Med. Chem. Lett.  2010,  20:  5225 
    Search in Google Scholar
  • 1c Gladkov ES. Sirko SN. Shishkina SV. Shishkin OV. Knyazeva IV. Desenko SM. Chebanov VA. Monatsh. Chem.  2010,  141:  773 
    Search in Google Scholar
  • 1d Pokhodylo NT. Matiychuk VS.
    J. Heterocycl. Chem.  2010,  47:  415 
    Search in 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 
    Search in Google Scholar
  • 1f Liu B. Wang M.-X. Wang L.-B. Huang Z.-T. Heteroat. Chem.  2000,  11:  387 
    Search in 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 
    Search in 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 
    Search in 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 
    Search in 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 
    Search in 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 
    Search in Google Scholar
  • 3c Périon R. Ferrières V. García-Moreno MI. Mellet CO. Duval R. Fernández JMG. Plusquellec D. Tetrahedron  2005,  61:  9118 
    Search in Google Scholar
  • 4 Fung-Tomc JC. Huczko E. Minassian B. Bonner DP. Antimicrob. Agents Chemother.  1998,  42:  313 
    Search in Google Scholar
  • 5a Zhu S.-Z. J. Chem. Soc., Perkin Trans. 1  1994,  2077 
  • 5b Xu Y. Zhu S.-Z. Tetrahedron  1999,  55:  13725 
    Search in 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 
    Search in Google Scholar
  • 5d Zhu S.-Z. Jin G.-F. Zhao J.-W. J. Fluorine Chem.  2003,  120:  65 
    Search in Google Scholar
  • 5e He P. Zhu S.-Z. Tetrahedron  2006,  62:  549 
    Search in Google Scholar
  • 5f Xu Y. Wang Y.-L. Zhu S.-Z. Synthesis  2000,  513 
  • 6a Huang Z.-T. Wamhoff H. Chem. Ber.  1984,  117:  622 
    Search in Google Scholar
  • 6b Huang Z.-T. Wamhoff H. Chem. Ber.  1984,  117:  1856 
    Search in Google Scholar
  • 6c Huang Z.-T. Wang X.-J. Tetrahedron Lett.  1987,  28:  1527 
    Search in Google Scholar