Elsevier

Tetrahedron Letters

Volume 52, Issue 4, 26 January 2011, Pages 505-508
Tetrahedron Letters

One-pot copper-catalyzed tandem addition–cyclization of 2-iodoanilines with isoselenocyanates for the practical preparation of 2-aminobenzoselenazoles

https://doi.org/10.1016/j.tetlet.2010.11.092Get rights and content

Abstract

A convenient and successful one-pot preparation of the 2-aminobenzoselenazoles via the phenylselenoureas has been accomplished by the copper-catalyzed ligand-free reaction of the 2-iodoanilines and isoselenocyanates; the intermediate, selenoureas, were isolated, and quantitatively transformed into the selenazaoles.

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Acknowledgments

This work was supported in part by a Grant-in Aid for Scientific Research from the Ministry of Education, Science and Culture, Japan (19590022). Thanks are due to Mr. Koki Fujii (Hokuriku University) for his technical assistance.

References and notes (18)

  • H. Sashida et al.

    Tetrahedron Lett.

    (2010)
  • E.A. Jaseer et al.

    Tetrahedron Lett.

    (2010)
    D.S. Bose et al.

    Tetrahedron Lett.

    (2007)
    D.S. Bose et al.

    J. Org. Chem.

    (2006)
    X. Huang et al.

    Tetrahedron

    (2003)
    N.K. Downer-Riley et al.

    Tetrahedron

    (2008)
    J. Garin et al.

    Synth. Commun.

    (1990)
  • D.R. Garud et al.

    Molecules

    (2007)
    H. Heimgartner et al.

    Phosphorus Sulfur Silicon Relat. Elem.

    (2008)
    M. Ninomiya et al.

    Heterocycles

    (2010)
  • H. Sashida et al.

    Synthesis

    (2010)
  • H. Sashida et al.

    Synthesis

    (2008)
    H. Sashida et al.

    Heterocycles

    (2010)
    H. Sashida et al.

    Molecules

    (2010)
    Sashida, H.; Kaname, M.; Ohyanagi, K. Heterocycles, in press,...H. Sashida et al.

    Tetrahedron

    (2010)
  • G.M. Sheldrick

    shelxl-97, Program for Crystal Structure Refinement

    (1997)
  • D.A. Horton et al.

    Chem. Rev.

    (2003)
    X. Deng et al.

    Eur. J. Org. Chem.

    (2010)
  • J. Easmon et al.

    J. Med. Chem.

    (2006)
    D. Kumar et al.

    Bioorg. Med. Chem.

    (2002)
    M.L. Kantam et al.

    Synlett

    (2009)
    A.B. Naidu et al.

    Synthesis

    (2010)
There are more references available in the full text version of this article.

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