Download PDF
Synlett 2010(12): 1771-1774  
DOI: 10.1055/s-0030-1258117
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

1,2,4-Triazole Synthesis via Amidrazones

Laurent El Kaim*, Marion Gizzi, Laurence Grimaud*
Laboratoire Chimie et Procédés, Ecole Nationale Supérieure de Techniques Avancées, 32 Boulevard Victor, 75739 Paris Cedex 15, France
Fax: +33(1)45528322; e-Mail: laurent.elkaim@ensta.fr; e-Mail: laurence.grimaud@ensta.fr;
Further Information

Publication History

Received 13 April 2010
Publication Date:
30 June 2010 (online)

    Permissions and Reprints All articles of this category

Abstract

We present a two-step procedure for the synthesis of 1,2,4-triazole derivatives from a primary amide and a hydrazine via an oxidative process.

Key words

triazoles - hydrazone - oxidation

    References

  • 1a Punniyamurthy T. Velusamy S. Iqbal J. Chem. Rev.  2005,  105:  2329 
    Google Scholar
  • 1b Punniyamurthy T. Rout L. Coord. Chem. Rev.  2008,  252:  134 
    Google Scholar
  • 1c Marko IE. Giles PR. Tsukazaki M. Gautier A. Dumeunier R. Dodo K. Philippart F. Chelle-Regnault I. Mutonkole J.-L. Brown SM. Urch CJ. Aerobic, Metal-Catalyzed Oxidation of Alcohols, Transition Metals for Organic Synthesis   Vol. 2:  Wiley-VCH; Weinheim: 2004.  p.437-478  
    Google Scholar
  • 1d Samec SM. Ell AH. Backvall J.-E. Chem. Eur. J.  2005,  11:  2327 
    Google Scholar
  • 2a Mirica LM. Ottenwaelder X. Stack TDP. Chem. Rev.  2004,  104:  1013 
    Google Scholar
  • 2b Lewis EA. Tolman WB. Chem. Rev.  2004,  104:  1047 
    Google Scholar
  • 2c Schultz MJ. Sigman MS. Tetrahedron  2006,  62:  8227 
    Google Scholar
  • 2d Stahl SS. Angew. Chem. Int. Ed.  2004,  43:  3400 
    Google Scholar
  • 2e Kotov V. Scarborough CC. Stahl SS. Inorg. Chem.  2007,  46:  1910 
    Google Scholar
  • 2f Wu L. Qiu S. Liu G. Org. Lett.  2009,  11:  2707 
    Google Scholar
  • 2g Wurtele C. Sander O. Lutz V. Waitz T. Tuczek F. Schindler S.
    J. Am. Chem. Soc.  2009,  131:  7544 
    Google Scholar
  • 3a Nakamichi N. Kawashita Y. Hayashi M. Org. Lett.  2002,  4:  3955 
    Google Scholar
  • 3b Walton JC. Scott JS. Portella-Cubillo F. J. Org. Chem.  2008,  73:  5558 
    Google Scholar
  • 3c Palacios F. Alonso C. Amezua P. Rubiales G. J. Org. Chem.  2002,  67:  1941 
    Google Scholar
  • 3d Padwa A. Austin DJ. Precedo L. Zhi L. J. Org. Chem.  1993,  58:  1144 
    Google Scholar
  • 3e Bora U. Saikia A. Boruah RC. Org. Lett.  2003,  5:  435 
    Google Scholar
  • 4a Atlan V. El Kaim L. Lacroix S. Morgentin R. Chem. Commun.  1999,  1893 
    Google Scholar
  • 4b Atlan V. El Kaim L. Supiot C. Chem. Commun.  2000,  1385 
    Google Scholar
  • 4c Atlan V. Bienaymé H. El Kaim L. Majee A. Chem. Commun.  2000,  1585 
    Google Scholar
  • 4d El Kaim L. Grimaud L. Perroux Y. Tirla C. J. Org. Chem.  2003,  68:  8733 
    Google Scholar
  • 5 El Kaim L. Grimaud L. Jana NK. Mettetal F. Tirla C. Tetrahedron Lett.  2002,  43:  8925 
    CrossrefGoogle Scholar
  • 6a Buzykin BI. Bredikhina ZA. Synthesis  1993,  59 
    Google Scholar
  • 6b Paulvannan K. Chen T. Hale R. Tetrahedron  2000,  56:  8071 
    Google Scholar
  • For reviews, see:
  • 7a Neilson DG. Roger R. Heatlie JWM. Newlands LR. Chem. Rev.  1970,  151 
    Google Scholar
  • 7b Watson KM. Neilson DG. In The Chemistry of Amidines and Imidates   Patai S. Interscience; London: 1975.  p.491-545  
    Google Scholar
  • 8a Shawali AS. Osman A. Tetrahedron  1971,  27:  2517 
    Google Scholar
  • 8b Drutkowski G. Donner C. Schulze I. Frohberg P. Tetrahedron  2002,  58:  5317 
    Google Scholar
  • 9a Smith RF. Johnson DS. Abgott RA. Madden MJ. J. Org. Chem.  1973,  38:  1344 
    Google Scholar
  • 9b Manley PJ. Bilodeau MT. Org. Lett.  2002,  4:  3127 
    Google Scholar
  • 10 For further oxidative preparation of 1,2,4-triazoles from hydrazones, see: Ciesielski M. Pufky D. Döring M. Tetrahedron  2005,  61:  5942 
    CrossrefGoogle Scholar