Download PDF
Synthesis 2010(7): 1075-1077  
DOI: 10.1055/s-0029-1218656
SHORTPAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Novel Synthetic Approaches to (Trifluoromethyl)triazoles

Dmytriy A. Sibgatulina,b, Andrii V. Bezdudnya,b, Pavel K. Mykhailiuk*a,c, Nataliia M. Voievodaa,c, Ivan S. Kondratova,d, Dmitry M. Volochnyuka,b, Andrey A. Tolmacheva,c
a Enamine Ltd., Alexandra Matrosova Street 23, 01103 Kiev, Ukraine
Fax: +380(44)2351273; e-Mail: Pashamk@gmx.de;
b Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska Street 5, 02660 Kiev-94, Ukraine
c Department of Chemistry, Kiev National Taras Shevchenko University, Volodymyrska Street 64, 01033 Kiev, Ukraine
d Institute of Bioorganic Chemistry and Petrochemistry, National Academy of Sciences of Ukraine, Murmanska Street 1, 02660 Kiev-94, Ukraine
Further Information

Publication History

Received 26 November 2009
Publication Date:
29 January 2010 (online)

   Buy Article Permissions and Reprints All articles of this category

Abstract

New synthetic procedures for the trifluoromethyl-substituted triazoles, 3-(trifluoromethyl)-4H-1,2,4-triazole and 4-(trifluoromethyl)-1H-1,2,3-triazole, have been elaborated. The target compounds were prepared from commercially available trifluoro­acethydrazide (one step) and methyl propiolate (three steps), respectively.

Key words

fluorine - triazoles - trifluoromethyl group

    References

  • 1 Krivopalov VP. Shkurko OP. Russ. Chem. Rev. (Engl. Transl.)  2005,  74:  339 
    CrossrefGoogle Scholar
  • 2a Awad LF. El Ashry SH. Carbohydr. Res.  1998,  312:  9 
    Google Scholar
  • 2b Amir M. Shikha K. Eur. J. Med. Chem.  2004,  39:  535 
    Google Scholar
  • 2c Palaska E. Sahin G. Kelicen P. Durlu NT. Altinok G. Farmaco  2002,  57:  101 
    Google Scholar
  • 2d Holla BS. Poorjary KN. Rao BS. Shivananda MK. Eur. J. Med. Chem.  2002,  37:  511 
    Google Scholar
  • 2e Henichart JP. Houssin R. Berier JL. J. Heterocycl. Chem.  1986,  23:  1531 
    Google Scholar
  • 2f Demirbas N. Karaoglu SA. Demirbas A. Sancak K. Eur. J. Med. Chem.  2004,  39:  793 
    Google Scholar
  • 2g Demirbas N. Demirbas A. Karaoglu SA. Russ. J. Bioorg. Chem. (Engl. Transl.)  2005,  31:  387 
    Google Scholar
  • 3a O’Hagan D. Rzepa HS. Chem. Commun.  1997,  645 
    Google Scholar
  • 3b Kirsch P. Modern Fluoroorganic Chemistry   Wiley-VCH; Weinheim: 2004. 
    Google Scholar
  • 3c Qiu X.-L. Meng W.-D. Qing F.-L. Tetrahedron  2004,  60:  6711 
    Google Scholar
  • 4a Arban R. Benedetti R. Bonanomi G. Capelli A.-M. Castiglioni E. Contini S. Degiorgis F. Di Felice P. Donati D. Fazzolari E. Gentile G. Marchionni C. Marchioro C. Messina F. Micheli F. Oliosi B. Pavone F. Pasquarello A. Perini B. Rinaldi M. Sabbatini FM. Vitulli G. Zarantonello P. Di Fabio R. St-Denis Y. ChemMedChem  2007,  2:  528 
    Google Scholar
  • 4b Hager C. Miethchen R. Reinke H. J. Fluorine Chem.  2000,  104:  135 
    Google Scholar
  • 4c Stepanova NP. Orlova NA. Galishev VA. Turbanova ES. Petrov AA. Zh. Org. Khim.  1985,  21:  979 
    Google Scholar
  • 4d Stepanova NP. Galishev VA. Turbanova ES. Maleev AV. Potehin KA. Kurkutova EN. Struchkov YT. Petrov AA. Zh. Org. Khim.  1989,  25:  1613 
    Google Scholar
  • 5 Evans JJA, and Holan G. inventors; US  4038405.  ; Chem. Abstr. 1977, 87, 168041
  • 6 Crossman JM. Haszeldine RN. Tipping AE. J. Chem. Soc., Dalton Trans.  1973,  483 
    CrossrefGoogle Scholar
  • 7 Ye C. Gard GL. Winter RW. Syvret RG. Twamley B. Shreeve JM. Org. Lett.  2007,  9:  3841 
    CrossrefGoogle Scholar
  • 8 Bandera YP. Kanishchev OS. Timoshenko VM. But SA. Nesterenko AM. Shermolovich YG. Chem. Heterocycl. Compd. (Engl. Transl.)  2007,  43:  1138 
    CrossrefGoogle Scholar
  • 9 Dmowski W. In Houben-Weyl Methods of Organic Chemistry   Vol. E 10a:  Baasner B. Hagemann H. Tatlow JC. Georg Thieme; Stuttgart: 1999.  p.321 
    Google Scholar
  • 10 Sternfeld F. Carling RW. Jelley RA. Ladduwahetty T. Merchant KJ. Moore KW. Reeve AJ. Street LJ. O’Connor D. Sohal B. Atack JR. Cook S. Seabrook G. Wafford K. Tattersall FD. Collinson N. Dawson GR. Castro JL. MacLeod AM. J. Med. Chem.  2004,  47:  2176 
    CrossrefGoogle Scholar