Synthesis 2010(7): 1195-1199  
DOI: 10.1055/s-0029-1218657
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Noncatalytic Electrophilic Oxyalkylation of 3-Aminopyrazoles with 2-(Trifluoroacetyl)-1,3-azoles

Pavel V. Khodakovskiya,b, Pavel K. Mykhailiuk*a,b, Dmitriy M. Volochnyuka,c, Andrey A. Tolmacheva,b
a Enamine Ltd., Oleksandra Matrosova Street 23, 01103 Kyiv, Ukraine
b Department of Chemistry, Kyiv National Taras Shevchenko University, Volodymyrska Street 64, 01033 Kyiv, Ukraine
c Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska Street 5, 02660 Kyiv-94, Ukraine
Fax: +380(44)2351273; e-Mail: Pashamk@gmx.de;
Further Information

Publication History

Received 1 December 2009
Publication Date:
29 January 2010 (online)

Abstract

2-(Trifluoroacetyl)-1,3-azoles reacted with 3-aminopyrazoles to give the corresponding trifluoromethyl-substituted alcohols. The conditions required for the reaction and the yields of the products were highly dependent on the electronic nature of the both the 1,3-azole and the 3-aminopyrazole units.

    References

  • 1a O’Hagan D. Rzepa HS. Chem. Commun.  1997,  645 
  • 1b Kirsch P. Modern Fluoroorganic Chemistry   Wiley-VCH; Weinheim: 2004. 
  • 1c Smits R. Damiano Cadicamo C. Burger K. Koksch B. Chem. Soc. Rev.  2008,  37:  1727 
  • 1d Qiu X.-L. Meng W.-D. Qing F.-L. Tetrahedron  2004,  60:  6711 
  • 1e Dave R. Badet B. Meffre P. Amino Acids  2004,  24:  245 
  • 1f Fluorine-Containing Amino Acids   Kukhar VP. Soloshonok VA. Wiley; New York: 1995. 
  • 2a Harper DB. O’Hagan D. Nat. Prod. Rep.  1994,  123 
  • 2b Murphy CD. Schaffrath C. O’Hagan D. Chemosphere  2003,  455 
  • 3a Singh RP. Shreeve JM. Tetrahedron  2000,  56:  7613 
  • 3b Prakash GKS. Yudin AK. Chem. Rev.  1997,  97:  757 
  • 3c Umemoto T. Chem. Rev.  1996,  96:  1757 
  • 3d Burton DJ. Yang Z.-Y. Tetrahedron  1992,  48:  189 
  • 3e McClinton MA. McClinton DA. Tetrahedron  1992,  48:  6555 
  • 4a Lin P. Jiang J. Tetrahedron  2000,  56:  3635 
  • 4b Nenaidenko VG. Sanin AV. Balenkova ES. Russ. Chem. Rev.  1999,  68:  437 
  • 4c Bégué J.-P. Bonnet-Delpon D. Tetrahedron  1991,  47:  3207 
  • 4d Dolenský B. Kvíčala J. Paleček J. Paleta O. J. Fluorine Chem.  2002,  115:  67 
  • 4e Friezer RW. Ducharme Y. Ball RG. Blouin M. Boulet L. Côté B. Frenette R. Girard M. Guay D. Huang Z. Jones TR. Laliberté F. Lynch JJ. Mancini J. Martins E. Masson P. Muise E. Pon DJ. Siegl PKS. Styhler A. Tsou NN. Turner MJ. Young RN. Girard Y. J. Med. Chem.  2003,  46:  2413 
  • 4f Middleton L. J. Am. Chem. Soc.  1964,  86:  4948 
  • 4g Palecek J. Paleta O. Synthesis  2004,  521 
  • 4h Braun RA. J. Org. Chem.  1966,  31:  3828 
  • 4i Ohkura H. Berbasov DO. Soloshonok VA. Tetrahedron  2003,  59:  1647 
  • 5a Regel E. Buechel KH. Liebigs Ann. Chem.  1977,  145 
  • 5b Kawase M. Sakagami H. Kusama K. Motohashi N. Saito S. Bioorg. Med. Chem. Lett.  1999,  9:  3113 
  • 5c Fujii S. Maki Y. Kimoto H. J. Fluorine Chem.  1987,  35:  437 
  • 5d Salvador RL. Saucier M. Tetrahedron  1971,  27:  1221 
  • 6a Khodakovskiy PV. Volochnyuk DM. Panov DM. Pervak II. Zarudnitskii EV. Shishkin OV. Yurchenko AA. Shivanyuk A. Tolmachev AA. Synthesis  2008,  948 
  • 6b Khodakovskiy PV. Volochnyuk DM. Tolmachev AA. Synthesis  2009,  1099 
  • 6c Khodakovskiy PV. Volochnyuk V. Shivanyuk A. Shishkin OV. Tolmachev AA. Synthesis  2008,  3245 
  • 6d Khodakovskiy PV. Mykhailiuk PK. Volochnyuk DM. Tolmachev AA. Synthesis  2010, DOI: 10.1055/s-0029-1219219
  • 6e Khodakovskiy PV. Mykhailiuk PK. Volochnyuk DM. Tolmachev AA. Synthesis  2010, DOI: 10.1055/s-0029-1218633
  • 7 Pushechnikov AO. Volochnyuk DM. Tolmachev AA. Synlett  2002,  1140