Synthesis 2010(6): 967-970  
DOI: 10.1055/s-0029-1219219
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Noncatalytic Electrophilic Alkylation of 1H-Indole with 2-Trifluoroacetyl-1,3-heterazoles

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

Received 27 October 2009
Publikationsdatum:
04. Januar 2010 (online)

Abstract

A set of highly electrophilic 2-trifluoroacetyl-1,3-heterazoles demonstrated excellent activity in the C-hydroxyalkylation of 1H-indole. The reaction conditions and yields of the corresponding trifluoromethyl-substituted alcohols depend strongly on the electron-withdrawing nature of the 1,3-heterazole unit.

    References

  • 1a Singh RP. Shreeve JM. Tetrahedron  2000,  56:  7613 
  • 1b Prakash GKS. Yudin AK. Chem. Rev.  1997,  97:  757 
  • 1c Umemoto T. Chem. Rev.  1996,  96:  1757 
  • 1d Burton DJ. Yang Z.-Y. Tetrahedron  1992,  48:  189 
  • 1e McClinton MA. McClinton DA. Tetrahedron  1992,  48:  6555 
  • 2a Lin P. Jiang J. Tetrahedron  2000,  56:  3635 
  • 2b Nenaidenko VG. Sanin AV. Balenkova ES. Russ. Chem. Rev. (Engl. Transl.)  1999,  437 
  • 2c Bégué J.-P. Bonnet-Delpon D. Tetrahedron  1991,  47:  3207 
  • 3a Dolenský B. Kvíčala J. Paleček J. Paleta O. J. Fluorine Chem.  2002,  115:  67 
  • 3b 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 
  • 3c Middleton L. J. Am. Chem. Soc.  1964,  86:  4948 
  • 3d Palecek J. Paleta O. Synthesis  2004,  521 
  • 3e Braun RA. J. Org. Chem.  1966,  31:  3828 
  • 3f Ohkura H. Berbasov DO. Soloshonok VA. Tetrahedron  2003,  59:  1647 
  • 4a Regel E. Buechel KH. Justus Liebigs Ann. Chem.  1977,  145 
  • 4b Kawase M. Sakagami H. Kusama K. Motohashi N. Saito S. Bioorg. Med. Chem. Lett.  1999,  9:  3113 
  • 4c Fujii S. Maki Y. Kimoto H. J. Fluorine Chem.  1987,  35:  437 
  • 4d Salvador RL. Saucier M. Tetrahedron  1971,  27:  1221 
  • 5 Khodakovskiy PV. Volochnyuk DM. Panov DM. Pervak II. Zarudnitskii EV. Shishkin OV. Yurchenko AA. Shivanyuk A. Tolmachev AA. Synthesis  2008,  948 
  • 6a Khodakovskiy PV. Volochnyuk DM. Tolmachev AA. Synthesis  2009,  1099 
  • 6b Khodakovskiy PV. Volochnyuk V. Shivanyuk A. Shishkin OV. Tolmachev AA. Synthesis  2008,  3245 
  • 7a Masciadri R. Kamer M. Nock N. Eur. J. Org. Chem.  2003,  4286 
  • 7b Zhao J.-L. Liu L. Zhang H.-B. Wu Y.-C. Wang D. Chen YJ. Tetrahedron Lett.  2006,  47:  2511 
  • 7c Gilbert EE. J. Heterocycl. Chem.  1969,  6:  483