Synthesis 2008(20): 3245-3252  
DOI: 10.1055/s-0028-1083150
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Baylis-Hillman Reactions of 2-(Trifluoroacetyl)-1,3-azoles

Pavel V. Khodakovskiya,b, Dmitriy M. Volochnyuk*a,c, Alexander Shivanyuka,b, Oleg V. Shishkind, Andrey A. Tolmachevb
a Enamine Ltd., 23 A. Matrosova st., 01103 Kyiv, Ukraine
Fax: +380(44)5373253; e-Mail: D.Volochnyuk@enamine.net;
b National Taras Shevchenko University, 62 Volodymyrska st., 01033 Kyiv-33, Ukraine
c Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska 5, 02094 Kyiv-94, Ukraine
d Institute for Scintillation Materials, National Academy of Sciences of Ukraine, 60 Lenina Avenue, 61001 Kharkiv, Ukraine
Further Information

Publication History

Received 8 May 2008
Publication Date:
25 September 2008 (online)

Abstract

2-(Trifluoroacetyl)-1,3-azoles readily react with methyl acrylate and acrylonitrile under Baylis-Hillman reaction conditions to afford heterocyclic trifluoromethyl-containing allylic alcohols in 36-97% yields. The thus obtained Baylis-Hillman adducts readily undergo Michael addition reactions with various nucleophiles.

    References

  • 1a Basavaiah D. Venkateswara Rao K. Reddy RJ. Chem. Soc. Rev.  2007,  36:  1581 
  • 1b Basavaiah D. Jaganmohan Rao A. Satyanarayana T. Chem. Rev.  2003,  103:  811 
  • 2a CF3 Ketones: Golubev AS. Kolomiets AF. Fokin AV. J. Fluorine Chem.  1991,  54:  , 272 
  • 2b Isatins, ninhydrin: Chung YM. Im YJ. Kim JN. Bull. Korean Chem. Soc.  2002,  23:  1651 
  • 3 Common ketones: Hill JS. Isaacs NS. Tetrahedron Lett.  1986,  27:  5007. 
  • 4 Khodakovskiy PV. Volochnyuk DM. Panov DM. Pervak II. Zarudnitskii EV. Shishkin OV. Yurchenko AA. Shivanyuk A. Tolmachev AA. Synthesis  2008,  948 
  • 5 For analogous transformation of BH products see: Batra S. Roy AK. Patra A. Bhaduri AP. Surin WR. Raghavan SAV. Sharma P. Kapoor K. Dikshit M. Bioorg. Med. Chem.  2004,  12:  2059 
6

Sheldrick, G. M. SHELXTL PLUS, PC Version; a system of computer programs for the determination of crystal structure from X-ray diffraction data; Rev.5.1, 1998.