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

Pavel V. Khodakovskiy; Dmitriy M. Volochnyuk; Alexander Shivanyuk; Oleg V. Shishkin; Andrey A. Tolmachev

doi:10.1055/s-0028-1083150

PAPER

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

Pavel V. Khodakovskiy^a,b, Dmitriy M. Volochnyuk*^a,c, Alexander Shivanyuk^a,b, Oleg V. Shishkin^d, Andrey A. Tolmachev^b
^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

Abstract

All articles of this category

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.

Key words

Baylis-Hillman reaction - 1,3-azoles - Michael additions - trifluoromethyl substituted - allylic alcohols

Full Text

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.