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

Pavel V. Khodakovskiy; Pavel K. Mykhailiuk; Dmitriy M. Volochnyuk; Andrey A. Tolmachev

doi:10.1055/s-0029-1219219

PAPER

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

Pavel V. Khodakovskiy^a,b, Pavel K. Mykhailiuk*^a,b, Dmitriy M. Volochnyuk^a,c, Andrey A. Tolmachev^a,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

Abstract

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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.

Key words

1,3-heterazoles - alkylations - trifluoromethyl alcohols - indoles - electrophilic additions

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References

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