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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
Further Information

Publication History

Received 27 October 2009
Publication Date:
04 January 2010 (online)

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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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