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Electrophilic activation of acetyl-substituted heteroaromatic compounds
D A Klumpp1, M Garza, G V Sanchez
1Department of Chemistry, California State Polytechnic University, 3801 West Temple Avenue, Pomona, California 91768, USA. daklumpp@csupomona.edu
The Journal of Organic Chemistry
|January 10, 2001
Abstract:
The chemistry of acetyl-substituted pyridines, thiazoles, quinoline, isoquinolines, and pyrazine (1-9 and 28) has been studied. These heteroarenes (1-8) condense with benzene in good yields (74-96%) in the Bronsted superacid, CF(3)SO(3)H (triflic acid). In these acid-catalyzed hydroxyalkylation reactions, compounds 1-8 are significantly more reactive than acetophenone. It is proposed that compounds 1-8 readily form dicationic electrophiles in triflic acid.