Electrophilic activation of acetyl-substituted heteroaromatic compounds |
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Authors: | Klumpp D A Garza M Sanchez G V Lau S de Leon S |
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Affiliation: | Department of Chemistry, California State Polytechnic University, 3801 West Temple Avenue, Pomona, California 91768, USA. daklumpp@csupomona.edu |
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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. |
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