Electrophilic activation of acetyl-substituted heteroaromatic compounds.
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.
Klumpp
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Department of Chemistry, California State Polytechnic University, 3801 West Temple Avenue, Pomona, California 91768, USA. daklumpp@csupomona.edu
Garza
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Sanchez
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Lau
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de Leon
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D000098:Acetophenones; D000107:Acetylation; D000478:Alkylation; D002384:Catalysis; D006571:Heterocyclic Compounds / Q000737:chemistry*; D007202:Indicators and Reagents; D008698:Mesylates / Q000737:chemistry
D000098:Acetophenones; D006571:Heterocyclic Compounds; D007202:Indicators and Reagents; D008698:Mesylates; C012077:trifluoromethanesulfonic acid