title: Electrophilic activation of acetyl-substituted heteroaromatic compounds.
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.
authors.affiliation: Department of Chemistry, California State Polytechnic University, 3801 West Temple Avenue, Pomona, California 91768, USA. daklumpp@csupomona.edu
authors.forename: D A
authors.initials: DA
authors.lastname: Klumpp
authors.forename: M
authors.initials: M
authors.lastname: Garza
authors.forename: G V
authors.initials: GV
authors.lastname: Sanchez
authors.forename: S
authors.initials: S
authors.lastname: Lau
authors.forename: S
authors.initials: S
authors.lastname: de Leon
mesh_terms: D000098:Acetophenones; D000107:Acetylation; D000478:Alkylation; D002384:Catalysis; D006571:Heterocyclic Compounds / Q000737:chemistry*; D007202:Indicators and Reagents; D008698:Mesylates / Q000737:chemistry
chemical_list: D000098:Acetophenones; D006571:Heterocyclic Compounds; D007202:Indicators and Reagents; D008698:Mesylates; C012077:trifluoromethanesulfonic acid