Electrophilic activation of acetyl-substituted heteroaromatic compounds
DA Klumpp, M Garza, GV Sanchez, S Lau… - The Journal of …, 2000 - ACS Publications
DA Klumpp, M Garza, GV Sanchez, S Lau, S de Leon
The Journal of Organic Chemistry, 2000•ACS PublicationsThe 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, CF3SO3H (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.
pyrazine (1− 9 and 28) has been studied. These heteroarenes (1− 8) condense with
benzene in good yields (74− 96%) in the Bronsted superacid, CF3SO3H (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.
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, CF3SO3H (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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