REGIOSELECTIVE SYNTHESES OF 5- AND 6-AMINOANTHRACENE-2,3-DIMETHANOL

Abstract We report the regioselective synthesis of 6-amino-2,3-anthracenedimethanol ( 2 ) beginning from commercially available 2,3-dimethylanthraquinone. The more reactive 9- and 10- positions of the anthracene core are masked from electrophilic attack by “protection” of the molecule through formation of its corresponding ethano anthracene (“barrelane”) adduct. Also reported is the synthesis of the corresponding 5-amino isomer ( 1 ) from readily available anthraquinone-2,3-dicarboxylic acid.