Pyrenes undergo initial electrophilic substitution in the 1
position; a second substitution typically
occurs in the 3, 6, or 8 positions. We sought a pyrene with
synthetically useful handles in the
unusual 2,7 substitution pattern. To that end,
7-amino-2-pyrenecarboxylic acid was prepared by
partial reduction of pyrene to 4,5,9,10-tetrahydropyrene,
Friedel−Crafts acylation in the 2 position,
and conversion to 2-carbethoxytetrahydropyrene through the haloform
reaction and esterification.
Nitration of the ester proceeded in the 7 position;
rearomatization, reduction of the nitro group,
and saponification gave the title compound.
7-Amino-2-pyrenecarboxylic Acid.-The title compound (XII) is a useful synthon for the preparation of biochemically interesting pyrenes and for monolayered films. -(MUSA, A.; SRIDHARAN, B.; LEE, H.; MATTERN, D. L.; J.
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