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Abstract
Abstract Direct arylation of adenine with fluoro- and chloronitrobenzenes leads to mixtures of N9 and N7 substituted adenines. After separation by column chromatography, the individual isomers can be efficiently hydrogenated on Pd to give the corresponding aminophenyladenines. A significant enhancement of the reaction rate by microwave irradiation was observed. This two-step procedure was found to be a feasible route to otherwise hardly available 7-aminophenyladenines. Correlation between calculated shielding constants and experimental values of chemical shifts in 13C and 15N NMR was used for assignment of the site of substitution. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resource(s): Full experimental and spectral details.]
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