Direct Arylation of Adenine by Fluoro-and Chloronitrobenzenes: Effect of Microwaves

Article abstract of DOI:10.1080/00397911.2013.831902

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.]