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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 44, 2014 - Issue 6
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Original Articles

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

, , , &
Pages 788-799 | Received 26 Jun 2013, Published online: 20 Feb 2014
 

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.]

GRAPHICAL ABSTRACT

ACKNOWLEDGMENT

Financial support of this work by grant No. 20/2013 (specific university research) from the Ministry of Education, Youth and Sports of the Czech republic is gratefully acknowledged.

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