Reactions of Benzenediazonium Ions with Adenine and Its Derivatives

Article abstract of DOI:10.1021/jo00324a001

Adenine, adenosine, and 5'-adenylic acid react readily with benzenediazonium ion and its derivatives at pH 8-11 to yield derivatives of (E)-6-(3-phenyl-2-triazen-1-yl)purine.The structural assignments for these compounds, some of which are unstable, are based on their spectroscopic properties and their degradation reactions in acid solution and with sodium dithionite to yield 6-hydrazinopurine.The triazenes decompose in basic aqueous solution at 60-90 deg C to produce 8-aryladenines.For adenosine and 5'-adenylic acid, the ribose residues are cleaved during this process.Several lines of evidence indicate that the triazenes are converted to 8-aryladenines in intermolecular processes.Both the benzenediazonium ion and the phenyl radical can be intercepted during the reaction.Consequently, the phenylation reaction may be confidently formulated as an intermolecular free-radical substitution reaction.