79982-46-0

Upstream product

• 6118-33-8 p-sulfobenzenediazonium chloride 
• 61-19-8 5'-adenosine monophosphate 
• 121-57-3 4-aminobenzene sulfonic acid 
• 77079-61-9 C₁₆H₁₇BrN₇O₇P 

Relevant academic research and scientific papers

Reactions of Benzenediazonium Ions with Guanine and Its Derivatives

Guanine reacts with several benzenediazonium ions rapidly in aqueous solution at pH 10.5 to form 8-(arylazo)guanines in good yield.The reaction of guanine with 4-bromobenzenediazonium ion forms ε-guanine about 50-fold more rapidly than the reaction of adenine with this ion to yield 6-purine under these experimental conditions.Guanosine reacts much more slowly than guanine with the benzenediazonium ions in aqueous solution at pH 8.5 or 10.5 to give 8-arylguanosines.The structures of these products were established by their spectroscopic properties and by their quantitative conversion to 8-arylguanines. 5'-Guanylic acid also reacts quite slowly with the benzenediazonium ions in aqueous solution at pH 10.5.Only the compounds with strong electron-withdrawing groups yield N-2 triazenes at ambient temperature.No 8-aryl or 8-arylazo compounds are formed with 5'-guanylic acid at this temperature.However, 4-bromo- and 4-sulfobenzenediazonium ions react with 5'-guanylic acid at higher temperatures to yield the 8-aryl-5'-guanylic acids in low yield.The structures of these products were proven by hydrolysis to 8-arylguanines.The 8-arylguanosines and the 8-aryl-5'-guanylic acids are formed via free-radical phenylation reactions.The factors governing the reactivity of the adenines and the guanines are discussed.

Reactions of Benzenediazonium Ions with Adenine and Its Derivatives

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.