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■ The Reactions of Benzenediazonium Ions with Some Purines and Pyrimidines

Ming-Hong Hung and Leon M. Stock*

*Department of Chemistry, University of Chicago, 5735 South Ellis Avenue, Chicago, IL 60637, U.S.A.

Abstract

The reactions of certain pyrimidines and purines with benzenediazonium ions in basic solution have been investigated to determine whether the reactions provide triazenes, azo coupling, or phenylation products. Under these conditions, the anion of uracil forms the 5-azo coupling product. No reaction occurs with the anion of uridine or 5’-uridylic acid. A complex mixture of products is obtained with cytosine, but cytidine and 5’-cytidylic acid fail to yield either azo coupling or phenylation products. Xanthine readily undergoes the 8-arylazo coupling reaction. Xanthosine is unreactive. In contrast, inosine yields 8-phenylinosine. Purine itself is converted to 6-phenylpurine. The structure of the product was proved by deuterium labeling experiments. The factors governing the reactivity of these compounds are briefly noted.