A novel bimolecular disproportionation in purine-N-oxides. A spontaneous autocatalytic and an anhydride induced disproportionation of 8-alkyl-7-hydroxyxanthines

Gury Zvilichovsky*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

8-Alkyl-7-hydroxyxanthines undergo in aqueous solution, near pH 5, an unusual spontaneous autocatalytic disproportionation. They yield the corresponding 8-alkylxanthines as the reduction product and 6-amino-5-nitrosouracil as the oxidation product. The disproportionation can also be induced by anhydrides at pH 4-12. The alkyl group at position 8 is essential for these reactions. Possible mechanisms are discussed.

Original languageEnglish
Pages (from-to)2259-2266
Number of pages8
JournalTetrahedron
Volume33
Issue number17
DOIs
StatePublished - 1977

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