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 language | English |
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Pages (from-to) | 2259-2266 |
Number of pages | 8 |
Journal | Tetrahedron |
Volume | 33 |
Issue number | 17 |
DOIs | |
State | Published - 1977 |