Journal of Heterocyclic Chemistry p. 949 - 954 (1998)
Update date:2022-08-29
Topics:
Youssef, Shaker
Pfleiderer, Wolfgang
The reactivity of 8-bromo-3,9-dimethylxanthine (6) towards a variety of nucleophilic reagents has been investigated. Nucleophilic displacements take place easily with aliphatic mercaptans and aliphatic alcohols, whereas aliphatic amines required more severe conditions. Prolonged heating of 6 with amines causes a new type of rearrangement from 3,9- to 3,7-dimethylxanthines due to a 1,3-sigmatropic shift of the N(9)-methyl group.
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