Abstract
AbstractThe 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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