Journal of heterocyclic chemistry

Purines XIV.. Reactivity of 8??bromo??3, 9??dimethylxanthine towards some nucleophilic reagents

S Youssef, W Pfleiderer

Index: Youssef, Shaker; Pfleiderer, Wolfgang Journal of Heterocyclic Chemistry, 1998 , vol. 35, # 4 p. 949 - 954

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Citation Number: 29

Abstract

Abstract 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.