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Purines XIV . . Reactivity of 8‐bromo‐3,9‐dimethylxanthine towards some nucleophilic reagents
Author(s) -
Youssef Shaker,
Pfleiderer Wolfgang
Publication year - 1998
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570350428
Subject(s) - chemistry , nucleophile , reactivity (psychology) , reagent , sigmatropic reaction , medicinal chemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology
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.