Abstract
Reaction of 5-Bromo-1,3,6-trimethyluracil (1) with alkylthiolate (propane-1-, toluene-α-, allyl-, etc.) ions under phase transfer catalytic conditions follows nucleophilic substitution and X-philic (Br and S) elimination to give 5-alkylthio-1,3,6-trimethyluracils, 6-alkylthiomethyl-1,3-dimethyluracils and 1,3,6-trimethyluracil. Reaction of compound 1 with heteroarylthiolate ions (pyridine-2-, quinazoline-4-, uracil-2- and 4,6-dimethylpyrimidine-2-thiolate) gives only nucleophilic substitution products. However, arylthiolate (phenyl-, 4-chlorophenyl-, 2-aminophenyl-) ions follow a single electron transfer (SET) mechanism to give 5-arylthio-6-arylthiomethyl-1,3-dimethyluracils along with normal substitution products. 1,3,6-Trimethyluracil does not react with alkyl- or heteroaryl-thiolate ions but reacts with arylthiolate ions (SET) providing mainly 5-arylthio-1,3,6-trimethyluracils. 5-Bromo-1,3,6-trimethyturacil( 1 ) with alkylthiolate ions under PTC follow nucleophilic substitution and X-philic elimination. 1 with heteroarylthiolate ions give only nucleophilic substitution products, but, with arylthiolate ions follow single electron transfer (SET) mechanism.
Published Version
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