SYNTHESIS OF 5-ARYLTHIOURIDINES VIA ELECTROPHILIC SUBSTITUTION OF 5-BROMOURIDINES WITH DIARYL DISULFIDES

Novel synthetic method of 5-arylthiouridine derivatives is described. Treatment of 5-bromo-2',3'-O-isopropylideneuridine (la) with diaryl di sulfides in the presence of sodium hydride at ambient temperature gave the 5-arylthiouridines (2) in participation of the 5'-hydroxy group o nto the uracil ring and the electrophilic nature of diaryl disulfide, which was applied to the synthesis of 5-arylthio-1-beta-D-arabinofuran osyluracils (8).