Synthesis of 5-Arylthiouridines via Electrophilic Substitution of 5-Bromouridines with Diaryl Disulfides |
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Authors: | Kosaku Hirota Tetsuo Tomishi Yoshifumi Maki Hironao Sajiki |
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Institution: | Laboratory of Medicinal Chemistry , Gifu Pharmaceutical University , Mitahora-higashi, Gifu, 502, Japan |
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Abstract: | Abstract Novel synthetic method of 5-arylthiouridine derivatives is described. Treatment of 5-bromo-2′,3′-O-isopropylideneuridine (1a) with diaryl disulfides in the presence of sodium hydride at ambient temperature gave the 5-arylthiouridines (2) in moderate yields. The present method is devised by virtue of a combination of efficient participation of the 5′-hydroxy group onto the uracil ring and the electrophilic nature of diaryl disulfide, which was applied to the synthesis of 5-arylthio-1-β-D-arabinofuranosyl-uracils (8). |
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