Reaction of 5-Carboxypyrimidine Derivatives with Sodium Bisulfite:A Facile Decarboxylation Method

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Abstract

5-Carboxyuracil derivatives were shown to react with aqueous sodium bisulfite in mild condition resulting in facile decarboxylation to give corresponding 5-decarboxy-5, 6-dihydrouracil-6-sulfonates and uracils in good yield. The former compounds were quantitatively transformed to the latter in alkaline condition. Mechanistic feature of this reaction was discussed, which implied the initial nucleophilic addition of bisulfite across the 5, 6-double bond. 5-Carboxycytosine was also shown to react similarly, however, accompanied by hydrolytic deamination.

Journal

  • Agricultural and Biological Chemistry

    Agricultural and Biological Chemistry 36(9), 1571-1579, 1972

    Japan Society for Bioscience, Biotechnology, and Agrochemistry

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