1972 Volume 36 Issue 9 Pages 1571-1579
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.
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