S. Senda, K. Hirota, J. Notani
Jul 25, 1972
Citations
0
Influential Citations
5
Citations
Journal
Chemical & Pharmaceutical Bulletin
Abstract
When 1-substituted 5-cyanouracils, 3-substituted 5-cyanouracils or 1, 3-disubstituted 5-cyanouracils (substituents : phenyl, cyclohexyl, methyl) were heated to reflux in conc. HBr, the cyano group in the 5-position was removed and 1-substituted, 3-substituted or 1, 3-disubstituted uracils were obtained, respectively. When warmed with conc. H2SO4, they gave 5-carbamoyluracil derivatives. Refluxing of the 5-carbamoyluracil derivatives with conc. HCl in AcOH, produced 5-carboxyuracil derivatives. Detailed consideration was made on mechanism of hydrolysis and decarboxylation of 5-cyanouracil derivatives under acidic conditions. Furthermore, hydrolysis of 5-cyanouracils under alkaline conditions was investigated.