题名：5-HYDROXYPYRIMIDINES I.SYNTHESIS OF 2-SUBSTITUTED 4,5,6-TRIHYDROXYPYRIMIDINES

摘要：he chemistry of 5-hydroxylated pyrimidines and their preparative methods were briefly reviewed. A route leading to the synthesis of 5-hydroxypyrimidines was suggested and was typified by a successful synthesis of various 2-substituted 4,5,6-trihydroxypyrimidines. Claisen condensation of ethyl benzyloxyacetate with ethyl oxalate followed by thermal removal of carbon monoxide yielded ethyl benzyloxymalonate, which was caused to condense with various amidine derivatives to give differently 2-substituted 4,6-dihydroxy-5-benzyloxypyrimidines, the 2-substituents being hydroxyl, amino, methyl, thiol and ethylthio groups. Raney nickel desulphurization of 2-thiol compound gave the 2-unsubstituted derivative without affecting the benzyl group. The benzyl group was then hydrogenolyzed and the corresponding 2-unsubstituted 4,5,6-trihydroxypyrimidines were obtained in quantitative yields.The aromatic character of 5-hydroxyl group in these pyrimidines is reflected by their colour reaction with ammoniacal ferric chloride, barium hydroxide and phosphomolybdic acid solutions. In virtue of their common enediol structure, they decolourize 2,6-dichlorophenolindophenol solution.

作者：张滂、伍少兰

来源（出处）： Science in China,Ser.A 1957年第2期、《张滂文集》

发表日期：2000年8月