核酸ピリミジン塩基ならびにそのアナローグの1-Cyclohexy1置換体の合成 : N-ヘテロ芳香族の電子的性状第25報

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Studies have been carried on the syntheses of 1-cyclohexyl derivatives of uracil, 5-bromouracil, thymine, cytosine, 4-thiouracil, and 2,4-dithiouracil. 1-Cyclohexyluracil (V) was synthesized through dehydrogenation of 1-cyclohexyl-5,6-dihydrouracil (III) which was obtained by treating ethyl N-cyclohexyl-β-alaninate with potassium cyanate in acid medium. 1-Cyclohexyl-5-bromouracil (VII) was prepared by dehydrobromination of 5,5-dibromo derivative of III. 1-Cyclohexylthymine (XII) was synthesized by dehydrogenation of 1-cyclohexyl-5,6-dihydrothymine (X) obtained through cyclization of methyl N-cyclohexyl-β-aminoisobutylate (IX). Thiation of V gave 1-cyclohexyl-4-thiouracil (XIII), which was treated further with alcoholic ammonia in a sealed tube to yield 1-cyclohexylcytosine (XIV). XIII was also obtained by dehydrogenation of 1-cyclohexyl-5,6-dihydrothiouracil (XVI) derived from III. We describe then the ultraviolet spectrophotometric properties of 1-cyclohexylsubstituted pyrimidines thus obtained.
社団法人日本薬学会の論文
1968-09-25