Purine誘導体に関する研究(第2報)6-(Methylsulfonyl)-9-phenyl-9H-purineについて

概要

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Heating of 6-(methylsulfonyl)-9-phenyl-9H-purine (1) with dilute sulfuric acid or acetic acid results in its decomposition into 9-phenyl-9H-purin-6-ol (II). The methylsulfonyl group in I easily undergoes nucleophilic substitution with hydroxide, methoxide, phenoxide, aniline, 2-furfurylamine, and hydrazine to respectively form II_1,6-methoxy-(II_2), 6-phenoxy-(II_3), 6-anilino (III_1), 6-(2-furfurylamino)-(III_2), and 6-hydrazino-9-phenyl-9H-purine (III_3). I also reacts with pyrrole in the presence of sodium amide to form 6-(1-pyrrolyl)-9-phenyl-9H-purine (III_4). I also reacts with malononitrile, ethyl cyanoacetate, phenylacetonitrile, acetylacetone, and acetophenone in dimethyl sulfoxide, in the presence of potassium hydroxide, to respectively afford 9-phenyl-9H-purine-6-malononitrile (IV_1), ethyl α-cyano-9-phenyl-9H-purine-6-acetate (IV_2), α, 9-diphenyl-9H-purine-6-acetonitrile (IV_3), 3-(9-phenyl-9H-purin-6-yl)-2,4-pentanedione (IV_4), and 2-(9-phenyl-9H-purin-6-yl) acetophenone (IV_5). This reaction can be utilized for introduction of a carbon chain into the 6-position of the purine ring.
社団法人日本薬学会の論文
1979-02-25