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

抄録

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 II₁, 6-methoxy-(II₂), 6-phenoxy-(II₃), 6-anilino (III₁), 6-(2-furfurylamino)-(III₂), and 6-hydrazino-9-phenyl-9H-purine (III₃). I also reacts with pyrrole in the presence of sodium amide to form 6-(1-pyrrolyl)-9-phenyl-9H-purine (III₄). 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 (IV₁), ethyl α-cyano-9-phenyl-9H-purine-6-acetate (IV₂), α, 9-diphenyl-9H-purine-6-acetonitrile (IV₃), 3-(9-phenyl-9H-purin-6-yl)-2, 4-pentanedione (IV₄), and 2-(9-phenyl-9H-purin-6-yl) acetophenone (IV₅). This reaction can be utilized for introduction of a carbon chain into the 6-position of the purine ring.