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.
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