Purines. VIII. : Reactions of 1-Benzoyl-1, 6-dihydro-9-phenyl-9H-purine-6-carbonitrile (9-Phenylpurine Reissert Compound) with Acid, Bases, and Electrophiles

抄録

1-Benzoyl-1, 6-dihydro-9-phenyl-9H-purine-6-carbonitrile(1, 9-phenylpurine Reissert compound) was hydrolyzed in an acid medium to give the ring fission product of the pyrimidine ring (3, 4). Alkaline hydrolysis of 1 gave 9-phenyl-9H-purine (2) and benzoic acid (5). The anion of 1 generated from 1 and sodium hydride in tetrahydrofuran underwent aromatization, resulting in the formation of 9-phenyl-9H-purine-6-carbonitrile (6) together with 2. The reaction of 1 with aromatic aldehydes in the presence of sodium hydride proceeded to give the 6-purinylmethyl benzoates (8a-c), together with 2 and 9. On the other hand, the reaction of 1 with 2, 4-dinitrochlorobenzene in the presence of sodium hydride failed to give the corresponding 6-arylpurine, and the aromatization product 6 was obtained.