Synthesis and some properties of 6-β-oxoalkyl(aralkyl, hetaralkyl, cycloalkyl)thiopurines
PM Kochergin, MY Gromov, EV Aleksandrova… - Chemistry of …, 1993 - Springer
PM Kochergin, MY Gromov, EV Aleksandrova, SY Skachilova
Chemistry of Heterocyclic Compounds, 1993•SpringerThe reaction of 6-purinethione with α-haloketones has given a series of new 6-β-oxoalkyl
(aralkyl, hetaralkyl, cycloalkyl) thiopurines. Their alkylation in position 9 and acid hydrolysis
to hypoxanthine and its 9-alkyl derivatives has been studied. The hydrolysis of the acetals of
6-formylmethylthiopurine and the oxidation of 6-(2, 3-dihydroxypropyl) thiopurine leads to 6-
formylmethylthiopurine, which shows a ring-chain tautomerism and exists in the form of 7-
hydroxy-7, 8-dihydrothiazolo [2, 3-i] purine.
(aralkyl, hetaralkyl, cycloalkyl) thiopurines. Their alkylation in position 9 and acid hydrolysis
to hypoxanthine and its 9-alkyl derivatives has been studied. The hydrolysis of the acetals of
6-formylmethylthiopurine and the oxidation of 6-(2, 3-dihydroxypropyl) thiopurine leads to 6-
formylmethylthiopurine, which shows a ring-chain tautomerism and exists in the form of 7-
hydroxy-7, 8-dihydrothiazolo [2, 3-i] purine.
Abstract
The reaction of 6-purinethione with α-haloketones has given a series of new 6-β-oxoalkyl(aralkyl, hetaralkyl, cycloalkyl)thiopurines. Their alkylation in position 9 and acid hydrolysis to hypoxanthine and its 9-alkyl derivatives has been studied. The hydrolysis of the acetals of 6-formylmethylthiopurine and the oxidation of 6-(2,3-dihydroxypropyl)thiopurine leads to 6-formylmethylthiopurine, which shows a ring-chain tautomerism and exists in the form of 7-hydroxy-7,8-dihydrothiazolo[2,3-i]purine.
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