Synthesis of 6-C-Substituted 9-Tetrahydrofuranylpurine Derivatives

6-Dicyanomethylene-9-tetrahydrofuranylpurine (4), which was obtained by the reaction of 9H-1, 6-dihydropurine-Δ6, α-propanedinitrile (3) with 2, 3-dihydrofuran, has been catalytically hydrogenated to the α-(aminomethylene)-9-(tetrahydrofuran-2-yl)-9H-purine-6-acetonitrile (5) in good yield using N,...

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Veröffentlicht in:Chemical & pharmaceutical bulletin 1990/07/25, Vol.38(7), pp.2018-2019
Hauptverfasser: HAMAMICHI, Norimitsu, MIYASAKA, Tadashi
Format: Artikel
Sprache:eng
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Zusammenfassung:6-Dicyanomethylene-9-tetrahydrofuranylpurine (4), which was obtained by the reaction of 9H-1, 6-dihydropurine-Δ6, α-propanedinitrile (3) with 2, 3-dihydrofuran, has been catalytically hydrogenated to the α-(aminomethylene)-9-(tetrahydrofuran-2-yl)-9H-purine-6-acetonitrile (5) in good yield using N, N-dimethylformamide-benzene as a solvent over Pd-C under medium pressure. Substitution of 5 with amines gave the corresponding alkylaminomethylene purines (6 and 7). Reaction of 5 with hydrazine gave the pyrazole derivative (8).
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.38.2018