Purines. LXXIII. Syntheses of 8-Alkoxy- and 8-Hydroxy-3-alkyladenines from 3-Alkyladenine 7-Oxides through 7-Alkoxy-3-alkyladenines
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概要
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7-Alkoxy-3-alkyladenine perchlorates (9) were prepared from 3-alkyladenines (4) by N-oxidation followed by alkylation with alkyl halides in N, N-dimethylacetamide. The 7-methoxy derivatives 9d, g, j thus obtained afforded 3-methyl-8-hydroxyadenine (7a), 3-ethyl-8-hydroxyadenine (7b), and 3-benzyl-8-hydroxyadenine (7c) in 74%, 72%, and 39% yields, respectively, on treatment with boiling 0.1 N aqueous sodium hydroxide, whereas treatment of 9d, g, j with sodium methoxide in methanol at room temperature afforded 3-alkyl-8-methoxyadenines (10m, p, q) in 91%-98% yields. Similar treatment of 9d with sodium ethoxide in ethanol afforded 8-ethoxy-3-methyladenine (10n) in 89% yield. Compounds 10m, q were alternatively prepared from 9d, j in 77% and 84% yields, respectively, by treatment with 0.1 N aqueous sodium hydroxide in the presence of methanol. This method was suitable for the synthesis of the 8-benzyloxy compound 10o : it was obtained in 60% yield by treating 7-benzyloxy-3-methyladenine perchlorate (9f) with a mixture of aqueous sodium hydroxide and benzyl alcohol. Compounds 7 were alternatively prepared from 9 through 10. For example, 7c was obtained in 84% overall yield by treatment of 9j with sodium methoxide, followed by hydrolysis of the resulting 10q with boiling 1 N hydrochloric acid.On the other hand, methylation of 3-methyladenine 7-oxide (8a) with dimethyl sulfate in 0.1 N aqueous sodium hydroxide in the absence or presence of added methanol afforded N^6,3-dimethyladenine 7-oxide (14) in 13% or 14% yield, together with 7a (4% yield) or 10m (11%).
- 公益社団法人日本薬学会の論文
- 1996-11-15
著者
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ITAYA Taisuke
Faculty of Pharmaceutical Sciences, Kanazawa University
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Itaya Taisuke
Faculty Of Pharmaceutical Sciences Kanazawa University
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TAKADA Yasutaka
Faculty of Pharmaceutical Sciences, Kanazawa University
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FUJII Tozo
Faculty of Pharmaceutical Sciences, Kanazawa University
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Fujii Tozo
Faculty Of Pharmaceutical Sciences Kanazawa University
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Takada Yasutaka
Faculty Of Pharmaceutical Sciences Kanazawa University
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TAKEDA Yasutaka
Faculty of Pharmaceutical Sciences, Kanazawa University
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Takeda Yasutaka
Faculty Of Pharmaceutical Sciences Kanazawa University
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