Purines. VII. 1-Alkoxy-9-alkyladenine Salts as Possible Alkylating Reagents
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概要
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Treatment of 1-methoxy-9-methyladenine hydriodide (Ia) with hot pyridine has been found to produce 1-methylpyridinium salt (IIf) and 9-methyladenine 1-oxide (IIIf). Similarly, pyridine was ethylated with 1-ethoxy-9-benzyladenine hydriodide (Ic) to give 1-ethylpyridinium iodide (IIg : X=I) and 9-benzyladenine 1-oxide (IIIh). Benzyl alcohol was possible to be methylated with 1-methoxy-9-benzyladenine hydriodide (Ib), although yield of benzyl methyl ether was poor. Reactions of 1-benzyloxy-9-benzyladenine hydrobromide (Id) with various nucleophiles such as pyridine, aniline, C_2H_5S-, CH_3CO_2-, ethanol, and water also proceeded smoothly and yielded the corresponding benzylated products and IIIh in good yields. Benzylation of adenine with Id in N, N-dimethylacetamide at 35° furnished 3-benzyl-adenine as the major product and 9-benzyladenine and 1-benzyladenine as the minor products. The reactivities of Id toward pyridine and ethanol have been compared with those of 1-benzyloxy-9-benzyladenine perchlorate (Ie), and possible mechanisms of the alkylation with 1-alkoxyadenine derivatives (type I) are discussed.
- 公益社団法人日本薬学会の論文
- 1972-05-25
著者
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藤井 澄三
Faculty Of Pharmaceutical Sciences Kanazawa University
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板谷 泰助
Faculty of Pharmaceutical Sciences, Kanazawa University
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茂籠 哲
Faculty Of Pharmaceutical Sciences Kanazawa University
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