Purines. XXIII. Synthesis of N^6-Alkoxy-1,3-dialkyladeninium Salts and an Attempt to Synthesize 1,3-Dimethyladenine
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概要
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Ethylation of N^6-methoxy-3-methyladenine (5) with EtI in AcNMe_2 gave the 1-ethylated product 8 (X=I) (21% yield) and the N^6-ethylated product 11 (X=ClO_4) (33%). The N^6-benzyloxy analogue 6,prepared from 3-methyl-6-methylthiopurine (4) and benzyloxyamine, was similarly methylated to produce the 1-methylated product 9 (X=Cl) (34%) as well as the N^6-methylated product 12 (X=Cl) (35%). Reduction of N^6-methoxy-1,3-dimethyladeninium iodide (7 : X=I) with NaBH_4 afforded the 1,2-dihydro derivative 14 (92% yield), which reverted to 7 (X=I) on dehydrogenation with I_2 in EtOH. On hydrogenation with Raney Ni and H_2,7 (X=I) furnished 14 (26% yield) and the N^6-demethoxy derivative 15・HI (17%), while 14 gave 15 on similar reduction. Dehydrogenation of 15 with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) in CHCl_3 yielded a crude solid presumed to be the 1,3-dimethyladeninium salt (18), which readily rearranged into N^6,3-dimethyladenine (16) through the monocycle 17. It has been found that hydrolysis of 7 (X=ClO_4) to give the imidazole 13 in H_2O at pH 7.72 and 25℃ proceeds ca. 270 times as fast as that of the 3,9-dimethyl analogue 19 to give the monocycle 20.
- 公益社団法人日本薬学会の論文
- 1983-10-25
著者
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斎藤 徹
Faculty Of Pharmaceutical Sciences Kanazawa University
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中坂 剛志
Faculty of Pharmaceutical Sciences, Kanazawa University
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中坂 剛志
Faculty Of Pharmaceutical Sciences Kanazawa University
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