Purines. XXX. : Ring Fission of 3,7-Dialkyladenines by Alkaline Hydrolysis
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概要
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On treatment with boiling 1 N aqueous NaOH for 2 h, 3,7-dialkyladenine salts (7 : R^1,R^2=Me, Et, or PhCH_2; X=Br, I, or ClO_4) gave 1-alkyl-4-(N-alkylamino)-1H-imidazole-5-carboxamides (8), 1-alkyl-4-amino-1H-imidazole-5-carboxamides (11), and N^6,7-dialkyladenines (14) in 33-59%, 2-10%, and 2-5% yields, respectively. Under slightly miler reaction conditions, 3,7-dimethyl-adenine hydriodide (7a : X=I) afforded 1-methyl-4-(N-methylamino)-1H-imidazole-5-carboxamide (8a) together with 3,7-dimethylhypoxanthine (2a) as a by-product; 7-benzyl-3-methyladenine hydrobromide (7c : X=Br) furnished a small amount of 1-benzyl-4-(N-methylamino)-1H-imidazole-5-carboxamidine (5c) besides 1-benzyl-4-(N-methlamino)-1H-imidazole-5-carboxamide (8c), 1-benzyl-4-amino-1H-imidazole-5-carboxamide (11c), and 7-benzyl-N^6-methyladenine (14c). These results are best interpreted in terms of pathways involving hydrolytic deamination, ring fission in the pyrimidide and imidazole moieties, cyclization, and Dimroth rearrangement. The instability of 7a (X=I) in aqueous alkali was compared with that of the four possible N^x, 9-dimethyl isomers, and the relative ease with which the adenine ring underwent hydrolytic ring fission was found to decrease in the order 3,9- (17)>7,9- (18)>1,9- (19)>3,7- (7a)≫N^6,9-dimethyl isomer (20).
- 公益社団法人日本薬学会の論文
- 1988-01-25
著者
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斎藤 徹
Faculty Of Pharmaceutical Sciences Kanazawa University
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井上 勲
Faculty Of Pharmaceutical Sciences Kanazawa University
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藤井 澄三
Faculty Of Pharmaceutical Sciences Kanazawa University
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田村 克巳
Third Institute Of New Drug Research Otsuka Pharmaceutical Co. Ltd.
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熊澤 幸成
Faculty of Pharmaceutical Sciences, Kanazawa University
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田村 克巳
Faculty of Pharmaceutical Sciences, Kanazawa University
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Tamura K
Third Institute Of New Drug Research Otsuka Pharmaceutical Co. Ltd.
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藤井 澄三
Shinshu Univ. Nagano Jpn
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熊澤 幸成
Faculty Of Pharmaceutical Sciences Kanazawa University
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