Purines. XXXVII. : Synthesis and Reduction of 3,9-Diallkyladenine Salts Deuterated at the 2-Position : Their Use in the Proton Nuclear Magnetic Resonance Study of Isotopically Unmodified Species
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概要
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The 2-deuterated species XI-XIII of 3,9-dimethyladenine salts (Ia, b) and of 3-benzyl-9-methyladenine perchlorate (Ie) have been synthesized from the alkylaminoimidazoles VII and VIII through deuterioformylation with formic-d acid-d, hydrogenolytic demethoxylation, adn amidine-formamido cyclization. Comparison of the proton nuclear magnetic resonance spectra of XI-XIII with those of the isotophically unmodified species Ia, b, e permitted a distinction between C(2)-and C(8)-proton signals observed for a series of 3,9-dialkyladenine salts (Ia-I) : the C(2)-proton resonates at lower field than does the C(8)-proton by 0.04-0.52 ppm. The low electron density at C(2) of I was also exemplified by the NaBH_4 reduction of 3,9-dimethyladenine perchlorate (Ib) to give the 1,2-dihydro derivatibe XIX. The structrue of XIX was confirmed by a similar reduction of the 2-deuterated species XII, leading to XX.
- 公益社団法人日本薬学会の論文
- 1990-01-25
著者
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斎藤 徹
Faculty Of Pharmaceutical Sciences Kanazawa University
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藤井 澄三
Faculty Of Pharmaceutical Sciences Kanazawa University
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木津 京子
Faculty of Pharmaceutical Sciences, Kanazawa University
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木津 京子
Faculty Of Pharmaceutical Sciences Kanazawa University
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中坂 剛志
Faculty of Pharmaceutical Sciences, Kanazawa University
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藤井 澄三
Shinshu Univ. Nagano Jpn
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中坂 剛志
Faculty Of Pharmaceutical Sciences Kanazawa University
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