Purines. LXIX. Direct N(1)-Oxidation of 7-Benzyladenine and Stepwise Syntheses of Its N(1)- and N(3)-Oxides
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概要
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In contrast to the N(3)-selectivity in N-alkylation, N-oxidation of 7-benzyladenine (17) with m-chloroperoxybenzoic acid in MeOH has been found to give 7-benzyladenine 1-oxide (18) in 76% yield. Alternatively, the same N-oxide (18) has been synthesized in 81% yield from 1-benzyl-4-(ethoxymethyleneamino)imidazole-5-carbonitrile(19) and hydroxylamine. Treatment of 1-benzyl-4-(hydroxyamino)imidazole-5-carbonitrile (24), obtained in 63% yield from the corresponding 4-nitro drivative (20) by catalytic hydrogenation (Pt/H_2), with formamidine acetate in boiling EtOH furnished 7-benzyladenine 3-oxyde (23) in 78% yield. A UV spectroscopic approach indicated that the neutral species of 18 exists in H_2O in the N(1)-oxide form rather than the N(1)-OH form (27).
- 社団法人日本薬学会の論文
- 1995-02-15
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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藤井 澄三
金沢大学薬学部
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小川 和男
Faculty Of Pharmaceutical Sciences Kanazawa University
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板谷 泰助
Faculty of Pharmaceutical Sciences, Kanazawa University
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板谷 泰助
金沢大学薬学部
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Saito T
Research And Development Headquarters Hokurikit Seiyaku Co. Ltd.
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Ogawa K
Showa Pharmaceutical University
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藤井 澄三
Shinshu Univ. Nagano Jpn
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