Purines. LXXII. Oxidation of N^6-Alkyladenines with m-Chloroperoxybenzoic Acid Leading to N^6-Alkyladenine 1-Oxides

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概要

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• Oxidations of N^6-methyladenine (8a) and N^6-benzyladenine (8b) with m-chloroperoxybenzoic acid (MCPBA) in methanol have been found to afford the N(1)-oxides 7a, b in 36% and 35% yields, respectively. The structure of 7b has been established by leading it to N^6-methoxyadenine (10) through O-methylation, Dimroth rearrangement, and nonreductive debenzylation. On the other hand, N^6,N^6-dimethyladenine (16) afforded the N(3)-oxide 17 in 40% yield on treatment with MCPBA in methanol. On the basis of these findings, together with data accumulated for N-oxidations of adenine, N^x-monosubstituted adenines, and 6-substituted purines, the formation of hydrogen bonding between the 6-amino NH and the carbonyl oxygen of a peroxycarboxylic acid may account for regioselective N(1)- and N(7)-oxidations of adenine and N^x-monosubstituted adenines.

• 公益社団法人日本薬学会の論文
• 1996-05-15

著者

• 藤井 澄三

  金沢大学薬学部

• Itaya T

  Faculty Of Pharmaceutical Sciences Kanazawa University

• ITAYA Taisuke

  Faculty of Pharmaceutical Sciences, Kanazawa University

• Itaya Taisuke

  Faculty Of Pharmaceutical Sciences Kanazawa University

• TAKADA Yasutaka

  Faculty of Pharmaceutical Sciences, Kanazawa University

• FUJII Tozo

  Faculty of Pharmaceutical Sciences, Kanazawa University

• OGAWA Kazuo

  Faculty of Pharmaceutical Sciences, Kanazawa University

• Fujii Tozo

  Faculty Of Pharmaceutical Sciences Kanazawa University

• Takada Y

  Rikkyo Univ. Tokyo Jpn

• Takada Yasutaka

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 藤井 澄三

  Shinshu Univ. Nagano Jpn

• Ogawa Kazuo

  Faculty Of Pharmaceutical Sciences Kanazawa University

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