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Communication | Regular issue | Vol 38, No. 2, 1994, pp.253-258
Published online, 1st January, 1970
DOI: 10.3987/COM-93-6574
■ Synthesis of the N(1)- and N(3)-Oxides of 7-Benzyladenine

Kazuo Ogawa, Tohru Saito, Taisuke Itaya, and Tozo Fujii*

*Faculty of Pharmaceutical Scicences, Kanazawa University, 13-1 Takara-machi, Kanazawa 920-0934, Japan

Abstract

Oxidation of 7-benzyladenine (9) with m-chloroperoxybenzoic acid in MeOH has been found to yield 7-benzyladenine 1-oxide (11) as the main product. Alternatively, the same N-oxide (11) has been synthesized in 81% yield from 1-benzyl-4-(ethoxymethyleneamino)imidazole-5-carbonitrile (12) and hydroxylamine. Treatment of 1-benzyl-4-(hydroxyamino)imidazole-5-carbonitrile (17), prepared in 63% yield from the corresponding 4-nitro derivative (13) by catalytic reduction (Pt/H2), with formamidine acetate in boiling EtOH gave 7-beznyladenine 3-oxide (16) in 83% yield.