Synthesis of the N(1)- and N(3)-Oxides of 7-Benzyladenine

Abstract

Oxidation of 7-benzyladenine (9) with m-chloroperoxy-benzoic 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)imida- zole-5-carbonitrile (17), prepared in 63% yield from the corresponding 4-nitro derivative (13) by catalytic reduction (Pt/H 2 ), with formamidine acetate in boiling EtOH gave 7-benzyladenine 3-oxide (16) in 83% yield