Purines. LXIV syntheses of 9-methyl-2-azaadenine 1-oxide, its O-methyl derivative, and 1-substituted 5-azidoimidazole-4-carboxamides

Article abstract of DOI:10.1248/cpb.42.2263

Diazotization of 5-amino-N'-methoxy-1-methylimidazole-4-carboxamidine (4a) with NaNO₂, in 1 N aqueous HCl was found to give the 1-methoxy-2-azaadenine derivative 8a · HI, which produced 5-azido-1-methylimidazole-4-carbonitrile (5a) on treatment with aqueous Na₂CO₃. The ribosyl analogue 5b, obtained from the riboside 4b by similar diazotization, was utilized for the synthesis of 5-azido-1-β-D-ribofuranosylimidazole-4-carboxamide (9b), a novel AICA riboside analogue. On heating in HCONMe₂ at 700C for 10 min, 8a · HI yielded the 1-N-oxide 7a. Several reactions to transform the functional groups in 5a were also investigated.

Full text of DOI:10.1248/cpb.42.2263

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