Abstract 5-Amino-1H-imidazole-4-carboxamide hydrochloride has been converted into a series of new, potentially biologically active N 6-substituted 2-azaadenines 5via 4-diazo-4H- imidazole-5-carbonitrile (1) which was coupled with primary amines to give 5 in 11–78% yield. Further, some 1-substituted 2-azahypoxanthines 9 have been prepared in 17–66% yield from ethyl 5-amino-1H-imidazole-4-carboxylate (6) via ethyl 4-diazo-4H-imidazole-5- ...