Synthesis and characterization of new substituted adenines

ABSTRACT

The reaction of the 5-aminoimidazole-4-carbonitrile 3 with hydroxylamine hydrochloride, followed by cyclization with triethyl orthoformate gave the 6-aminopurine-l-oxide-derivative 5. Quarternization of 5 with alkyl iodides afforded the unexpected purinium iodide salts 7, which were obtained also from reacting the 6-aminopurine 6 with the same alkyl iodides. Treatment of 7 with alkali gave the rearranged products 9. The triazolopurines 15 and 16 were synthesized from the 6-hydrazinopurine 13 and 1-amino-6 iminopurine 12, respectively. Rearrangement of 15 to the triazole 16 was also carried out. The 3-[5-amino-1-[p-chlorophenyl] imidazol-4-yl]-1,2,4-triazole 17 was obtained from treating 16 with alkali. The imidazotriazolo-triazine 18 and substituted triazoles 19 and 20 were afforded from reacting 17 with nitrous acid and dimethyl sulfate, respectively. The reaction of 3 with methyl-, ethyl- and phenyl-isothiocyanates gave the imidazothiazine derivatives 22. Whereas, when the reaction was carried out with n-butyl- isothiocyanate, the 6-[-n-butyl] amino-2-[n-butyl] dithiocarbamylpurine 23 was obtained