5444-42-8Relevant articles and documents
Synthesis and Characterization of New Substituted Adenines
Basyouni, W. M.,Hosni, Hanaa M.
, p. 251 - 268 (2007/10/03)
Reaction of the 5-aminoimidazole-4-carbonitrile 3 with hydroxylamine hydrochloride, followed by cyclization with triethyl orthoformate gave the 6-aminopurine-1-oxide derivative 5. Quaternization 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 imidazotriazolotriazine 18 and substituted triazoles 19 and 20 were afforded from reacting 17 with nitrous acid and dimethyl sulfate respectively. 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.