Chemical and Pharmaceutical Bulletin p. 2318 - 2321 (1996)
Update date:2022-08-25
Topics:
Itaya, Taisuke
Takada, Yasutaka
Kanai, Tae
Fujii, Tozo
On treatment with boiling 2N hydrochloric acid for 48h, N6-methyl-8- oxoadenosine (1), 1-methyl-8-oxnadenosine (5), and 7-methyl-8-oxoadenosine (8) underwent glycosidic hydrolysis, though much more slowly than the corresponding 8-unsubstituted compounds, furnishing the aglycons (2, 6, and 9) in 45%-63% yields. Under these conditions, N6-methyl-8-oxoadenine (2) rearranged to 9-methyl-8-oxoadenine (3) (8% yield), presumably through fission and reclosure of the imidazole ring. Apparent methyl migration also occurred with 3-methyl-8-hydroxyadenine (7), which afforded 1-methyl-8- oxoadenine (6) in 9% yield on treatment with hydrochloric acid under similar conditions.
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