Chemical and Pharmaceutical Bulletin p. 2263 - 2268 (1994)
Update date:2022-08-03
Topics:
Saito
Asahi
Nakajima
Fujii
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.
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