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Communication | Special issue | Vol 30, No. 1, 1990, pp.329-332
Published online, 1st January, 1970
DOI: 10.3987/COM-89-S56
A Unique Transformation of 5-Amino-N’-methoxyimidazole-4-carboxamidines by Diazotization: Synthesis of the 5-Azido Analogue of ACIA Riboside

Tohru Saito, Yayoi Asahi, Satoshi Nakajima, and Tozo Fujii*

*Faculty of Pharmaceutical Scicences, Kanazawa University, 13-1 Takara-machi, Kanazawa 920-0934, Japan


Diazotization of 1-substituted 5-amino-N’-methoxyimidazole-4-carboxamidines (I) was found to give the 5-azidoimidazole-4-carbonitriles II through the 1-methoxy-2-azaadenine intermediates IV. The product IIb from the riboside Ib was utilized for the synthesis of 5-azido-1-β-D-ribofuranosylimidazole-4-carboxamide (Vb), a novel AICA riboside analogue.