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Paper | Regular issue | Vol 31, No. 12, 1990, pp.2225-2230
Published online, 1st January, 1970
DOI: 10.3987/COM-90-5615
C-Nucleosides. 15. Novel Ring Transformation of 6-Hydroxy-6-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2,6-dihydropyran-3-one with Amidines to Imidazole

Isamu Maeba,* Kazuya Osaka, and Chihiro Ito

*Faculty of Pharmacy, Meijo University, 150 Yagotoyama, Tempaku, Nagoya 468-8503, Japan

Abstract

The novel ring transformation of 6-hydroxy-6-(2,3,5-tir-O-benzoyl-β-D-ribofuranoxyl)-2,6-dihydropyran-3-one (1) with amidines to imidazole is described. Treatment of 1 with benzamidine afforded 3-[2-phenyl-4-(2,3,5-tri-O-benzoyl-β-D-ribofuranoxyl)imidazolyl]-2-oxo-1-propanol (2) in 53% yield. Treatment of 1 with O-methylisourea afforded 2-methoxyimidazole (3) in 27% yield. Treatment of 1 with acetamidine afforded 2-methylimidazole (4) in 10% yield. However, debenzoylation of 3 and 4 with alkaline did not afforded the deprotected imidazole C-nucleosides.