133535-95-2Relevant academic research and scientific papers
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
Maeba, Isamu,Osaka, Kazuya,Ito, Chihiro
, p. 2225 - 2230 (2007/10/02)
The novel ring transformation of 6-hydroxy-6-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-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-ribofuranosyl)imidazolyl]-2-oxo-1-propanol (2) in 53% yield. 1H and 13C nmr spectra of 2 accounted for the contribution of tautomeric structure. Deprotection of 2 with methanolic sodium hydroxide afforded 3-[2-phenyl-4-(β-D-ribofuranosyl)imidazolyl]-2-oxo-1-propanol (5) in 35% 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.
