782393-18-4Relevant academic research and scientific papers
Ring-opening of 3-β-D-ribofuranosyl-3,7,8,9-tetrahydropyrimido [1,2-i]purin-8-ol and preparation of 2-thio- and 2-aza-adenosine derivatives
Sund, Pernilla,Kronberg, Leif
experimental part, p. 1215 - 1226 (2009/04/11)
The adduct 3-β-D-ribofuranosyl-3,7,8,9-tetrahydropyrimido[1,2-i]purin- 8-ol (2), obtained from adenosine and epichlorohydrin, underwent ring fission at basic conditions. The initial ring-opening took place at C2 of the pyrimidine unit resulting in 2-(5-amino-1-β-D-ribofuranosyl-imidazol-4-yl)-1,4,5,6- tetrahydropyrimidin-5-ol (3). Also the tetrahydropyrimidine ring of 3 could be opened resulting in 5-amino-1-(β-D-ribofuranosyl)-imidazole-4-(N-3-amino-2- hydroxyl-propyl)-carboxamide (4). In hot acid conditions, 2 was both deglycosylated and ring-opened yielding 2-(5-amino-imidazol-4-yl)-1,4,5,6- tetrahydropyrimidin-5-ol (7) as the final product. When reacting 3 with CS2 or HNO2 ring-closure took place and 3-β-D-ribofuranosyl-3,4,7,8,9- pentahydropyrimido[1,2-i]purin-8-ol-5-thione (5), and 3-β-D-ribofuranosyl- imidazo[4,5-e]-3,7,8,9-tetrahydropyrimido[1,2-c][1,2,3]triazine-8-ol (6), respectively, were obtained. Also, the pyrimidine ring of the epichlorohydrin adduct with adenine, 10-imino-5,6-dihydro-4H,10H-pyrimido[1,2,3-cd]purin-5-ol (10), underwent ring fission and the product was identified as 3-hydroxy-1,2,3,4-tetrahydroimidazo[1,5-a]pyrimidine-8-carboximidamide (11). Copyright Taylor & Francis Group, LLC.
