New Synthesis of C- and N-Acyclic Nucleosides from 2-Hydrazinothienopyrimidone Derivatives | ||||
| Egyptian Journal of Chemistry | ||||
| Article 6, Volume 53, Issue 4, August 2010, Page 541-552 PDF (281.33 K) | ||||
| DOI: 10.21608/ejchem.2010.1248 | ||||
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| Abstract | ||||
| ACYCLIC N-nucleosides are prepared by heating under reflux 2-hydrazinocyclopentenothienopyrimidone 1 with aldopentoses in dioxane to give the corresponding acyclic N-nucleosides 2 and 3, which cyclized on stirring at room temperature in acetic anhydride/pyridine mixture to afford the corresponding protected tetra O-acetate C-nucleosides 4 and 5, respectively. De-acetylation of compound 4 and 5 afforded the free acyclic C-nucleosides 6 and 7, respectively. On the other hand, acyclic N-nucleosides 8 and 10 were obtained on treatment of 1 with aldohexoses in the same manner. The protected penta O-acetyl C-nucleosides 11-13 were obtained when stirred compounds 8-10 with acetic anhydride/pyridine mixture at room temperature. De-protection afforded the free acyclic C-nucleosides 14-16, respectively. | ||||
| Keywords | ||||
| 2-Hydrazinocyclopentenothienopyrimidone; Acyclic N- nucleosides; O-acetyl C-nucleosides and Acyclic C-nucleosides | ||||
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