ChemInform Abstract: 4‐Azido‐2‐pyrimidinone Nucleosides and Related Chemistry.

Abstract

4-Azido-2-pyrimidinone Nucleosides and Related Chemistry.-With a view to develop prodrugs for antitumor and antiviral agents, compound (IV) is synthesized and its chemical stability is studied at various pHs by UV spectroscopy. Under acidic conditions (IV) remains stable, but even at pH 7 an 2',6-anhydro bond formation is observed leading to cyclized product (V). The fluoro analogue (VI) shows another reactivity. It is stable at pH 7.4 and undergoes at higher pHs in the presence of NH 4 OH an amine addition yielding product (VII). This demonstrates, that the presence of 2'-OH in the arabino configuration in compound (IV) is necessary for the 2',6-linkage. -(KOTRA, L. P.; WANG, P.; BARTLETT, M. G.; SHANMUGANATHAN, K.; XU, Z.; CAVALCANTI, S.; NEWTON, M. G.; CHU, C. K.; J.