Carbocyclic analogs of thymine nucleosides and related 1-substituted thymines

The carbocyclic analogs of thymidine (IXf), 1-β-ribofuranosylthymine (IXg), and 1-β-3′-deoxyribofuranosyl-thymine (IXe) were synthesized by incorporating modifications into the Shaw method of synthesizing 2,4-(1H,3H)pyrimidinediones via acryloylureas. Simpler analogs of thymine nucleosides were also prepared by this method. The carbocyclic analog of thymidine displayed modest activity against Leukemia L1210 in vivo. It differs from a compound prepared previously by a Prins reaction.