Synthesis of N ²-Arylisocytidines and N ²-Aryl-2′-deoxyisocytidines

Summary.

2-(Arylamino)pyrimidin-4-ones were synthesized, silylated, and condensed with l,2,3,5-tetra-O-acetyl-β- d-ribofuranoside to afford the corresponding N ²-aryl protected isocytidines. Deprotection of the acetylated isocytidines using saturated NH₃ in MeOH solution gave 1-(β-d-ribofuranosyl)-2-(arylamino)-4-pyrimidinones. Methyl 2-deoxy-3,5-di-O-toluyl-α/β-d-ribofuranoside was prepared and condensed with the previously silylated bases to afford the anomeric mixture of protected nucleosides. The pure β-anomers were synthesized with better yield by treating the sodium salts of N ²-arylisocytosine derivatives with 2-deoxy-3,5-di-O-toluyl-α-d-ribofuranosyl chloride. Deprotection of the latter anomers afforded the corresponding free hydroxyl derivatives. The synthesized free nucleosides are under antiviral and oligonucleotide investigations.