Synthesis of Cyclic and Acyclic Pyrimidine Nucleosides Analogues with Anticipated Antiviral Activity

A convenient method for preparation of cyclic and acyclic nucleosides was achieved by alkylation of 6-(2,4-dichlorophenoxymethyl)pyrimidine-2,4-dione ( 1 ) with a variety of acyclic and cyclic activated sugar analogues, namely (2-acetoxyethoxy)methyl acetate ( 3 ), 2-(acetoxymethoxy)propane-1,3-diyl dibenzoate ( 4 ), benzyloxymethyl acetate ( 5 ), 2-acetoxy-5-(benzoyloxymethyl)tetrahydrofuran-3,4-diyl dibenzoate ( 12 ), 5-chloro-2-((4-chlorobenzoyloxy)methyl)tetrahydrofuran-3-yl 4-chlorobenzoate ( 13 ) and 2-(acetoxymethyl)-6-bromotetrahydro-2 H -pyran-3,4,5-triyl triacetate ( 14 ), respectively. Deprotection of the synthesized nucleosides was achieved by using methanolic ammonia. The structures of the newly synthesized nucleoside analogues were fully characterized by analytical methods (mass spectrometry, 1 H NMR, 13 C NMR, and elemental analysis).