Synthesis of novel hydantoin, arylidene-hydantoin N-cyclic and acyclic-nucleosides

3-Monoalkyl and 1,3-dialkylhydantoin, arylidene-hydantoin derivatives were prepared by reaction of hydantoin, arylidene-hydantoin sodium salts with 1,3-dioxolan-methyllsulfate derivatives. Deprotection of the products afforded the dihydroxy and tetrahydroxy derivatives. The primary hydroxyl group was protected by reaction with DMT CI to afforded DMT protected compound, which was reacted with 2-cyanoethyl-N,N,',N'-tetraisopropylphosphordiamidite to give phosphoramidate derivative. Reaction of the 5-naphthylidene-hydantoin with 2,3,5-tri-O-benzyl-1,O-p-nitrobenzoyi-D-arabinofuranose afforded a mixture of alpha and beta ribonucleosides analogues. Removal of the protecting groups gave alpha and beta mixture of 5-naphthylidene-hydantoin ribofuranosides. On reacting the silylated 5-pyrenylidene-hydantoin with methyl-2-deoxy-3,5-di-O-p-toluoyi-D-erythro-pentafuranoside followed by deprotection furnished 5-pyrenylidene-hydantoin-alpha-D-erythro-pentafuranosyl and the corresponding beta anomer.