synthesis of some cyclic and acyclic nucleosides

4-( 4-Chlorophenyl)-2-(2’,3’,4’ ,6’ -tetra-O-acetyl-fJ-D-glucol galactopyra­nosyloxy)-6-(thien-2-yl)nicotinonitrile (5 and 9), xyloside 13 riboside 16,and lactoside 19 were prepared by the reaction of pyridin-2(1H)-one 2with glycosyl I galactosyl I xylosyl I lactosyl bromide and peracetylatedxylose I ribose under the conventional and microwave irradiationmethods. The glycosides 5, 9, 13, 16 and 19 were deacetylated in thepresence ofEt3NIMeOH and few DROPs of water to give 6, 10, 14, 17 and20. Then the reaction of 2 with 4-bromobutylacetate (23), (2-acetoxyethoxy)methyl bromide (24) gave the correspondingnicotinonitrile O-acyclonucleosides, 25 and 27, respectively. Whichdeacetylated to give the corresponding deprotected acyclonucleosides 26and 28, respectively. Treatment of 2 with 1,3-dichloropropan-2-01 (29),epichlorohydrin (31) and allyl bromide (33) gave the correspondingnicotinonitrile O-acyclonucleosides 30, 32 and 34, respectively.Futhermore, Reaction of 2 with the propargyl bromide (35) gave thecorresponding 2-0-propargyl derivative 36, which was reacted via [3+2]cycloaddition with 4-azidobutyl acetate (37) and [(2-acetoxyethoxy)methyl]azide (38) to give the corresponding 1,2,3-triazolederivatives 39 and 40, respectively. Selected members of thesecompounds were screened for antitumor and antibacterial activity.