A study aimed at synthesis of long-bridged pyrimidine cyclonucleosides.
Synthesis of some 2,3'-aminimino and 2,3'-N alpha, N beta-dimethylhydrazo uracil cyclonucleosides are reported as part of our recent program to expand the range of the model conformations of cyclonucleosides. 1a with monoacetate of hydrazine or of methyl-hydrazine gave 2,3'-aminimino- (3a) or 2,3'-methylaminimino-1-(5'-O-benzoyl-beta-D-lyxofuranosyl) uracil (3b) in a fair yield. 1a with diluted free bases also gave 3a,b. These were converted into the deprotected forms (4a,b). On the other hand, reaction of 1a with monoacetate of N alpha, N beta-dimethylhydrazine gave 2,3'-N alpha, N beta-dimethylhydrazo-1-beta-D-lyxofuranosyluracil (6) and its 5'-O-benzoyl derivative (5). 6 is more conveniently obtainable from the deprotected 2,2'-anhydronucleoside 7.
D055598:Chemical Phenomena; D002621:Chemistry; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis*; D014529:Uridine / Q000031:analogs & derivatives*
D011741:Pyrimidine Nucleosides; D014529:Uridine