Pyrimidine Acyclo-C-Nucleosides by Ring Transformations of 2-Formyl-L-arabinal

Abstract

The protected 2-formyl-L-arabinal 2 reacted with thiourea and cyanamide in the presence of sodium hydride to afford via ring transformations the 5-[1R,2S-1,2- bis(benzyloxy)-3-hydroxypropyl]-1,2-dihydropyrimidines 3 and 4, respectively. Similarly, treatment of 2 with 3-amino-2H-1,2,4-triazole yielded 6-[1R,2S-1,2- bis(benzyloxy)-3-hydroxypropyl][1,2,4]-triazolo[1,5-a]pyrimidine (5).

Keywords

• Glycals
• nucleoside analogues
• pyrimidines
• fused pyrimidines
• push-pull alkenes
• ring transformation