Nucleosides 5(15): synthesis of novel 1,2,4-triazolo[3,4-c]-1,2,4-triazole nucleosides

Nucleosides Nucleotides Nucleic Acids. 2009 Nov;28(11):1095-103. doi: 10.1080/15257770903368377.

Abstract

Ribosylation of 3-methylthio-5-phenyl-1,2,4-triazole (1) with ribose derivative 2 gave the protected 1,2,4-triazole-nucleoside 3, which reacted with hydrazine hydrate to afford the 3-hydrazino-1,2,4-triazole derivative 5. Reaction of 5 with aromatic aldehydes yielded the corresponding hydrazones 6, which cyclized under bromination in acetic acid to give 8. Debenzoylation of 8 afforded novel 1,2,4-triazolo[3,4-c]-1,2,4-triazole nucleosides 9.

MeSH terms

  • Acetic Acid / chemistry
  • Bromine / chemistry
  • Cyclization
  • Hydrazones / chemistry
  • Molecular Structure
  • Nucleosides / chemical synthesis*
  • Nucleosides / chemistry
  • Triazoles / chemical synthesis*
  • Triazoles / chemistry

Substances

  • Hydrazones
  • Nucleosides
  • Triazoles
  • 1,2,4-triazole
  • Acetic Acid
  • Bromine