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Synthesis of 1,2,4-triazole C-nucleosides from hydrazonyl chlorides and nitriles.

A series of 1,3-diaryl-5-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-1H-1,2,4-triazole nucleosides (3a-f) were synthesized via the intermolecular cyclization of hydrazonyl chlorides with peracylated ribofuranosyl cyanide catalyzed by Yb(OTf)3 or AgNO3, respectively. Similarly, the 1,2,4-triazole of glucopyranosyl C-nucleosides 5a,b were prepared from the hydrazonyl chlorides and the nitrile 4. Alternatively, the 1,2,4-triazole N-nucleoside 8 was obtained from cyclization of the unsymmetrical bis[alpha-(4-methoxyphenyl)aminobenzylidene]-hydrazine with peracylated 1-amino-D-manno-pentitol.[1]

References

  1. Synthesis of 1,2,4-triazole C-nucleosides from hydrazonyl chlorides and nitriles. Al-Masoudi, N.A., Al-Soud, Y.A., Ali, I.A. Nucleosides Nucleotides Nucleic Acids (2007) [Pubmed]
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