Synthesis of 1,2,4-triazole C-nucleosides from hydrazonyl chlorides and nitriles |
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Authors: | Al-Masoudi Najim A Al-Soud Yaseen A Ali Ibrahim A I |
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Institution: | Formerly Fachbereich Chemie, Universit?t Konstanz, Konstanz, Germany. Najim.Al-Masoudi@gmx.de |
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Abstract: | 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 bisalpha-(4-methoxyphenyl)aminobenzylidene]-hydrazine with peracylated 1-amino-D-manno-pentitol. |
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