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.
Al-Masoudi
Najim A
NA
Formerly Fachbereich Chemie, Universität Konstanz, Konstanz, Germany. Najim.Al-Masoudi@gmx.de
Al-Soud
Yaseen A
YA
Ali
Ibrahim A I
IA
D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry*; D002712:Chlorides / Q000737:chemistry; D006835:Hydrazones / Q000737:chemistry; D008698:Mesylates / Q000737:chemistry; D009570:Nitriles / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry; D012263:Ribonucleosides / Q000138:chemical synthesis / Q000737:chemistry*; D012835:Silver Nitrate / Q000737:chemistry; D014230:Triazoles / Q000138:chemical synthesis / Q000737:chemistry*
D000998:Antiviral Agents; D002712:Chlorides; D006835:Hydrazones; D008698:Mesylates; D009570:Nitriles; D009942:Organometallic Compounds; D012263:Ribonucleosides; D014230:Triazoles; C518808:ytterbium(III) triflate; D012835:Silver Nitrate