Synthesis of 5-ethynyl-1-beta-D-ribofuranosyl-1H-[1,2,3]triazole-4-carboxylic acid amide (isosteric to EICAR) and its derivatives.
The synthesis of 5-ethynyl-1H-[1,2,3]triazole-4-carboxylic acid amide riboside 1 and its derivatives exploits Pd(0)-catalyzed cross-coupling reactions. The iodinated key intermediate 3a, when coupled with alkynes affords 5-alkynylated products 1b,c,e,f in diverse yields. Methanolysis of 1b and 1c provides the title compound 1 and the 5-propynyl derivative 1d, respectively. When coupled with methyl acrylate, 3a gives the E-isomer 4c, although in low yield, while the other 5-iodo precursor 3b undergoes reduction to 4b.
Ostrowski
Tomasz
T
Institute of Bioorganic Chemistry, Polish Academy of Sciences, PL-61704 Poznan, Poland.
Zeidler
Joanna
J
D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D012263:Ribonucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry
D009705:Nucleosides; D012263:Ribonucleosides; D014230:Triazoles