Synthesis of fluorinated imidazolopyridines from pentafluoropyridine

Heteroaromatic systems have, of course, vast chemistry.1 Perhalogenated heteroaromatic systems are an essential class of heterocyclic compounds with potentially various use in organic chemistry, biochemistry, and pharmaceutical chemistry. Many researchers are concerned about the reactions of different N, O, S, C, and P nucleophiles with perhalogenated compounds. The order of nucleophilic attack on pentafluoropyridine follows the sequence 4-F > 2-F > 3-F. Due to their high electronegativity, fluorine atoms are able to modify the physicochemical attributes of molecules drastically.2-3 We report the synthesis of new 1-(4, 6, 7-trifluoro-2-thioxo-2, 3-dihydro-1H-imidazo [4, 5-c] pyridin-1-yl) ethanone 3 from the reaction between pentafluoropyridine 1 and N-carbamothioylacetamide 2 after heating together at reflux temperature in THF in the presence of potassium carbonate. All synthesized compounds are stable solids whose structures were determined on the basis of their 1H and 13C NMR and 19F-NMR and IR spectroscopic data.

کلیدواژه ها:

Pentafluoropyridine ، N-carbamothioylacetamide ، Synthesis