CH Arylation using acyl thiourea ligands: Applications in the synthesis of 3,6-diaryl-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles

Synthesis of a series of new 3,6-diaryl-[1,2,4]triazolo[3,4-b] [1,3,4]thiadiazoles (5a–o) was achieved by phophine free, CH arylative cross-coupling of 6-aryl-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles (4a–o) with suitably substituted iodoanilines using 1-(2-naphthoyl)-3-(4-bromophenyl)thiourea as a ligand. The requisite triazolothiadiazoles (4a–o) were obtained by the condensation of 4-amino-1,2,4-triazole-3-thiol (3) with suitably substituted aromatic acids in the presence of phosphoryl chloride.

Graphical abstractNew 3,6-diaryl-[1,2,4]triazolo[3,4-b] [1,3,4]thiadiazoles were obtained by phophine free, CH arylative cross-coupling of 6-aryl-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles with suitably substituted iodoanilines using 1-(2-naphthoyl)-3-(4-bromophenyl)thiourea as a ligand.Figure optionsDownload full-size imageDownload as PowerPoint slide