Synthesis of 2-aminobenzo[b]thiophenes from 4-(2-haloaryl)-1,2,3-thiadiazoles

Copper(I) iodide-catalyzed synthesis of 1-benzothiophen-2-amines from 4-(2-bromophenyl)-1,2,3-thiadiazole

“…The subsequent acidification led to the formation of 2-(2-halophenyl)thioacetic acid morpholides. However, introduction of a nitro group into the para position with respect to the chlorine atom in 4-(2-chlorophenyl)-1,2,3-thiadiazole resulted in successful synthesis of 2-dialkylamino-1benzothiophenes [10].…”

“…Herein we describe a new method for the preparation of 2-amino-1-benzothiophenes from 4-(2-bromophenyl)-1,2,3-thiadiazole (1) [10] and secondary amines (morpholine and piperidine) in the presence of potassium carbonate and a catalytic amount of copper R 2 N = morpholin-4-yl (a), piperidin-1-yl (b). The structure of 5a and 5b was confirmed by the 1 H and 13 C NMR and mass spectra, as well as by comparison with published data [6,7].…”