In the present work, we developed robust processes for the preparation of new antitrypanosomal benzofuroxans, E and Z isomers of 5-arylethenylbenzo [1, 2-c] 1, 2, 5- oxadiazole N 1-oxide 1–6, in multigram batch through Wittig− Boden conditions as the key synthetic step. In these conditions, the generation of the benzofurazans, as secondary byproduct, was minimized.