Nitro derivatives of 2,1,3-benzothiadiazole 1-oxides: synthesis, structural study, and NO release

A convenient one-pot synthesis of nitro derivatives of 2,1,3-benzothiadiazole 1-oxides by the reaction of o-nitroanilines with sulfur monochloride was developed. The structural features of 4-nitrobenzothiadiazole and its N-oxide were considered. High in vitro release of nitric oxide (69%) was found for a 6-nitro-2,1,3-benzothiadiazole sample by the Griess assay, which indicated good prospects for this class of compounds.