The synthesis of trifunctional isomeric benzothiazoles derived from nitroanthranilic acids and their corresponding anthranilonitrile analogues is studied. Compared to previous work, the reaction sequence affords convenient access to hitherto undescribed 2-cyanobenzothiazoles. For further synthetic applications of these polyfunctional compounds, a hydrolysis–decarboxylation sequence is performed in an acidic medium (HCl or HBr), leading to an enlarged array of relevant building blocks.