Abstract A functionalized isoindolo [1, 2-d][3, 5] benzothiazocine 2B has been synthesized in three steps from the nitro-imide derivative 5. The key step of this sequence was the cyclization of the thioglycolic acid derivative 9 under acidic conditions. An evaluation of the reactivity of the imide 5 and the corresponding N-acyliminium ion toward borohydride reduction, organometallic addition, Meyer-Schuster rearrangement and intermolecular ...