Reactivity of N-benzyl-3-nitrophthalimide: A facile access to isoindolo [1,2-d][3,5]benzothiazocine derivatives

A functionalized isoindolo[1,2-d][3,5]benzothiazocine 2B has been synthesiz ed in three steps from the nitro-imide derivative 5, The key step of this s equence was the cyclization of the thioglycolic acid derivative 9 under aci dic conditions. An evaluation of the reactivity of the imide 5 and the corr esponding N-acyliminium ion toward borohydride reduction, organometallic ad dition, Meyer-Schuster rearrangement and intermolecular alkoxylation and th ioalkoxylation reactions was reported.