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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 alkoxylation and thioalkoxylation reactions was reported.

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Fused isoindolo[1,3]benzo(or thieno)oxazepines 8a,b and one of their positional isomers aromatic tricyclic N,O‐acetals 13b are reported to occur efficiently in a three‐step sequence from N‐hydroxy‐methylphthalimide (6). The key step of this methodology is the intramolecular arylation of an endocyclic and/or exocyclic N‐acyliminium cation. The mechanism leading to these species, in particular to a tricyclic lactam 13b, is discussed.

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