Isoindole-1,3-dione amine

The condensation of 2,5-disubstituted pyrroles or 1,2,5-trisubstituted pyrroles with 1,4-diones under acidic conditions generates the isoindole system. This is a convenient route (i.e., with 2,5-disubstituted pyrroles) to JV-unsubstituted (and therefore potentially tautomeric) compounds.5 76-78 Certain isoindoles can be obtained directly from the 1,4-dione and ammonia or primary amine under acidic conditions77 or by the self-condensation of 2,5-disubstituted pyrroles under acidic conditions78 (Scheme 8). The pyrrole self-condensation may be rationalized as shown in Eq. (13) the other reactions are mechanistically analogous. 

C-Amination. TSH may also serve as a source of nucleophilic nitrogen. Thus, tetrahydrophthalic anhydride reacted with TSH to give 2-(p-tolyloxy)-hexahydro-isoindole-l,3-dione (eq 5). ... 

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