An anomalous preparing of a tetrahydro-2H-oxocine fused pyrrole derivative and its acid-catalyzed rearrangement

Article abstract of DOI:10.3987/COM-98-8437

Condensation of 5-methylthio-2-benzoylpyrrole (1) with spiro[2.5]-5,7- dioxa-6,6-dimethyloctane-4,8-dione (3) using excess mount of Nail in DMF gave an anomalous tetrahydro-2H-oxocine fused pyrrole (10), which then undergoes an acid-catalyzed rearrangement in refluxing toluene/methanol (10:1, v/v) to afford the unexpected anti-aromatic compounds (15 and 16).