The o-quinone monoimide (7) undergoes inverse electron demand Diels-Alder reactions with 1-benzenesulfonyl- and 1-carbomethoxypyrroles. The initial adduct (9), formed when 7 interacts with 1-carbomethoxypyrrole, underwent a further cycloaddition with 7 yielding a 2:1 adduct (10). Similar 2:1 adducts result when 7 reacts with 1-methyl-2-acetyl- and 1-methyl-2-carbomethoxypyrroles. Compound (7) reacts formally as an electrophile when it is admired with 1-methyl- and 1-methyl-3-acetylpyrroles to give substituted pyrroles.