Methyl 1-aryl-3-benzoyl-4,5-dioxo-4,5-dihydro-1H-pyrrole-2-carboxylates reacted with 6-amino-1,3-dimethylpyrimidine-2,4(1H,3H)-dione to give methyl 11-aryl-12-benzoyl-9-hydroxy-4,6-dimethyl-3,5,10-trioxo-4,6,8,11-tetraazatricyclo[7.2.1.0 2,7 ]dodec-2(7)-ene-1-carboxylates which underwent thermal recyclization to 1-aryl-3-benzoyl-4-hydroxy-Monocyclic 1H-pyrrole-2,3-diones are known to react with difunctional nucleophiles to produce various five-, six-, and seven-membered nitrogen-containing heterocycles, as well as fused and spirocyclic systems [2,3]. We previously showed that methyl 1-aryl-3-aroyl-4,5-dioxo-4,5-dihydro-1H-pyrrole-2-carboxylates react with 3-amino-5,5-dimethylcyclohex-2-en-1-one (as 1,3-C,N-binucleophile) via successive addition of the β-CH group and amino group in the enamino fragment of the binucleophile at the carbon atoms in positions 2 and 4 of dioxopyrrole with formation of diazatricyclo[7.2.1.0 2,7 ]dodec-2(7)-ene derivatives. The latter undergo recyclization on heating to give spiro[indole-3,2′-pyrroles] together with spiro-[furan-2,3′-indoles] as by-products [4,5]. Reactions of methyl 1-aryl-3-aroyl-4,5-dioxo-4,5-dihydro-1H-pyrrole-2-carboxylates with heterocyclic enamines were not studied.