New route of reaction of 4-acyl-1H-pyrrole-2,3-diones with 1,3-CH,NH-binucleophile

Reactions are described of 1-aryl-4-aroyl-5methoxycarbonyl-1Н -pyrrole-2,3-diones with acyclic [1], carbocyclic [2] and heterocyclic [3] 1,3-СН,NH-binucleophiles leading to the formation of spirobisheterocyclic or bridging heterocyclic systems due to the involvement of pyrrolediones in these reactions by atom С5 and methoxycarbonyl group or atom С3 respectively. At boiling substituted 5-methoxycarbonyl-1-(4-tolyl)1Н-pyrrole-2,3-diones Iа, Ib and 5-amino-3-methyl-1phenyl-1Н-pyrazole (II) in 1:1 ratio in anhydrous benzene for 1–1.5 h (TLC monitoring) we obtained methyl 6-R-3methyl-5-[2-oxo-2-(4-tolylamino)acetyl]-1-phenyl-1Hpyrazolo[3,4-b]pyridine-4-carboxylates IIIа, IIIb. The formation of compounds IIIа, IIIb occurs apparently through primary addition of the β-СН group of the enamino fragment of compound II to the atom С5 of pyrrolediones Ia, Ib followed by the intramolecular reaction of the primary amino group with the carbonyl group of the acyl substituent in the position 4 and by the opening of the pyrrole ring at the N1–C5 bond. The described reaction is an example of the new route of the reaction between 1-aryl-4-acyl-5-methoxycarbonyl1Н-pyrrole-2,3-diones and 1,3-СН,NH-binucleophiles,