Spiro-heterocyclization of 1H-pyrrole-2,3-dione at the treatment with 3-arylamino-1H-inden-1-ones

Three-component spiro heterocyclization of 1H-pyrrole-2,3-dione by the action of 3-arylamino-1H-inden-1-ones

“…line-10,3′-pyrroles] [3], gave minor ethyl 5-aryl-2′,10,12-trioxo-1′,5′-diphenyl-1′,2′,10,12-tetrahydro-5H-spiro[diindeno [1,2-b : 2′,1′-e]pyridine-11,3′-pyrrole]-4′-carboxylates IIIa and IIIb whose structure was confirmed by X-ray analysis of compound IIIa.…”

“…We previously reported on spiro heterocyclization of substituted 1H-pyrrole-2,3-diones by the action of N-aryl-substituted carbocyclic enamines (3-arylaminocyclohex-2-en-1-ones and 3-arylamino-1H-inden-1-ones) with formation of spiro[acridine-9,3′-pyrroles] [1, 2] and spiro[indeno[1,2-b]quinoline-10,3′-pyrroles], respectively [3].…”

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SHORT COMMUNICATIONSWe previously reported on spiro heterocyclization of substituted 1H-pyrrole-2,3-diones by the action of N-aryl-substituted carbocyclic enamines (3-arylaminocyclohex-2-en-1-ones and 3-arylamino-1H-inden-1-ones) with formation of spiro[acridine-9,3′-pyrroles] [1, 2] and spiro[indeno[1,2-b]quinoline-10,3′-pyrroles], respectively [3].The reaction of ethyl 1,2-diphenyl-4,5-dioxo-1H-pyrrole-3-carboxylate (I) with 3-arylamino-1H-inden-1-ones IIa and IIb at a molar ratio of 1 : 1 in anhydrous m-xylene at 139-140°C for 5-6 h, apart from the expected products, substituted spiro[indeno[1,2-b]quinoline-10,3′-pyrroles] [3], gave minor ethyl 5-aryl-2′,10,12-trioxo-1′,5′-diphenyl-1′,2′,10,12-tetrahydro-5H-spiro[diindeno[1,2-b : 2′,1′-e]pyridine-11,3′-pyrrole]-4′-carboxylates IIIa and IIIb whose structure was confirmed by X-ray analysis of compound IIIa.Presumably, compounds IIIa and IIIb are formed via initial condensation of pyrroledione I at the ketone carbonyl group with 3-arylamino-1H-inden-1-one II with formation of intermediate indan-2-ylidene derivative A, nucleophilic addition of the C 2 carbon atom in II at the C 4 carbon atom in the pyrrole ring of A, and subsequent intramolecular ring closure as a result of Ar = Ph (a), 4-MeC 6 H 4 (b).

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Organocatalytic asymmetric Henry reaction of 1H-pyrrole-2,3-diones with bifunctional amine-thiourea catalysts bearing multiple hydrogen-bond donors

“…The reaction of 1 H -pyrrole-2,3-diones with various nucleophiles should be a straightforward way to access diverse and interesting 3-substituted-3-hydroxy-1 H -pyrrol-2(3 H )-ones. A survey of the literature reveals that the study of 1 H -pyrrole-2,3-diones is mainly focused on three-component spiro-heterocyclization reactions [30–32]. However, for the catalytic asymmetric transformation, only one example of an aldol reaction of 1 H -pyrrole-2,3-diones with ketones has been reported so far (Scheme 1) [33].…”

Direct spiro heterocyclization of methyl 3-aroyl-1-aryl-4,5-dioxo-4,5-dihydro-1H-pyrrole-5-carboxylate by the action of 3-amino-1H-inden-1-one

“…We previously described spiro heterocyclization of 1-substituted ethyl 4,5-dioxo-2-phenyl-1H-pyrrole-3-carboxylates with 3-arylamino-1H-inden-1-ones at ratios of 1 : 1 and 1 : 2, which led to the formation of spiro[indeno [1,2-b]quinoline-10,3′-pyrrole] [1] and spiro[diindeno[1,2-b:2′,1′-e]pyridine-11,3′-pyrrole] derivatives [2], respectively. In both cases, the reactions involved the 4-C=O group of the initial dioxopyrrole.…”