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Nadirova, Maryana А.; Pokazeev, Kuz’ma M.; Kolesnik, Irina А.; Dorovatovskii, Pavel V.; Bumagin, Nikolay А.; Potkin, Vladimir I.
Chemistry of heterocyclic compounds (New York, N.Y. 1965), 08/2019, Letnik: 55, Številka: 8Journal Article
It was found that the reaction of 5-arylfurfurilamines with maleic anhydride leads to the formation of 6-aryl-3a,6-epoxyisoindole-7-carboxylic acids (the cyclic form), which in solution are in dynamic equilibrium with N -furfurylmaleinamides (the open form). During the esterification of these tautomeric mixtures with methanol in the presence of a catalytic amount of sulfuric acid, methyl esters of 5-aryl-7a-hydroxy-7-methoxy-3-oxo-2,3,3a,4,7,7a-hexahydro-1 H -isoindole-4-carboxylic acids, unexpected cleavage products of the 3a,6-oxo bridge of the cyclic form, are formed diastereospecifically. The structure of the obtained products was confirmed by X-ray structural analysis.
