Previously we have reported on the antiinflammatory [1] and antiviral [2] properties of 1,4,5-trisubstituted tetrahydropyrrole-2,3 -diones.tn continuation of the search for biologically active compounds in the series of substituted tetrahydropyrrole-2,3-diones (structurally similar to pyracetam), it was of interest to attempt their synthesis by the method described in [2], using natural co-and 13-amino acids as the amino components, and study the nootropic, antibacterial, antiinflammatory, and analgesic activity.For this purpose we have studied the interaction of methyl ester of acetylpyruvic acid with a mixture of an aromatic aldehyde and amino acid. Our experiments showed that short-time heating of glycine (as the amino acid) in alcohol, followed by holding the reaction mixture at room temperature, leads to 5-aryl-4-acetyl-l-carboxyalkyltetrahydropyrrole-2,3-diones (I -V) with good yield.
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method in [4 + 2] cycloaddition.It is known that thermolysis of 5-aryl-2,3-dihydro-2,3-furandiones (benzene, 80°C) is accompanied by the elimination of carbon monoxide and leads to 3-aroyl-6-aryl-4-hydroxy-2H-pyran-2-ones [1]. The formation of substituted pyrans in this reaction is explained by the dimerization of aroylketenes, the primary thermolysis products. The fact of forming aroylketenes as a result of thermal decarbonylation of furandiones was reliably confirmed in [2].It was shown previously that aroylketenes generated in a similar way react with compounds containing a C=N bond and an activated C≡N bond with the formation of [4 + 2] cycloaddition products, 6-substituted 3,4-dihydro-2H-1,3-oxazin-4-ones [3][4][5] or 4H-1,3-oxazin-4-ones [6-8] respectively. Many of the 1,3-oxazines obtained in this way display biological activity [9], which makes it expedient to study these reactions further.In the presence of compounds with an unactivated cyano group (MeCN, PhCN) aroylketenes are dimerized [7].The interaction of 5-aryl-2,3-dihydro-2,3-furandiones with compounds containing C=N and C≡N bonds simultaneously, and also activated and unactivated C≡N bonds is practically unstudied. It is known only that as a result of the reaction of 5-aryl-2,3-dihydro-2,3-furandiones with methylenaminoacetonitrile, a compound containing isolated C=N and C≡N bonds (toluene, 110°C, 1.5 h), the latter reacts as an azomethine by a [4 + 2] cycloaddition reaction with the resulting aroylketenes. In the course of this reaction 6-aryl-3-cyanomethyl-3,4-__________________________________________________________________________________________
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