Reaction of 5-aryl-2,3-dihydrofuran-2,3-diones with ketene acetals

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, p. 1567, November, 1991.     

Mild acylation of fischer indole with 5-aryl-2,3-dihydrofuran-2,3-diones

Russian Journal of Organic Chemistry -     

Five-membered 2,3-dioxoheterocycles. 28. Reaction of 5-aryl-2,3-dihydrofuran-2,3-diones with thioamides and thiosemicarbazides

The reaction of 5-aryl-2,3-dihydrofuran-2,3-diones (I) with thiocarbonyl compounds has been described only for thiourea. The products of this reaction are 3-aryl-5-phenacylidene-4-oxoimidazolidine-2-thiones [2]. It seemed of interest to study the conversion of the furandiones (I) with a wider range of thiocarbonyl compounds such as thioamides and thiosemicarbazides.For Communication 27 see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1461–1464, November, 1992.     

Five-membered 2,3-dioxoheterocycles 3. The reaction of 5-aryl-2,3-dihydrofuran-2,3-diones with aliphatic and aromatic nitriles

On reaction of 5-aryl-2,3-dihydrofuran-2,3-diones with -aminoisobutyronitrile, o-aminobenzonitrile, and -anilinopropiononitrile, we obtained aroylpyruvic acid N-(1-methyl-1-cyanoethyl)-, N-(o-cyanophenyl)-, and N-phenyl-N-(cyanoethyl)-amides, respectively. On reaction of 5-aryl-2,3-dihydrofuran-2,3-diones with cyanoacetamide we obtained aroylacetic acid N-(cyanoacetyl)amides, while in the case of methyleneaminoacetonitrile and p-dimethylaminobenzonitrile we obtained (6-aryl-4-oxo-2,3-dihydro-1,3-oxazin-3-yl)acetonitriles and 2-(p-dimethylaminophenyl)-6-aryl-1,3-oxazine-4-ones, respectively.For Communication 2, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 740–743, June, 1987.     

Five-membered 2,3-dioxoheterocycles. 10. Reaction of 5-aryl-2,3-dihydrofuran-2,3-diones with N-substituted ureas and their thio and seleno analogs

3-Aryl-5-phenacylideneimidazolidine-2,4-diones, 3-aryl-5-phenacylidene-4-oxoimidazolidine-2-thiones, and 5-phenacylidene-4-oxoimidazolidine-2-selenones were obtained from 5-aryl-2,3-dihydrofuran-2,3-diones and arylureas, arylthioureas, and selenoureas respectively in glacial acetic acid. In the reaction of 5-aryl-2,3-dihydrofuran-2,3-diones with cyanoguanidine in 98% acetic acid 5-phenacylideneimidazolidine-2,4-diones were isolated, and in anhydrous acetic acid 2-imino-3-amidino-5-phenacylidene-4-oxazolidones were isolated. When heated in a water-dioxane solution of hydrochloric acid, the latter are converted into 5-phenacylideneimidazolidine-2, 4-diones.For Communication 9, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1411–1413, October, 1988.     

Chemistry of acyl(imidoyl)ketenes. 7. Synthesis and thermolysis of 5-aryl-4-quinoxalinyl-2,3-dihydrofuran-2,3-diones

3-Aryl-Z-2-aroylmethylidene-1,2-dihydroquinoxalines react with oxalyl chloride to form 3-aryl-2-(2-aryl-4,5-dioxo-4,5-dihydro-3-furyl)quinoxalines, whose thermal decarbonylation generate 5-aryl-2-3(arylquinoxalin-2-yl)-4-aroyl-3-aroyloxy-1H-pyrido[1,2-a]quinoxalin-1-ones. The crystal and molecular structures of one of them (Ar = Ph) were established by X-ray diffraction analysis.     

Decyclization of 5-Aryl-4-methyl-2,3-dihydrofuran-2,3-diones by the Action of Nucleophiles

Ring cleavage in 4-methyl-5-phenyl-2,3-dihydrofuran-2,3-dione by the action of methanol and in 5-aryl-4-methyl-2,3-dihydrofuran-2,3-diones by the action of aniline and N-methylaniline results in formation of, respectively, methyl 3-methyl-4-phenyl-2,4-dioxobutanoate and 4-aryl-3-methyl-2,4-dioxobutananilides. The reaction mechanism was studied by ¹H NMR spectroscopy.     

Interaction of 5-Aryl-2,3-dihydrofuran-2,3-diones with Functionally Substituted Hydrazides and Diaminoglyoxal Diphenylhydrazone

The reaction of 5-aryl-2,3-dihydrofuran-2,3-diones with cyanoacetylhydrazide, o-(hydrazinocarbonyl)phenylthiourea, and the diphenylhydrazone of diaminoglyoxal leads to the synthesis of the corresponding N-cyanoacetylhydrazides of aroylpyruvic acids, 2-(N-aroylpyruvoylhydrazinocarbonyl)-phenylthioureas, and 5,6-bis(phenylhydrazono)-3-aroylmethylenepiperazin-2-ones. The results of the primary investigation of the biological activity of N-cyanoacetylhydrazides of aroylpyruvic acids are given.     

An Efficient,One-Pot Synthesis of Dialkyl 5-Hydroxy-4-aryl-2,5-dihydrofuran-2,3-dicarboxylate Derivatives

The reaction between arylglyoxalmonohydrates, dialkyl acetylenedicarboxylates, and triphenylphosphine is described as a simple and efficient method for the synthesis of 5-hydroxy-4-aryl-2,5-dihydrofuran-2,3-dicarboxylate derivatives.     

5-Arylfuran-2,3-diones

5-Arylfuran-2,3-diones were obtained by cyclization of aroylpyruvic acids in the presence of thionyl chloride. It is shown that the five-membered ring of 5-arylfuran-2,3-diones is unstable and is cleaved under mild conditions under the influence of nucleophilic reagents.     

Ring opening in 5-aryl-2,3-furandiones synthesis of aroylpyruvic acid esters

Aroylpyruvic acid esters are formed by the action of alcohols and phenol on 5-aryl-2,3-furandiones.Communication III from the series Chemistry of Oxalyl Derivatives of Methyl Ketones. See [1] for communication II.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1030–1031, August, 1977.     

Chemistry of 2-methylene-2,3-dihydrofuran-3-ones. 2. 2-Alkoxycarbonylmethylene-5-aryl-4-halo-2,3-dihydrofuran-3-ones: Synthesis,structure, and properties

Reaction of 5-aryl-4-halo-2,3-dihydrofuran-2,3-diones with alkoxycarbonylmethylenetriphenylphosphoranes has given 2-alkoxycarbonylmethylene-5-aryl-4-halo-2, 3-dihydrofuran-3-ones, which readily add halogens at the 2-exocyclic double bond, and on reaction with arylamines recyclize to give 2-hydroxy-2, 3-dihydropyrrol-3-ones.For Communication 1, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1034–1038, August, 1989.     

Mechanism of ring opening of cis- and trans-1-methyl-2-aryl-3-aroylaziridine perchlorates under the influence of alcohols

The corresponding threo- and erythro-1,3-diaryl-3-alkoxy-2-N-methylamino-1-propanones, which are formed regio- and stereospecifically, were obtained by the reaction of cis- and trans-1-methyl-2-aryl-3-aroylaziridine perchlorates with alcohols.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1054–1058, August, 1989.     

Site of nucleophilic attack and ring opening of five-membered heterocyclic 2,3-diones: a density functional theory study

The site of nucleophilic addition to five-membered heterocyclic 2,3-diones (4-iminomethylfuran-2,3-dione A1 and 4-formyl-pyrrole-2,3-dione B1) is studied by density functional theory calculations (B3LYP/6-31G) with water as the nucleophile. Both uncatalyzed and water-assisted 1,2-addition to the lactone (lactam) and the keto carbonyl group, and conjugate addition to C5 of the heterocycle and the heteroatom of the 4-iminomethyl (formyl) moiety are considered. In addition, concerted and stepwise ring fission of the lactone (lactam) ring is also treated. The effect of solvation (aqueous solution) is taken into account by the polarizable continuum model (PCM) and the Poisson-Boltzmann SCRF method (PB-SCRF), as well as explicit water molecules. Only this latter approach yields meaningful activation free energies. Barriers for addition of H2O increase in the order 1,4-addition to C5 < addition to the lactone (lactam) carbonyl < hydration of the 3-keto group. No reaction path for concerted water-assisted ring opening could be found.     

Five-Membered 2,3-Dioxo Heterocycles: XLV. Thermolysis of 5-Aryl-4-phenyl-2,3-dihydrofuran-2,3-diones in the Absence of Other Partners and in the Presence of Carbonyl Compounds

Aroyl(phenyl)ketenes generated by thermolysis of 5-aryl-4-phenyl-2,3-dihydrofuran-2,3-diones undergo [4+2]-cyclodimerization to 3-aroyl-6-aryl-3,5-diphenyl-3,4-dihydro-2H-pyran-2,4-diones. Heating of the latter leads to rearrangement with formation of 4-aroyloxy-6-aryl-3,5-diphenyl-2H-pyran-2-ones. Thermolysis of 5-aryl-4-phenyl-2,3-dihydrofuran-2,3-diones in the presence of carbonyl compounds yields 6-aryl-5-phenyl-4H-1,3-dioxin-4-ones.