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. 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.     

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 -     

Kinetics of opening of the ring of 5-aryl-2,3-dihydrofuran-2,3-diones under the influence of methanol

The kinetics of the opening of the ring of 5-aryl-2,3-dihydrofuran-2,3-diones under the influence of methanol, which leads to the formation of methyl esters of aroylpyruvic acids, were studied by PMR spectroscopy. A mechanism is proposed for the reaction.Communication 26 from the series Chemistry of oxalyl derivatives of methyl ketones. See [1] for Communication 25.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 744–746, June, 1982.     

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.     

Five-membered 2,3-dioxoheterocycles: LXXXIII. Synthesis and thermolysis of 1-aryl-4,5-diaroyl-1<Emphasis Type="Italic">H</Emphasis>-pyrrole-2,3-diones

The reaction of (Z)-2-amino-1,4-diarylbut-2-en-1,4-diones with oxalyl chloride led to the formation of 1-aryl-4,5-diaroyl-1H-pyrrole-2,3-diones that at the thermal decarbonylation gave aroyl(N-arylimidoyl)ketenes which underwent stabilization by molecular cyclization into 2,3-diaroylquinolin-4(1H)-ones.     

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.     

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.     

The reactions of 5-aryl-2,3-dimethylisoxazolium salts with aromatic aldehydes

The reactions of the 3-methyl group in 5-aryl-2,3-dimethylisoxazolium tetrafluoroborates with aromatic aldehydes, in the presence of piperidine were studied. Isoxazolium salt reactivity is independent of the phenyl group substituent at C-5 on the isoxazolium salt ring. However, it does depend on the aldehyde structure.     

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.     

Five-membered 2,3-dioxoheterocycles: LXXXVII. [4+2]-cycloaddition of alkyl vinyl ethers and 3,4-dihydro-2H-pyran to 4,5-diaroyl-1 H-pyrrole-2,3-diones

1-Aryl-4,5-diaroyl-1H-pyrrole-2,3-diones react with alkyl vinyl ethers and 3,4-dihydro-2H-pyran affording 1,4-diaryl-7a-aroyl-6-ethoxy-7,7a-dihydropyrano[4,3-b]pyrrole-2,3(1H,6H)-diones and 1,4-diaryl-9baroyl-1,7,8,9,9a-hexahydro-5aH-pyrano[3??,2??:5,6]pyrano[4,3-b]-pyrrole-2,3-diones respectively.     

Five-membered 2,3-dioxoheterocycles: LXXIII. Synthesis and thermolysis of 3-acylpyrrolo[1,2-a]quinoxaline-1,2,4(5H)-triones

Reactions of (Z)-3-(phenacylidene-2-oxo)-3,4-dihydroquinoxalin-2(1H)-ones and (Z)-3-(3,3-dimethyl-2-oxobutylidene)-3,4-dihydroquinoxalin-2(1H)-one with oxalyl chloride led to the formation of 3-acyl-1Hpyrrolo[1,2-a]quinoxaline-1,2,4(5H)-triones that at the thermal decarbonylation generated acyl(3-oxoquinoxalin-2-yl)ketenes which underwent the intramolecular stabilization giving 3-acylfuro[3,2-b]quinoxalin-2(4H)-ones.     

Five-membered 2,3-dioxo heterocycles. 21. Reaction of 1,5-diaryl-4-ethoxycarbonyl-tetrahydropyrrole-2,3-diones with 2-aminopyridine

The reaction of 2-aminopyridine with 1,5-diaryl-4-ethoxycarbonyltetrahydropyrrole-2,3-diones gave 11 complexes, which are converted to N-(2-pyridyl)-1,5-diaryl-3-hydroxy-2-oxo-2,5-dihydropyrrole-4-carboxamides when they are heated above their melting points without a solvent. The character of the hydrogen bonds in the complexes obtained is discussed.See [1] for Communication 20.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 32–36, January, 1992.     

Five-membered 2,3-dioxo heterocycles: CIII. Spiro heterocyclization of 4,5-diaroyl-1H-pyrrole-2,3-diones with 3-aminobut-2-enenitrile

1-Aryl-4,5-diaroyl-1H-pyrrole-2,3-diones reacted with 3-aminobut-2-enenitrile to produce 1,6-diaryl-4-aroyl-3-hydroxy-8-methyl-2-oxo-1,7-diazaspiro[4.4]nona-3,6,8-triene-9-carbonitriles.