Chemistry of oxalyl derivatives of methyl ketones. 28. Reaction of carbonyl compounds of adamantane with 5-phenyl-2,3--dihydrofuran-2,3-dione

The reaction of substituted methyl 1-adamantyl ketones with an equimolar amount of 5-phenyl-2,3-dihydrofuran-2,3-dione under the conditions of the thermal decarbonylation of the latter leads to the corresponding 2-methyl-2-adamantyl-6-pheny1-1,3-dioxen-4-ones, 6-phenyl-3-benzoyl-2,4-dione, and the starting ketones. The steric and electronic factors that affect the yields of the dioxen-4-ones were examined. -Hydroxymethyl 1-adamantyl ketones open up the furan ring to give 1-adamantoylmethyl benzoylpyruvate. Data from the IR, PMR, and UV spectra are presented.See [1] for communication 27.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1312–1315, October, 1982.     

Chemistry of oxalyl derivatives of methyl ketones

It was established by IR, UV, and PMR spectroscopy that 2-phenacylidenebenzo-1,4-thiazin-3-ones are formed in the reaction of o-aminothiophenol with aroylpyruvic acids or 5-arylfuran-2,3-diones. 2-Carbomethoxy-2-phenacyl-1,3-benzothiazolines were isolated in the reaction of o-aminothiophenol with aroylpyruvic acid esters.See [1] for communication IV.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 755–757, June, 1977.     

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.     

Synthesis of 5-R-3-Diphenylmethylene-2,3-dihydro-2-furanones from 5-Substituted 2,3-Dihydro-2,3-furandiones and Phenylbenzoyldiazomethane

3-Reactions of 5-aryl, 5-heteryl, and 5-styryl-2,3-dihydro-2,3-furandiones with phenylbenzoyldiazomethane gave rise to 5-substituted 3-dipenylmethylene-2,3-dihydro2-furanones. The possible intermediates and reaction products were investigated by semiempirical SCF MO LCAO method in AM1 approximation.     

Interaction of 5-aryl-4-quinoxalinyl-2,3-dihydro-2,3-furandiones with mesitylamine and methyl(phenyl)hydrazine. Synthesis and crystal and molecular structure of 2-(1-mesityl-4,5-dioxo-2-phenyl-4,5-dihydro-3-pyrollyl)-3-phenylquinoxaline

The interaction of 5-aryl-4-quinoxaline-2,3-dihydro-2,3-furandiones with mesitylamine and methyl(phenyl) hydrazine results in the formation of 1-substituted 5-aryl-4-quinoxalinyl-2,3-dihydro-2,3-pyrrolediones. The crystal and molecular structure of the 1-mesityl-5-phenyl derivative was investigated by X-ray diffraction.Original Russian Text Copyright © 2004 by Z. G. Aliev, N. Yu. Lisovenko, L. O. Atovmyan, and A. N. MaslivetzTranslated from Zhurnal Strukturnoi Khimii, Vol. 45, No. 3, pp. 553–557, May–June 2004.     

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

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

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.     

Investigation of the Interaction of 5-Aryl-2,3-dihydro-2,3-furandiones with Compounds Containing C=N and C≡N Bonds Simultaneously

Aroylketenes, generated by the thermolysis of 5-aryl-2,3-dihydro-2,3-furandiones, react with S-methyl-N-cyano-N′-phenylisothiourea, N-cyano-N′,N′-dimethylformamidine, and N,N-bis(β-cyanoethyl)-cyanamide with the formation of 6-aryl-2-[(methylthio)(phenylamino)methylene]amino-, 6-aryl-2-dimethylaminomethyleneamino-, and 6-aryl-2-[N,N-bis(β-cyanoethyl)amino]-4H-1,3-oxazin-4-ones respectively. Modeling has been carried out of the interaction of benzoylketene with the indicated cyano compounds by the SSP MO LCAO semiempirical method using the MNDO-PM3 approach. A mechanism is proposed for the formation of substituted 4H-1,3-oxazin-4-ones. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1490–1501, October, 2005.     

Five-membered 2,3-dioxo heterocycles: C. Reaction of methyl 1-aryl-3-cinnamoyl-4,5-dioxo-4,5-dihydro-1H-pyrrole-2-carbocylates with acyclic enamines

Methyl 1-aryl-3-cinnamoyl-4,5-dioxo-4,5-dihydro-1H-pyrrole-2-carbocylates react with N-substituted ethyl 3-amino-3-phenylprop-2-enoates, ethyl 3-aminobut-2-enoates, 3-amino-1,3-diphenylprop-2-en-1-ones, and dimethyl 2-arylaminofumarates to give 9-ethoxycarbonyl-, 9-benzoyl-, and 8,9-bis(methoxycarbonyl)-4-cinnamoyl-1,7-diazaspiro[4.4]nona-3,8-dienes.     

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 substituted 5-aminopyrimidines with oxalyl chloride

Depending on the reaction conditions and the substituents, N-(2,4,6-substituted 5-pyrimidinyl)oxamyl chlorides and N,N-di(2,4,6-substituted 5-pyrimidinyl)oxamides are formed in the reaction of 5-aminopyrimidines with oxalyl chloride.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 536–538, April, 1976.     

Reaction of methyl trifluoropyruvate with aryl amines

Conclusions We have found a novel reaction of primary and some secondary aryl amines with methyl trifluoropyruvate, which yields derivatives of 3-hydroxy-2-oxo-3-trifluoromethylindoline.For preliminary communication, see [1].Translated from Izvestiya Akademii-Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2080–2085, September, 1986.     

Mass spectral studies of some aryl and aroyl derivatives of glyoxime

Mass spectra of two diaroylglyoximes (Ia and Ib) are reported and compared with those of the corresponding dehydration products, 3,4-diaroyl-1,2,5-oxadiazoles (IIIa and IIIb, respectively). In Ia and Ib, unlike in diarylglyoximes (Id and Ie), the largest ion is [M — 18]⁺, but this does not form in the ion source by a simple thermal dehydration. Similar spectra have been obtained for an alkyl aroyl derivative of glyoxime (Ic) and an isonitroso-β-diketone (II). A specific electron-impact-induced rearrangement leading to the formation of carboxylic acids has been observed in the mass spectra of all the acylated oximes under investigation.     

Reaction of N3-aryl-1-adamantanecarboxamidrazones with aldehydes and ketones

Russian Journal of Organic Chemistry -     

Condensed thienopyrimidines. I. Synthesis and gastric antisecretory activity of 2,3-dihydro-5H-oxazolothienopyrimidin-5-one derivatives

A practical preparation of various 2,3-dihydro-5H-oxazolo[3,2-a]thieno[3,2-d]-, [3,4-d]-, and [2,3-d]pyrimidin-5-one derivatives was developed starting from the corresponding aminothiopheneesters in two steps, and their chloro-substituted derivatives were prepared. These compounds were evaluated for gastric antisecretory activity in pylorus-ligated rats, compared to the anti-ulcer standard, cimetidine, and their structure-activity relationships are discussed.