Michael condensation of 3-arylidene-3H-pyrrol-2-ones and 3-arylidene-3H-furan-2-ones with cyclohexanone

The Michael condensation in the series of 5-aryl-3-arylidene-3H-pyrrol-2-ones and 5-aryl-3-arylidene-3H-furan-2-ones, containing an activated C=C bond, with cyclohexanone was investigated. It was shown that the condensation products were 1,5-dicarbonyl compounds containing a heterocyclic fragment. The enolization of one of the oxo groups, leading to the formation of hydroxypyrrole or hydroxyfuran structures, was demonstrated by the spectral data. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 823–827, June, 2007.     

Bromination of 5-Substituted 3H-Furan-2-ones and 3H-Pyrrol-2-ones

The bromination of 5-alkyl(aryl)-3H-furan-2-ones and 5-alkyl(aryl)-3H-pyrrol-2-ones and also their derivatives takes place at the ethylene bond with the formation of 4-monobromo derivatives. N-Phenyl-3H-pyrrol-2-ones are brominated simultaneously at the ethylene bond of the heterocycle and at the phenyl substituent at the nitrogen atom.     

Arylmethylene derivatives of 5-R-3H-furan-2-ones and N-aryl-5-R-3H-pyrrol-2-ones in reaction with acetylacetone

Reaction with acetylacetone in the series of 3-arylmethylene-substituted furan-2-ones and pyrrol-2-ones was studied. 8-R-4-Acyl-5-aryl-3-oxo-9-oxabicyclo[4.3.0]nona-1,7-dienes and N-tolyl-8-R-4-acyl-5-aryl-3-oxo-9-azabicyclo[4.3.0]nona-1,7-dienes were synthesized. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, 1457–1462, October, 2007.     

Heterocyclization of Derivatives of 4-Oxoalkanoic Acids to 1,5-Disubstituted Pyrrolin-2-ones

Conditions were developed for the synthesis and production of 1-aryl-5-alkyl(aryl)-3H- and 1-aryl-5-alkyl(aryl)-5H-pyrrolin-2-ones from the amides and esters of 4-oxoalkanoic acids. It was established that the yield and ratio of the 3H and 5H isomers depend on the substrate employed in the reaction.     

Direct Synthesis of 4-Acetyl-1-alkyl-1H-pyrrol-2(5H)-ones from Difunctionalized Allyl Bromide

We describe a simple and efficient protocol for accessing some unsaturated heterocyclic compounds in a direct evaluation of allyl bromide as Z-ethyl 3-bromomethyl-4-oxopent-2-enoate. The latter reacts with primary amines via two successive nucleophilic substitutions followed by a 5-exo-trig cyclization to produce selectively 4-acetyl-1-alkyl-1H-pyrrol-2(5H)-ones in good yields.     

Synthesis of arylidene derivatives of N-unsubstituted pyrrolin-2-ones

5-Alkyl(aryl)-3-arylidene-3H-pyrrolin-2-ones were synthesized by ammonolysis of their O-heteroanalogs or by the reactions of 5-alkyl(aryl)-3H-pyrrolin-2-ones with aromatic aldehydes. The structures of the compounds obtained were confirmed by ¹H NMR spectra.     

Unexpected Synthesis of Novel 3-Allyl-5-(arylidene)-2-thioxo-thiazolidin-4-ones in Reactions of 3-Allylrhodanine with 2-Arylidene-4-methyl-5-oxopyrazolidinium Ylides

Abstract

The reaction of 3-allylrhodanine with 2-arylidene-4-methyl-5-oxopyrazolidinium ylides proceeded unexpectedly to form novel 3-allyl-5-(arylidene)-2-thioxo-thiazolidin-4-ones 6a–k in good yields. All structures have been formulated on the basis of their spectral (IR, NMR, MS) data and elemental analyses. In addition, the structure of compound 6a was confirmed by means of x-ray crystallographic analysis.     

Reactivity of pyrrol-2-ones. (review)

Published data on the chemical transformations of pyrrol-2-ones are reviewed and analyzed. The extensive synthetic possibilities of compounds containing a pyrrolone ring in the synthesis of various heterocyclic compounds with complex structures are demonstrated. The reactions are arranged according to the reaction centers of the pyrrol-2-ones: The methylene unit, the C=C double bond, the electron-deficient carbon atom of the carbonyl group.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1443–1463, October, 2004.     

Reactions of sulfonamides with 4,5-dihydroxyimidazolidin-2-ones

The interaction of sulfonamides with 4,5-dihydroxyimidazolidin-2-ones was studied for the first time. The earlier unknown 4,4′-sulfonyldiiminobis(1,3-dialkylimidazolidin-2-ones) and 4(5)-aryl(alkyl)-sulfonyliminoimidazolidin-2-ones were synthesized. A probable pathway of the reaction was proposed. 1,3-Diethyl-4,5-dihydroxyimidazolidin-2-one was isolated and described. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1604–1607, August, 1998.     

Camps reaction for the synthesis of 3-RS-4-arylquinolin-2-ones

The replacement of the chlorine atom in 2-(chloroacetamido)benzophenones on treatment with RSH (R = Alk, Ar, Hetaryl) in the presence of MeONa is accompanied by intramolecular cyclization following the Camps reaction pattern to give 3-RS-4-arylquinolin-2-ones. Cleavage of 4-aryl-3-(benzoxazol-2-ylthio)quinolin-2-ones by morpholine has resulted in the corresponding 4-aryl-3-mercaptoquinolin-2-ones.     

Nucleophilic Addition of Amines to N-Aryl-substituted Pyrrolin-2-ones

The nucleophilic addition of n-butyl- and benzylamines to 1-(4-nitrophenyl)-5H-pyrrolin-5-one and 1-(4-sulfamoylphenyl)-5H-pyrrolin-2-one at 50°C in an excess of the amines with the formation of N-substituted amides of 3-alkyl(benzyl)amino-4-(4-R-anilino)butyric acids was investigated. The N-substituted amides of 3-arylamino-4-hydroxybutyric and 4-hydroxy-2-butenoic acids were synthesized from 2(5H)-furanone and aromatic amines (1:3) at 180°C. 4-Alkylamino-1-(4-nitrophenyl)pyrrolid-2-ones were obtained in the reaction of 1-(4-nitrophenyl)-5-pyrrolin-2-one with ammonia or aliphatic, alicyclic, and aromatic amines (1:3, 90°C, in DMF).     

Synthesis of 2-Benzylidene and 2-Hetarylmethyl Derivatives of 2H-1,4-Benzoxazin-3-(4H)-ones as Neuroprotecting Agents

A wide variety of the title compounds were synthesized by conventional and microwave methods in which the main step is a condensation of an aldehyde with a 1,4-benzoxazin-3-(4H)-one. In all cases, the Z diasteromers were the major products. Of particular importance is the synthesis of novel 2-(3,5-dibromo-4-hydroxy) and 2-(4-acetoxy-3,5-dibromobenzylidene derivatives of 2H-1,4-benzoxazin-3-(4H)-ones, four of which were shown in a previous publication to exhibit potent neuroprotecting properties. The yields of titled compounds ranged from 25 to 83%.     

Reaction of 2-(2-oxoethylidene)furan-3(2H)-ones with isopropylidenehydrazides of aromatic carboxylic acids: Synthesis of 3-hydroxy-3-(2-oxoethyl)-2,3-dihydropyridazin-4(1H)-ones

3-Hydroxy-3-(2-oxoethyl)-6-phenyl-2,3-dihydropyridazin-4(1H)-ones were obtained by the reaction of methyl 3-oxo-5-phenylfuran-2(3H)-ylideneacetate or 2-[2-(4-chlorophenyl)-2-oxoethylidene]-5-phenylfuran-3(2H)-one with benzoic or p-nitrobenzoic isopropylidenehydrazides. Equilibrium C₍₅₎H and C₍₅₎H₂ tautomeric forms were detected in solutions of the 4-chlorophenyl derivatives in DMSO-d₆. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1156–1158, August, 2007.     

Reaction of 1-Aryl-3-methylpyrazol-5-ones with 2-Cyanoaryldiazonium Bisulfates

2-Cyanoaryldiazonium bisulfates, obtained by the action of nitrosyl sulfuric acid on isatin 3-hydrazone and its 5-bromo and 5-nitro derivatives, couple with 1-aryl-3-methylpyrazol-5-ones and form 4-arylhydrazones of 1-aryl-3-methylpyrazole-4,5-diones. It was established on the basis of data of IR, UV, and ¹H NMR spectra and of X-ray structural analysis that the coupling products exist in the hydrazone form stabilized by an intramolecular hydrogen bond.__________Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 210–215, February, 2005.     

Effective synthesis of 5-aryl-3-ethylidene-3H-pyrrol-2-ones

Substituted 5-aryl-3-ethylidene-3H-pyrrol-2-ones were synthesized by the reaction of the corresponding 4-aryl-4-oxobutanoic acids with ketones in the presence of aminating agents. The conditions of this reaction were developed with the use of both the conventional condensation technique and microwave activation. The structures of the reaction products were con-firmed by elemental analysis, IR spectroscopy, and ¹H NMR spectroscopy. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 693–696, April, 2006.     

Synthesis, Structure, and Chemical Properties of N-Substituted 2(3)-Imino-2,3-dihydrofuran-3(2)-ones. (Review)

Published data on the synthesis, structure, and chemical properties of N-substituted 2(3)-imino-2,3-dihydrofuran-3(2)-ones to 2002 are reviewed     

Reaction of 3-Arylmethylidene-3H-furan-2-ones with 3-Amino-1,2,4-triazole as a Convenient Technique to Synthesize Condensed Diazepinones

The interaction of the arylmethylidene derivatives of 3H-furan-2-ones with 3-amino-1,2,4-triazole was studied. The structure of the final products depends on reaction conditions and reagent ratio.

Synthesis of Some Heterocyclic Compounds from Enamines of 3-Acetylfuran-2(5 H)-ones

The interaction of different 3-acetylfuran-2(5H)-ones (1, 4) with dimethylformamide dimethyl acetal (DMF/DMA) has been investigated, and the condensed furopyridine system 3 was obtained. By means of interaction of compounds 4 and DMF/DMA via the 3-acetylfuran-2(5H)-one enamines, the heterocyclic substituted furanones are obtained. The condensation of 3-acetyl-4,5,5-trimethylfuran-2(5H)-one (1a) with veratraldehyde was realized. Through the interaction of 1a with malononitrile and further intramolecular condensation of the product, 6-amino-dihydroisobenzofuran-5-carbonitrile was also synthesized.     

Synthesis of 5-Formyl and 5-Acyl-1,2-dithiole-3-ones

The preparation of new 5-formyl-, 5-acetyl- and 5-propionyl-1,2-dithiole-3-ones by oxidation of the corresponding 1,2-dithiole-3-thiones with mercuric acetate is described.     

2-芳基-5-(5-苯基-2H-四唑-2-亚甲基)-1,3,4-噁二唑类化合物的研究

作者曾研究2-芳基-5-(2-苯基-4-喹啉基)-1,3,4-噁二唑类衍生物,并发现它们具有促进小麦发芽生长的功效。Juby和Shan等报道某些四唑类化合物具有消炎性