2(5H)-Furanone and 5-Hydroxy-2(5H)-furanone: Reactions and Syntheses Based on Them

Russian Journal of General Chemistry - This review summarizes the data on 2(5H)-furanone, 5-hydroxy-2(5H)-furanone, and some substituted hydrofuranones with respect to their poorly studied or...     

Synthesis of 2-(2-arylamino-3-alkyloxazolidynyl-4)- and 2-(2-arylamino-3-alkylthiazolidynyl-4-N-alkylacetamides from 2(5H)-furanone

Aminolysis of 2(5H)-furanone leads to 3-alkylamino-4-hydroxy-N-alkylbutyramides which easily form hydroxy derivatives of thiourea. The latter, depending on the protonation or quaternization site, easily undergo cyclization to thiazolidine and oxazolidine derivatives.Translated from Khimiya Geterotsiklicheskilch Soedinenii No. 12, pp. 1629–1632, December, 1985.     

Substituted Butanolides and Butenolides: XVI. Oxidative and Hydrolytic Transformations of Butanolide Fused to Dihydropyrazole Ring

Reactions of 3a,4,6,6a-tetrahydro-3H-furo[3,4-c]pyrazol-6-one with chlorine and bromine give the corresponding 2,6-dihydro-4H-furo[3,4-c]pyrazol-6-one hydrohalides. Hydrolysis of 3a,4,6,6a-tetrahydro-3H-furo[3,4-c]pyrazol-6-one is accompanied by oxidation of the dihydropyrazole ring to pyrazole and opening of the lactone ring.     

Syntheses based on furancarboxylic acid amides. 1. Synthesis and structure of 2-(5-R-2-furyl)-4-oxoquinazolines

2-(5-R-2-Furyl)-4-oxoquinazolines are formed in the condensation of furancarboxylic acid primary amides with anthranilic acid in the presence of phosphorus oxychloride. It was determined by x-ray diffraction analysis, IR and PMR spectroscopy, and mass spectrometry that a labile hydrogen atom is bonded to the nitrogen atom in the 3-position and that the molecule has an s-NH,0-trans conformation.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1463–1466, November, 1989.     

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 new heterocyclic compounds based on n-benzyl(heptyl)-3-benzyl(heiityl)amino-4hydroxybutanamide

New derivatives of 1, 3-oxazolidine, 1,3-oxazolidin-2-one, 1,2,3-oxathiazolidin-2-one, and morpholine-2,3-dione respectively, containing the CH₂CONHR group, have been prepared by Me reactions of N-benzyl(heptyl)-3benzyl(hepiyl amino-4-hydroxybutanamide with 5-iodofurfural, ethyl trichloroacetate, thionyl chloride, and diethyl oxalate. The biological activity of the new compounds has been studied.Kuban State Technical University, Krasnodar 350072. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 711–716, May, 1996. Original article submitted January 29, 1996.     

Catalytic Oxidation of Furan and Hydrofuran Compounds. 7. Production of 2(5H)-Furanone by Oxidation of Furfural with Hydrogen Peroxide and Some of Its Transformations in Aqueous Solutions

Data on the synthesis of 2(5H)-furanone by the oxidation of furfural with aqueous hydrogen peroxide under the conditions of autocatalysis by the accumulating acids and also in the presence of catalytic amounts of Cr(VI) and Mo(VI) compounds are presented. Some transformations of 2(5H)-furanone in aqueous solutions are studied: hydrolysis, oxidation by potassium permanganate, complex formation with the ions of certain d-metals.