- Furan-2,3-diones as masked dipoles: synthesis of isotetronic acids and mechanistic considerations
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The formal dipolar behaviour of furan-2,3-diones is illustrated by their reaction with ethyl glyoxylate under Lewis basic activation uniquely, giving access to isotetronic derivatives. The Janus-type nature of the activated species, both nucleophilic and
- Barbier, Vincent,Couty, Fran?ois,David, Olivier R.P.
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p. 5646 - 5651
(2016/08/17)
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- Diphenylparabanic acid as a synthon for the synthesis of α-diketones and α-ketocarboxylic acids
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Diphenylparabanic acid was found to react with >2 equiv of organolithiums at -78 °C to effectively give the corresponding symmetrical α-diketones. However, upon treatment with 1 equiv of organolithium, the parabanic acid gave mainly 5-substituted 5-hydroxyimidazolidine-2,4-diones. On the other hand, Grignard reagents were less reactive toward the parabanic acid at low temperature, and selectively gave the corresponding 5- hydroxyimidazolidine-2,4-diones even if more than 1 equiv of the reagents was used. A tandem process in which the parabanic acid was first reacted with a Grignard reagent and then reacted in one-pot with an organolithium effectively gave the unsymmetrical α-diketone. 5-Substituted 5-hydroxyimidazolidine-2, 4-diones were useful as versatile precursors for preparing α- ketocarboxylic acids as well as unsymmetrical α-diketones.
- Watanabe, Nobuko,Hamano, Mitsutaka,Todaka, Shota,Asaeda, Takahiro,Ijuin, Hisako K.,Matsumoto, Masakatsu
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p. 632 - 639
(2012/03/22)
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- Reactions of acylpyruvic acids and 2,3-dihydrofuran-2,3-diones with 2,3-diaminopyridine
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Acylpyruvic acids readily react with 2,3-diaminopyridine to form (Z)-3-acylmethylene-1H-3,4-dihydropyrido[2,3-b]pyrazin-2-ones. 5-Aryl-2,3-dihydrofuran-2,3-diones which can be regarded as lactones derived from γ-enolized aroylpyruvic acids react with 2,3-diaminopyridine under mild conditions, yielding regioisomeric (Z)-2-aroylmethylene-4H-1,2-dihydropyrido[2,3-b]pyrazin-3-ones. The structure of the products and reaction chemoselectivity are discussed.
- Sof'ina,Igidov,Koz'minykh,Trapeznikova,Kasatkina,Koz'minykh
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p. 1017 - 1025
(2007/10/03)
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- 1,3,4,6-Tetracarbonyl compounds. 3. Synthesis, structural features, and antimicrobial activity of 1,6-diaryl-3,4-dihydroxy-2,4-hexadiene-1,6-diones
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The Wittig reaction of 5-aryl-2,3-dihydro-2,3-furandiones with aroylmethylenetriphenylphosphoranes is regioselective and leads to the formation of 5-aryl-2-aroylmethylene-2,3-dihydro-3-furanones. In the presence of acid the products react with water, givi
- Igidov,Koz'minykh,Sof'ina,Shironina,Koz'minykh
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p. 1276 - 1285
(2007/10/03)
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- Reactions of 5-aryl-furan-2,3-diones with acylmethylenetriphenylphosphoranes: Synthesis and biological activity of 3(2H)-furanone derivatives
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The Wittig reaction of 5-aryl-furan-2,3-diones 1 with acylmethylenetriphenylphosphoranes 2 conducted by heating under reflux in benzene solutions, proceeded regiospecifically to afford 2-acylmethylene-5-aryl-3(2H)-furanones 5 in good yields. When the star
- Kozminykh,Igidov,Kozminykh,Aliev
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- Synthesis and 13C FT NMR spectroscopy of furan-2,3-dione derivatives
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Substituted furan-2,3-diones were obtained by condensation of oxalyl chloride with silyl enol ether of para-substituted acetophenones (R = H, CH3, OCH3, Cl, Br, F), propiophenone, 1-tetralone, 6-methoxytetralone and 1-benzosuberone.The spectroscopic data obtained from IR, UV, 1H and 13C NMR studies are quite similar whichever are the substituents. furan-2,3-dione / 1H and 13C NMR / UV and IR spectra
- Hnach, M.,Aycard, J. P.,Zineddine, H.
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p. 393 - 396
(2007/10/02)
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