- 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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- 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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- Thermal addition reaction of aroylketene with 1-aryl-1- trimethylsilyloxyethylenes: Aromatic substituent effects of aroylketene and aryltrimethylsilyloxyethylene on their reactivity
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The thermal addition reaction of various aroylketenes (C) generated by the thermolysis of 5-aryldioxofurans (A) to 1-aryl-1-trimethylsilyloxyethylenes gave 1,5-diarylpentane-1,3,5-triones (D) and 2,6-diaryl-4H-pyran-4-ones (E). The introduction of electron withdrawing substituents in the aroylketene and of electron donating substituents facilitated the addition reaction. The observed substituent effects and the reaction mechanism are interpreted in terms of molecular orbital analyses.
- Saitoh,Oyama,Sakurai,Niimura,Hinata,Horiguchi,Toda,Sano
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p. 956 - 966
(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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