- Cyclization of α-hydroxy-β-diketones to furan-3(2H)-ones under mild basic conditions
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In relation with studies directed to the total synthesis of psuerotin A, conversion of α-hydroxy-β-diketones to the correspponding furan-3(2H)-ones have been successfully performed by a new method using K2CO3 in methanol. Cyclization
- Shao,Tamm
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- 3(2H)-Furanones from Mercuric Acetate Oxidation of Allenic Ketones. A Synthesis of Bullatenone
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Treatment of allenic ketones 1 with mercuric acetate yields 3(2H)-furanones 2 (90+percent).The oxidation of 1c constitutes a new synthesis of bullatenone (2c).
- Wolff, Steven,Agosta, William C.
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- Synthesis of a 3(2H)-Furanone Derivative from Propargylic Alcohol, CO, and Phenyl Halide Catalyzed by Transition Metal Complexes
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2-Methyl-3-butyn-2-ol reacted with CO and phenyl halides in the presence of a catalytic amount of transition metal complexes to afford 2,2-dimethyl-5-phenyl-3(2H)-furanone (bullatenone) under the influence of CO2.
- Inoue, Yoshio,Taniguchi, Masaaki,Hashimoto, Harukichi,Ohuchi, Kunihiro,Imaizumi, Shin
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- Facile synthesis of 3(2H)-furanones
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Abstract: A practical method for the synthesis of 3(2H)-furanones including the bullatenone was described. Intramolecular cyclization of 4-hydroxyalkynones in the presence of KOH affords the biologically potent furanones in moderate-to-good yield at room temperature. Synthesis of 4-hydroxyalkynones from the reaction of acid chloride and terminal alkyne in the presence of copper iodide at room temperature was also reported.
- Panda, Niranjan,Nayak, Dinesh K.
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p. 1093 - 1100
(2018/02/22)
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- Synthesis of 5-Aryl-3(2 H)-furanones Using Intramolecular Cyclization of Sulfonium Salts
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Base-induced intramolecular cyclization of novel (4-aryl-2,4-dioxobutyl)methylphenylsulfonium salts prepared from the commercially available 1-arylethanone by a cost-effective process is described in this paper. The reaction was completed within 10 min to produce a family of 2-unsubstituted 5-aryl-3(2H)-furanones in excellent yield. This procedure is simple, and can be carried out under mild conditions and an ambient atmosphere.
- Inagaki, Sho,Saito, Kai,Suto, Soichiro,Aihara, Hiromi,Sugawara, Aoi,Tamura, Satoru,Kawano, Tomikazu
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p. 13834 - 13846
(2018/11/23)
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- Cationic gold(I)-catalyzed intramolecular cyclization of γ-hydroxyalkynones into 3(2H)-furanones
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"Chemical Equation Presented" The combination of (p-CF 3C6H4)3PAuCl and AgOTf generates a powerful catalyst for the intramolecular cyclizations of readily available y-hydroxyalkynones un-der mild conditions. The
- Egi, Masahiro,Azechi, Kenji,Saneto, Moriaki,Shimizu, Kaori,Akai, Shuji
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supporting information; experimental part
p. 2123 - 2126
(2010/06/12)
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- Synthesis of heterocyclic systems by transition-metal-catalyzed cyclization-migration reactions - A diversity-oriented strategy for the construction of spirocyclic 3(2H)-furanones and 3-pyrrolones
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Two platinum(II)-catalyzed heterocyclization-migration reactions that provide five-membered heterocycle products are described. With 5 mol-% of PtCl2 as a catalyst, 2-alkynyl-2-hydroxy carbonyl compounds 1 are converted into 3(2H)-furanones 2 a
- Binder, Joerg T.,Crone, Benedikt,Kirsch, Stefan F.,Liebert, Clemence,Menz, Helge
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p. 1636 - 1647
(2008/02/06)
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- Pd(II)-catalyzed cascade Wacker-Heck reaction: Chemoselective coupling of two electron-deficient reactants
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A novel palladium(II)-catalyzed oxy-carbopalladation process was developed allowing for the orchestrated union of hydroxyynones with ethyl acrylate, two electron-deficient reactants. With β-hydroxy ynones, this cascade Wacker-Heck process gave access to highly functionalized tri- or tetrasubstituted dihydropyranones featuring an unusual dienic system. For diastereomerically pure and for enantioenriched β-hydroxyynones, these reactions proceed without affecting the stereochemical integrity of the existing stereocenters. In addition, tetrasubstituted furanones can be prepared when α-hydroxyynones and ethyl acrylate are used as starting materials. The dihydropyranones and furanones obtained upon cyclization are novel compounds, but structurally related carbohydrate derivatives featuring a similar dienic system have been used as starting materials for the construction of polyannulated products, suggesting that these cascade Pd(II)-mediated oxidative heterocyclizations are of value for various synthetic applications.
- Silva, Franck,Reiter, Maud,Mills-Webb, Rebecca,Sawicki, Marcin,Klaer, Daniel,Bensel, Nicolas,Wagner, Alain,Gouverneur, Veronique
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p. 8390 - 8394
(2007/10/03)
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- Synthesis of acetylenic ketones by a Pd-catalyzed carbonylative three-component coupling reaction in [bmim]PF6
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A carbonylative three-component coupling reaction of aryl iodides with terminal alkynes catalyzed by PdCl2(PPh3)2 was carried out using an ionic liquid, [bmim]PF6, as the reaction medium, which resulted in good yields of α,β-acetylenic ketones. The low-viscosity ionic liquid, [bmim]NTf2, was not suitable for this reaction, since the background Sonogashira coupling reaction, a competing reaction, also proceeded.
- Fukuyama, Takahide,Yamaura, Ryo,Ryu, Ilhyong
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p. 711 - 715
(2007/10/03)
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- Palladium-catalyzed oxidative cyclizations: Synthesis of dihydropyranones and furanones
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A boron-mediated syn- and anti-stereoselective aldol reaction giving rise to various β-hydroxyenones was coupled to a Pd(II)-mediated oxidative cyclization to give 2,3,6-trisubstituted syn- and antidihydropyranones in good yields. The Pd(I
- Reiter, Maud,Turner, Hazel,Mills-Webb, Rebecca,Gouverneur, Veronique
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p. 8478 - 8485
(2007/10/03)
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- Cyclisations of benzenesulfenyl chloride adducts with conjugated silyloxyenones: A new stereoselective reaction in the synthesis of 4,5-dihydrofuran-3(2H)-ones
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Adducts, generated in situ from E-α′-trialkylsilyloxy-α,β-unsaturated ketones with benzenesulfenyl chloride, cyclise in the presence of dry silica or zinc bromide to produce phenylsulfanyl substituted 4,5-dihydrofuran-3(2H)-ones with high stereoselectivity; oxidative elimination of the phenylsulfanyl group completes a new route to furan-3(2H)-ones.
- Colins, Conor C.,Cronin, Michael F.,Moynihan, Humphrey A.,McCarthy, Daniel G.
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p. 1267 - 1269
(2007/10/03)
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- An abnormal reaction of esters of 3-hydroxy-3-methylbutan-2-one. A rapid synthesis of bullatenone and geiparvarin
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A new rapid and facile synthesis of two natural products with the structure of3(2H)furanone is described by a cyclisation catalysed by cesium fluoride.
- Villemin, Didier,Jaffres, Paul-Alain,Hachemi, Messaoud
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p. 537 - 538
(2007/10/03)
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- Synthesis and antiulcer activity of novel 5-(2-ethenyl substituted)-3(2H)- furanones
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In order to investigate new antiulcer agents, spizofurone 1 (AG-629) was fragmented and reassembled to generate 5-phenyl-2,2-dimethyl-3(2H)-furanone (bullatenone, 2). Because of the antiulcer activity of 2,5-phenyl-substituted 2,2-dimethyl-3(2H)-furanones (3-6) were made and shown to have poor activity. Insertion of an ethenyl link between the furanone and phenyl rings gave 5-(2- phenylethenyl)-2,2-dimethyl-3(2H)-furanone (7). This compound had better activity than 2. Compounds 8-41 were synthesized to evaluate the SAR in 5-(2- ethenyl substituted)-3(2H)-furanones. Electron-withdrawing substituents on the aromatic ring (8, 10, 19, and 20) gave 2-3-fold higher activity. Further increases in the activity were found when the phenyl ring was replaced by heterocyclic nuclei. Compounds that contained a thiophene (29), pyridine (24- 26), or quinoline ring (32) had the best activity. Replacement of the methyl group on the furanone ring with a phenyl (34) or p-fluorophenyl (40) substituent in the 2-pyridine series gave compounds with activity that ranked with the best obtained in this study. The best compounds from the above SAR studies were evaluated in the ethanol-necrosis model for duration of cytoprotection action. Compounds 19, 24, and 29, which had the best duration of action, were tested with AG-629 in the acidified aspirin and indomethacin- induced lesion models. Only compound 24 had equivalent activity with AG-629 in both models.
- Felman,Jirkovsky,Memoli,Borella,Wells,Russell,Ward
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p. 1183 - 1190
(2007/10/02)
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- α-Methylene Cyclic Carbonate as a Conjunctive Agent for Aromatic Aldehydes
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α-Methylene cyclic carbonate undervent dacarboxylative cycliaddition to aromatic aldehydes to yield dihydrofuranone derivatives in the presence of a dicationic palladium complex.
- Inoue, Yoshio,Matsushita, Koichi,Yen, I-Fang,Imaizumi, Shin
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p. 1377 - 1378
(2007/10/02)
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- Rhodium Acetate Catalyzes the Addition of Carbenoids α- to Ether Oxygens
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Diazo-carbonyl compounds, when catalyzed by rhodium acetate, insert preferentially adjacent to ether oxygens.This phenomenon was exploited to develop a synthesis of 3(2H)-furanones.
- Adams, Julian,Poupart, Marc-Andre,Grenier, Louis,Schaller, Chris,Ouimet, Nathalie,Frenette, Richard
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p. 1749 - 1752
(2007/10/02)
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- Ring Closure to Ynone Systems: 5- and 6-endo- and -exo-dig Modes
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The rates of cyclisation of 2-hydroxy-2-methyl-5-arylpent-4-yn-3-ones in trifluoroacetic acid are reported.An approximate ρ value of -4.0 (using ?+) and a kinetic isotope effect KTFA/KTFA-d' of 4.2 are observed, which suggest that the reaction proceeds via rate-limiting triple-bond protonation and does not entail carbonyl protonation along the reaction co-ordinate.The base-catalysed ring closure occurs via the vinilyc carbanion.A similar mechanistic picture appears to be involved in the cyclisation of 1-(2-hydroxyphenyl)-3-arylprop-2-yn-1-ones which yield a mixture of flavone and aurone in base, whilst in acid only the flavone is observed.In contrast with recent theoretical studies, the base-catalysed results appear to conform to Baldwin's original proposal of acute-angle approach of a nucleophile to a triple bond.
- Brennan, Colin M.,Johnson, David C.,McDonnell Peter D.
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p. 957 - 962
(2007/10/02)
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- A NEW AND FACILE SYNTHESIS OF 3(2H)-FURANONES VIA CARBOXYLATION-DECARBOXYLATION SEQUENCE
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One-pot synthesis of 3(2H)-furanones from α-ethynyl tertiary alcohols and acyl halides has been achieved in the presence of a palladium complex under CO2 pressure.
- Inoue, Yoshio,Ohuchi, Kunihiro,Imaizumi, Shin
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p. 5941 - 5942
(2007/10/02)
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- The Intramolecular Wadsworth-Emmons Condensation of γ-(Acyloxy)-β-ketophosphonates. A New Route to 3(2H)-Furanones
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A series of γ-(acyloxy)-β-ketophosphonates has been synthesized, either from the corresponding α-iodo keto ester by an Arbuzov reaction or by acylation of an alkylphosphonate anion.When treated with potassium carbonate in DMF, these γ-(acyloxy)-β-ketophos
- Sampson, Paul,Roussis, Vassilios,Drtina, Gary J.,Koerwitz, Frederick L.,Wiemer, David F.
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p. 2525 - 2529
(2007/10/02)
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- A Novel and Practical Synthetic Method of 3(2H)-Furanone Derivatives
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A novel convenient synthetic method of 5-aryl-2,2-dimethyl-3(2H)-furanones (aryl = C6H5, 2-CH3C6H4, 3-CH3C6H4, 4-CH3C6H4, 2-ClC6H4, 4-ClC6H4, 2,4-Cl2C6H3) is described.It involves the Claisen-Schmidt condensation (potassium hydroxide/ethanol) of aromatic
- Sakai, Takashi,Yamawaki, Akitoshi,Ito, Hiroshi,Utaka, Masanori,Takeda, Akira
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p. 1199 - 1201
(2007/10/02)
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- ANIONIC ACTIVATION BY FLUORIDE ION IN SOLID-LIQUID SYSTEMS. SYNTHESIS OF 3 (2H)-FURANONES AND 2 (5H)-FURANONES.
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The evolution of 2-acyloxy 2-methyl 3-oxobutanamides 1 and 2-acyloxy 3-oxo 2,3-diphenylpropanamides 13 under anionic activation by cesium fluoride was studied.The fluoride ion is an efficient base for the heterocyclization of 1 into 3 (2H)-furanones and 2 (5H)-furanones, but the hydrolysis of the ester group lowered the selectivity of the reaction.However, the cleavage of 13 into the esters 14 and the cyclization of 3-benzoyloxy 3-methyl 2-butanone into bullatenone are very selective.
- Sebti, S.,Foucaud, A.
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p. 1361 - 1368
(2007/10/02)
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- A CONDENSED SYNTHESIS OF DIHYDRO-3(2H)-FURANONE
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A straight forward synthesis of dihydro-3(2H)-furanone is described.An attempted preparation of the oxetan-3-one precursor 10 by this method gave, instead, the ring enlargement product 11.
- Tarnchompoo, Bonkoch,Thebtaranonth, Yodhathai
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p. 5567 - 5570
(2007/10/02)
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- Novel Routes to Furan-3(2H)-ones. New Synthesis of Bullatenone and Geiparvarin
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New convenient versatile routes to the furan-3(2H)-one nucleus are described as exemplified by the synthesis of the two natural products bullatenone (1) and geiparvarin (2).The key step involves the hydration and cyclisation of the corresponding readily a
- Jackson, Richard F. W.,Raphael, Ralph A.
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p. 535 - 539
(2007/10/02)
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- ETHYL 5-SUBSTITUTED-3-ISOXAZOLECARBOXYLATES AS STARTING MATERIALS FOR A CONVENIENT ROUTE TO 3(2H)FURANONES AND 3(2H)IMINOFURANES.
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Cyclodehydration of γ-hydroxy-β-enaminoketones derived from 5-substituted-3-isoxazolemethanols leads to 3(2H)furanones or 3(2H)iminofuranes depending on the substitution pattern and on the reaction conditions.
- Baraldi, Pier Giovanni,Barco, Achille,Benetti, Simonetta,Manfredini, Stefano,Pollini, Gian Piero,Simoni, Daniele
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p. 4313 - 4316
(2007/10/02)
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- REDUCTION OF Δ2-ISOXAZOLINES-2. A FACILE SYNTHESIS OF 3(2H)-FURANONES.
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A simple synthesis of the 3(2H)-furanone ring system is described.
- Curran, Dennis P.,Singleton, David H.
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p. 2079 - 2082
(2007/10/02)
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- NEW METHODS FOR THE SYNTHESIS OF 3(2H)-FURANONES AND 2(5H)-FURANONES.
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New procedures for the synthesis of 3(2H)-furanones and 4-alkoxy-2(5H)-furanones are reported. Reaction of ketones with the lithium salt of propynal diethyl acetal, followed by treatment of the resulting 4-hydroxy-2-alkynal diethyl acetals with sulfuric a
- Saimoto,Shinoda,Matsubara,Oshima,Hiyama,Nozaki
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p. 3088 - 3092
(2007/10/02)
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- Regiocontrolled Formation of 4,5-Dihydro-3(2H)-furanones from 2-Butyne-1,4-diol Derivatives. Synthesis of Bullatenone and Geiparvarin
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Two new methods for selective hydration of 1,1,4-trisubstituted 2-butyne-1,4-diols (1) to give 4,5-dihydro-3(2H)-furanone derivatives are reported.The first involves selective monoacetylation of the less hindered hydroxyl group of 1 followed by Ag(I)-cata
- Saimoto, Hiroyuki,Hiyama, Tamejiro,Nozaki, Hitosi
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p. 3078 - 3087
(2007/10/02)
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- A FACILE SYNTHESIS OF 4-PHENYLTHIO-2(5H)-FURANONE DERIVATIVES. SYNTHESIS OF SESQUIROSE FURAN AND BULLATENONE
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Condensation of the dianions derived from E-3-(phenylthio)prop-2-enoic acid and its 2-methyl homologue with aldehydes and ketones provides a facile one step synthesis of 5-substituted 4-phenylthio-2(5H)-furanone derivatives.The application to the synthesi
- Takahashi, Yasuhiro,Hagiwara, Hisahiro,Uda, Hisashi,Kosugi, Hiroshi
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p. 225 - 229
(2007/10/02)
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- Synthesis and Reactions of Simple 3(2H)-Furanones
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Interest in the total synthesis of natural product antitumor agents which have as a central structural element the 3(2H)-furanone ring system has led to the development of an efficient general synthesis of a variety of simple 3(2H)-furanones.The strategy
- Smith, Amos B.,Levenberg, Patricia A.,Jerris, Paula J.,Scarborough, Robert M.,Wovkulich, Peter M.
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p. 1501 - 1513
(2007/10/02)
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- Synthesis of functionalized tetrahydrofurans
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A novel cyclization reaction is described which affords readily manipulable 3(2H)-dihydrofuranone ethylene ketals, useful in the total synthesis of an ascofuranone model, bullatenone, and muscarine analogs.
- Semple, J.Edward,Guthrie, Anne E.,Joullie, Madeleine M.
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p. 4561 - 4564
(2007/10/02)
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