493-71-0Relevant academic research and scientific papers
Cyclization of α-hydroxy-β-diketones to furan-3(2H)-ones under mild basic conditions
Shao,Tamm
, p. 2891 - 2892 (1991)
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
3(2H)-Furanones from Mercuric Acetate Oxidation of Allenic Ketones. A Synthesis of Bullatenone
Wolff, Steven,Agosta, William C.
, p. 703 - 704 (1985)
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).
Synthesis of a 3(2H)-Furanone Derivative from Propargylic Alcohol, CO, and Phenyl Halide Catalyzed by Transition Metal Complexes
Inoue, Yoshio,Taniguchi, Masaaki,Hashimoto, Harukichi,Ohuchi, Kunihiro,Imaizumi, Shin
, p. 81 - 82 (1988)
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.
Facile synthesis of 3(2H)-furanones
Panda, Niranjan,Nayak, Dinesh K.
, p. 1093 - 1100 (2018/02/22)
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.
Synthesis of 5-Aryl-3(2 H)-furanones Using Intramolecular Cyclization of Sulfonium Salts
Inagaki, Sho,Saito, Kai,Suto, Soichiro,Aihara, Hiromi,Sugawara, Aoi,Tamura, Satoru,Kawano, Tomikazu
, p. 13834 - 13846 (2018/11/23)
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.
Cationic gold(I)-catalyzed intramolecular cyclization of γ-hydroxyalkynones into 3(2H)-furanones
Egi, Masahiro,Azechi, Kenji,Saneto, Moriaki,Shimizu, Kaori,Akai, Shuji
supporting information; experimental part, p. 2123 - 2126 (2010/06/12)
"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
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
Binder, Joerg T.,Crone, Benedikt,Kirsch, Stefan F.,Liebert, Clemence,Menz, Helge
, p. 1636 - 1647 (2008/02/06)
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
Pd(II)-catalyzed cascade Wacker-Heck reaction: Chemoselective coupling of two electron-deficient reactants
Silva, Franck,Reiter, Maud,Mills-Webb, Rebecca,Sawicki, Marcin,Klaer, Daniel,Bensel, Nicolas,Wagner, Alain,Gouverneur, Veronique
, p. 8390 - 8394 (2007/10/03)
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.
Synthesis of acetylenic ketones by a Pd-catalyzed carbonylative three-component coupling reaction in [bmim]PF6
Fukuyama, Takahide,Yamaura, Ryo,Ryu, Ilhyong
, p. 711 - 715 (2007/10/03)
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.
Palladium-catalyzed oxidative cyclizations: Synthesis of dihydropyranones and furanones
Reiter, Maud,Turner, Hazel,Mills-Webb, Rebecca,Gouverneur, Veronique
, p. 8478 - 8485 (2007/10/03)
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
