- Preparation method of [alpha]-oxo-2-furanacetic acid
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The invention belongs to the field of preparation of organic compounds, and particularly relates to a preparation method of [alpha]-oxo-2-furanacetic acid, which comprises the following steps: 1) preparing oxalic acid and an organic alkali solution, controlling the temperature to 5-10 DEG C, dropwisely adding a trichloromethyl carbonate solution into the oxalic acid and organic alkali solution, and keeping the temperature for 2-4 hours until the solid is completely dissolved to obtain a solution A; obtaining a first solution; 2) preparing a furan and Lewis acid solution, controlling the temperature to be 20-25 DEG C, then dropwise adding the first solution into the furan and Lewis acid solution, and carrying out heat preservation for 1-2 hours to obtain a second solution; and 3) quenching the second solution at 0-10 DEG C to obtain the [alpha]-oxo-2-furanacetic acid. The preparation method disclosed by the invention does not generate nitric oxide and composite salt, and is low in treatment difficulty, low in environmental harm, low in temperature required by the whole reaction, low in energy consumption, simple in reaction step and short in time consumption.
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Paragraph 0032; 0034; 0042; 0044; 0050; 0052
(2021/05/01)
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- Fluorogenic Enzyme-Triggered Domino Reactions Producing Quinoxalin-2(1 H)-one-based Heterocycles
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A simple and effective biocompatible domino reaction triggered by a model protease and leading to the formation of strongly fluorescent quinoxalin-2(1H)-one N-heterocycles is described. Some positive attributes including versatility and the ability to pro
- Bonnin, Quentin,Chevalier, Arnaud,Dejouy, Garance,Michaudet, Cédric,Picquet, Michel,Renault, Kévin,Romieu, Anthony,Valverde, Ibai E.
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supporting information
p. 6494 - 6499
(2020/09/02)
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- Enantioselective Construction of 3-Hydroxypiperidine Scaffolds by Sequential Action of Light and Rhodium upon N-Allylglyoxylamides
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3-Hydroxypiperidine scaffolds were enantioselectively constructed in an atom-economical way by sequential action of light and rhodium upon N-allylglyoxylamides. In a formal sense, the allylic C-H bond was selectively cleaved and enantioselectively added a
- Ishida, Naoki,Ne?as, David,Masuda, Yusuke,Murakami, Masahiro
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supporting information
p. 7418 - 7421
(2015/06/30)
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- A new synthesis of versatile indolyl-3-carbonylnitriles
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Abstract Indolyl-3-carbonylnitriles are compounds with demonstrated utility as intermediates in organic chemistry. However, their synthesis remains a challenge, requiring the use of toxic sources of cyanide, and often proceeding in low yields. Accordingly, presented here is a new synthesis of these versatile reactants, via dehydration of easily accessible α-oxoacetamides in generally high yields under simple reaction conditions.
- Veale, Clinton G.L.
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p. 5287 - 5290
(2015/08/26)
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- Asymmetric friedel-crafts alkylation of α-substituted β-nitroacrylates: Access to β2,2-amino acids bearing indolic all-carbon quaternary stereocenters
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A highly enantioselective Friedel-Crafts alkylation reaction of indoles with acyclic α-substituted β-nitroacrylates is developed under the catalysis of Ni(ClO4)2-bisoxazoline complex at 1 mol % catalyst loading, affording chiral indolic β-nitroesters bearing all-carbon quaternary stereocenters in excellent yields and ees of up to 97%. Transformation of one of the products to β2,2-amino ester and tetrahydro-β-carboline through nitro reduction and sequential Pictet-Spengler cyclization was exemplified.
- Weng, Jian-Quan,Deng, Qiao-Man,Wu, Liang,Xu, Kai,Wu, Hao,Liu, Ren-Rong,Gao, Jian-Rong,Jia, Yi-Xia
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supporting information
p. 776 - 779
(2014/03/21)
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- Solvatochromic fluorescent 2-substituted 3-ethynyl quinoxalines: Four-component synthesis, photophysical properties, and electronic structure
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2-Substituted 3-ethynylquinoxalines can be rapidly synthesized in generally excellent yields by a consecutive four-component synthesis starting from electron-rich π-nucleophiles, oxalyl chloride, terminal alkynes, and 1,2-diaminoarenes. The title compound
- Gers, Charlotte F.,Nordmann, Jan,Kumru, Ceyda,Frank, Walter,Müller, Thomas J. J.
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p. 3296 - 3310
(2014/05/06)
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- Catalytic syntheses of N-heterocyclic ynones and ynediones by in situ activation of carboxylic acids with oxalyl chloride
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Breaking the bottleneck: α-Keto carboxylic acids and N-heterocyclic carboxylic acids are activated in situ with oxalyl chloride then catalytically alkynylated to give ynediones and N-heterocyclic ynones efficiently in a one-pot fashion. 5-Acylpyrazoles and 2-phenylaminopyrimidines, potentially interesting for pharmaceutical applications, are readily synthesized in concise one-pot, three-component syntheses. Copyright
- Boersch, Christina,Merkul, Eugen,Mueller, Thomas J. J.
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supporting information; experimental part
p. 10448 - 10452
(2011/12/05)
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- An investigation of structure-reactivity relationships of δ-alkenyl oximes; Competitive thermal reactions leading to cyclic nitrones and/or N-unsubstituted bicyclic isoxazolidines
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Thermal reactions of C-aryl δ-alkenyl oximes give N-unsubstituted bicylic lactone, lactam and pyrrolidine fused isoxazolidines by an intramolecular oxime olefin cycloaddition pathway (IOOC) and/or cyclic nitrones by an azaprotio cyclotransfer (APT) route; a number of factors, including the nature of the aryl group, the oxime geometry and the structure of the linker between the oxime and the terminal alkene, contribute to the competition. The nature of the aryl group, oxime geometry, and the structure of the linker between the oxime and the alkene influence the reactivity of C-aryl δ-alkenyl oximes.
- Doyle, Linda,Heaney, Frances
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experimental part
p. 7041 - 7049
(2010/10/18)
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- Electro-organic synthesis 68.1 diastereoselective cathodic reduction of phenylglyoxylic acid attached to chiral auxiliaries
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Two chiral auxiliaries were attached to phenylglyoxylic acid as amides in 67-70% yield. Cyclic voltammetry of one amide in acetonitrile-pivalic acid (0.117 mol 1-1) shows that it is irreversibly reduced at -0.73 to -1.07 V (vs. Ag/AgCl) dependi
- Reufer, Christian,Zielinski, Claudia,Schaefer, Hans Juergen,Froehlich, Roland
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p. 1023 - 1037
(2007/10/03)
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