- A CO2-mediated base catalysis approach for the hydration of triple bonds in ionic liquids
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Herein, we report a CO2-mediated base catalysis approach for the activation of triple bonds in ionic liquids (ILs) with anions that can chemically capture CO2 (e.g., azolate, phenolate, and acetate), which can achieve hydration of triple bonds to carbonyl chemicals. It is discovered that the anion-complexed CO2 could abstract one proton from proton resources (e.g., IL cation) and transfer it to the CN or CC bonds via a six-membered ring transition state, thus realizing their hydration. In particular, tetrabutylphosphonium 2-hydroxypyridine shows high efficiency for hydration of nitriles and CC bond-containing compounds under a CO2 atmosphere, affording a series of carbonyl compounds in excellent yields. This catalytic protocol is simple, green, and highly efficient and opens a new way to access carbonyl compounds via triple bond hydration under mild and metal-free conditions.
- Han, Buxing,Ke, Zhengang,Li, Ruipeng,Liu, Zhimin,Tang, Minhao,Wang, Yuepeng,Zeng, Wei,Zhang, Fengtao,Zhao, Yanfei
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supporting information
p. 9870 - 9875
(2021/12/27)
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- Ti-superoxide catalyzed oxidative amidation of aldehydes with saccharin as nitrogen source: Synthesis of primary amides
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A new heterogeneous catalytic system (Ti-superoxide/saccharin/TBHP) has been developed that efficiently catalyzes oxidative amidation of aldehydes to produce various primary amides. The protocol employs saccharin as amine source and was found to tolerate a wide range of substrates with different functional groups. Moderate to excellent yields, catalyst reusability and operational simplicity are the main highlights. A possible mechanism and the role of the catalyst in oxidative amidation have also been discussed.
- Kamble, Rohit B.,Mane, Kishor D.,Rupanawar, Bapurao D.,Korekar, Pranjal,Sudalai,Suryavanshi, Gurunath
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p. 724 - 728
(2020/01/23)
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- Production method of p-hydroxyphenylacetamide
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The invention relates to a production method of p-hydroxyphenylacetamide and belongs to the medicine field. Phenol and glyoxylic acid are taken as raw materials to be prepared into a competitive product via processes of synthesis, reduction and ammonolysis. The production method has the advantages that the optimal synthesis process is determined, yield of the obtained p-hydroxyphenylacetamide can reach over 80%, purity can reach more than 99%, and the technical process is simpler, easy to implement and environment friendly.
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- Synthesis and PGE2 production inhibition of 1H-furan-2,5-dione and 1H-pyrrole-2,5-dione derivatives
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3,4-Diphenyl-substituted 1H-furan-2,5-dione and 1H-pyrrole-2,5-dione derivatives were synthesized and evaluated for the inhibitory activities on LPS-induced PGE2 production in RAW 264.7 macrophage cells. Both 1H-furan-2,5-dione and 1H-pyrrole-2,5-dione rings as main scaffolds were easily obtained using one of three synthetic methods. Among the compounds investigated, 1H-3-(4-sulfamoylphenyl)-4-phenyl-pyrrole-2,5-dione (6l) showed a strong inhibitory activity (IC50 = 0.61 μM) of PGE2 production.
- Moon, Jong Taik,Jeon, Ji Young,Park, Hang Ah,Noh, Young-Soo,Lee, Kyung-Tae,Kim, Jungahn,Choo, Dong Joon,Lee, Jae Yeol
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scheme or table
p. 734 - 737
(2010/06/22)
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- Isolation and production of catalytic antibodies using phage technology
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Disclosed and claimed are methods for producing catalytic antibodies, including human catalytic antibodies, from bacteriophage. The methods require the cloning, selection, screening, and isolation of catalytic antibodies. Also disclosed and claimed are the products themselves, the catalytic antibodies, made from the phage technology. In addition, catalytic antibodies produced from the phage technology and useful in prodrug activation are disclosed and claimed. And finally, the invention also understands the production of catalytic antibodies to phosphonates.
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- A synthesis of atenolol using a nitrile hydration catalyst
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The synthesis of atenolol is described using a platinum containing homogeneous catalyst for the conversion of a nitrile to an amide. The catalytic reaction may be employed as the final step in the synthesis or in the preparation of the intermediate 4-hydroxyphenylacetamide. The structure of the nitrile intermediate, 1-(4′-cyanomethylphenoxy)-2-hydroxy-3-isopropylaminopropane, has been determined by X-ray crystallography.
- Akisanya, Joseph,Parkins, Adrian W.,Steed, Jonathan W.
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p. 274 - 276
(2013/09/08)
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- Facile 1,2-aryl migration of 2-halomethyl-2-(4'-hydroxyphenyl) ketals: A novel single step synthesis of 4-hydroxyphenylacetic acid and its derivatives
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1,2-Aryl migration of 1-halomethyl-2-(4-hydroxyphenyl) ketals, obtained from 2-bromomethyl 4-hydroxyacetophenone, under mild basic conditions have been shown to give 4-hydroxyphenylacetic acid or its derivatives which are key intermediates in the preparation of Atenolol, a well known cardiac β-blocker.
- Kumar, Ashok,Rane, Ramkrishna A.,Ravindran, Vaikyparambil K.,Dike, Suneel Y.
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p. 1133 - 1141
(2007/10/03)
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- Electronic Substituent Effects in the Nitrilase-Catalyzed Hydrolysis of Para-Substituted Benzyl Cyanides
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The initial rates of the nitrilase (Novo)-catalyzed hydrolysis of a series of para-substituted benzyl cyanides (R = NO2, Cl, OCH3, OH, NH2) were found to be susceptible to the nature of the para-substituent of the substrate and a Hammett-type linear free energy correlation was observed with ρ = 0.96.In a separate study, effective solubilization of substituted benzyl cyanide substrates having electron-donating groups (OH, NH2, OCH3) was achieved upon mixing with β-cyclodextrin to form 1:1 mol ratio inclusion complexes, but para-substituted benzyl cyanides with electron-withdrawing groups (Cl, NO2) were not fully solubilized under the same conditions.In addition, it was shown that the presence of β-cyclodextrin not only had no inhibitory effect on the enzyme activity, but it actually increased the initial rate of hydrolysis of the unsubstituted benzyl cyanide:β-cyclodextrin inclusion complex.However, the initial rates of hydrolysis were observed to be smaller when β-cyclodextrin was added to the para-substituted benzyl cyanides.
- Geresh, Shimona,Giron, Yakir,Gilboa, Ygal,Glaser, Robert
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p. 10099 - 10102
(2007/10/02)
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- Preparation of aromatic acetamides from aryl methyl ketones
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A method is provided for preparing aromatic acetamides comprising reacting an aryl methyl ketone containing the same number of carbon atoms as the aromatic acetamide, with sulfur and ammonia under substantially anhydrous conditions. The method is particularly useful for the preparation of 4-hydroxyphenylacetamide from 4-hydroxyacetophenone.
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- Process for producing p-hydroxyphenyl/acetic acid
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A process for the preparation of p-hydroxyphenylacetic acid by reducing p-hydroxymandelic acid with a stannous salt. The product is a valuable intermediate for the preparation of the β-adrenergic blocking agent atenolol.
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- Process for the manufacture of p-hydroxybenzyl cyanide
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A process for the manufacture of p-hydroxybenzyl cyanide which comprises reacting p-hydroxymandelic acid with cyanide ion. The product is a useful intermediate for the preparation of the β-adrenergic blocking agent atenolol.
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