- Reaction of substituted phenols and alcohols with (E)-1-chloro-3,3,3-trifluoropropene (HFCO-1233zd)
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Simple and convenient one-pot procedures for the preparation of ArOCH=CHCF3, ROCH=CHCF3 and CF3CH=CHOArOCH = CHCF3 starting from the industrial product HFCO-1233zd (CF3CH=CHCl) are presented. These syntheses involve the reaction of 1233zd with phenols and alcohols in the presence of potassium hydroxide in DMF or pyridine solvent at elevated temperatures.
- Filatov, Andrey A.,Kremlev, Mikhail M.,Mushta, Oleksii ?.,Yagupolskii, Yurii L.
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- Electrochemical esterification reaction of alkynes with diols: Via cleavage of carbon-carbon triple bonds without catalyst and oxidant
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A novel electrochemical esterification of alkynes for the synthesis of esters was developed in which diols and their derivatives were used as the partners. This method is green as it is catalyst-free, oxidant-free, and additive-free and shows atom-economy. This is the first example of an electrochemical reaction via cleavage of carbon-carbon triple bonds. Meanwhile, this is also the first example of a carbon-carbon triple bond cleavage reaction of alkynes with diols. This journal is
- Cheng, Hui-Hui,Gao, Hui,Li, Pin-Hua,Shen, Hui-Zhi,Wang, Pei-Long
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supporting information
p. 6783 - 6791
(2020/11/09)
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- Protecting-group-free synthesis of hydroxyesters from amino alcohols
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The synthesis of hydroxyesters from carboxylic acids and unprotected amino alcohols in both continuous flow and batch processes is reported. The formation of a transient diazonium species with a dinitrite reagent is key in this transformation. The reaction conditions are compatible with a variety of functional groups.
- Joseph-Valcin, Eve-Marline,Lebel, Hélène,Reynard, Guillaume
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supporting information
p. 10938 - 10941
(2020/10/02)
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- METHOD FOR PREPARING BENZOIC ACID ESTERS
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The invention relates to the method of preparing benzoic acid esters which provides high selectivity of the process, and high yield of the desired product, as well as the reduction of the duration of the esterification process, comprising esterification of benzoic acid with monohydric alcohols having a number of carbon atoms from 6 to 12, or polyhydric alcohols having a number of carbon atoms from 2 to 10, in the presence of metal containing catalyst in the media of aromatic solvent at the stepwise buildup of the temperature of the process to 180-200°C, further to 200-220°C, and then to 240-250°C.
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Page/Page column 14; 15; 16; 17; 18; 19; 20;
(2019/04/16)
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- Domino Two-Step Oxidation of β-Alkoxy Alcohols to Hemiacetal Esters: Linking a Stoichiometric Step to an Organocatalytic Step with a Common Organic Oxidant
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Primary and secondary β-alkoxy alcohols can be cleanly and efficiently oxidized into hemiacetal esters in a cascade two-step process. mCPBA serves both as a stoichiometric oxidant in the first TEMPO-catalyzed step, converting alcohols to aldehydes/ketones, and as a reagent in the second Baeyer–Villiger stoichiometric oxidation, transforming the aldehydes/ketones into hemiacetal esters. The use of an oxidant common to both steps enables the domino reaction to proceed under a single experimental setting. Longer oxidative cascade sequences are possible when this new methodology is applied to suitable substrates.
- Targel, Tom,Ramesh, Palakuri,Portnoy, Moshe
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supporting information
p. 3017 - 3021
(2018/06/27)
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- Graphene Oxide: An Efficient Acid Catalyst for the Construction of Esters from Acids and Alcohols
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Graphene oxide was found to be an efficient and reusable acid catalyst for the esterification reaction. A wide range of aliphatic and aromatic acids and alcohols were compatible with the standard conditions and afforded the corresponding products in good yields. The heterogeneous catalyst can be easily recovered and recycled in dichloro-ethane solvent with good catalytic activity.
- Chen, Zhengwang,Wen, Yuelu,Fu, Yejuan,Chen, Hai,Ye, Min,Luo, Guotian
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supporting information
p. 981 - 985
(2017/05/05)
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- Rate-acceleration in gold-nanocluster-catalyzed aerobic oxidative esterification using 1,2- and 1,3-diols and their derivatives
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Aerobic oxidation of aldehydes to 1,2- and 1,3-diol monoesters was catalyzed by polymer-incarcerated gold nanoclusters under ambient conditions. The esterification proceeded much faster with 1,2- and 1,3-diols and their derivatives rather than with methanol. Magnum PI: Gold-nanocluster catalysts, PI-Au, that were immobilized on polystyrene-based polymers with cross-linking moieties, were used to catalyze the syntheses of 1,2 and 1,3-diol monoesters and their derivatives from aldehydes. The effect of neighboring-group participation in the esterification reaction is also described. Copyright
- Yasukawa, Tomohiro,Miyamura, Hiroyuki,Kobayashi, Shu
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experimental part
p. 621 - 627
(2011/10/12)
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- The in vitro transport of model thiodipeptide prodrugs designed to target the intestinal oligopeptide transporter, PepT1
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A thiodipeptide carrier system is shown to be effective at enabling a range of covalently bound molecules, including benzyl, benzoyl and ibuprofen conjugates, to be transported via the intestinal peptide transporter PepT1, demonstrating its potential as a rational drug delivery target.
- Foley, David,Pieri, Myrtani,Pettecrew, Rachel,Price, Richard,Miles, Stephen,Lam, Ho Kam,Bailey, Patrick,Meredith, David
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supporting information; experimental part
p. 3652 - 3656
(2009/10/23)
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- FUSED HETEROCYCLIC COMPOUND
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The present invention relates to a compound represented by the formula: wherein W is C(R 1 ) or N, each A is an optionally substituted aryl group or a heteroaryl group, X 1 is -NR 3 -Y 1 -, -O-, -S-, -SO-, -SO 2 or -CHR 3 - wherein R 3 is a hydrogen atom or an optionally substituted aliphatic hydrocarbon group, or R 3 is optionally bonded to A to form an optionally substituted ring structure, R 1 is a hydrogen atom or an optionally substituted group bonded via a carbon atom, a nitrogen atom or an oxygen atom, R 2 is a hydrogen atom or optionally substituted group bonded via a carbon atom or a sulfur atom, or R 1 and R 2 , or R 2 and R 3 are optionally bonded to form an optionally substituted ring structure, or a salt thereof, and a tyrosine kinase inhibitor or an agent for the prophylaxis or treatment of cancer, which contains this compound or a prodrug thereof.
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Page/Page column 179-180
(2008/06/13)
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- Kinetic stabilization of an oligomeric protein by a single ligand binding event
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Protein native state stabilization imposed by small molecule binding is an attractive strategy to prevent the misfolding and misassembly processes associated with amyloid diseases. Transthyretin (TTR) amyloidogenesis requires rate-limiting tetramer dissociation before misassembly of a partially denatured monomer ensues. Selective stabilization of the native TTR tetramer over the dissociative transition state by small molecule binding to both thyroxine binding sites raises the kinetic barrier of tetramer dissociation, preventing amyloidogenesis. Assessing the amyloidogenicity of a TTR tetramer having only one amyloidogenesis inhibitor (I) bound is challenging because the two small molecule binding constants are generally not distinct enough to allow for the exclusive formation of TTR·I in solution to the exclusion of TTR·I2 and unliganded TTR. Herein, we report a method to tether one fibril formation inhibitor to TTR by disulfide bond formation. Occupancy of only one of the two thyroxine binding sites is sufficient to inhibit tetramer dissociation in 6.0 M urea and amyloidogenesis under acidic conditions by imposing kinetic stabilization on the entire tetramer. The sufficiency of single occupancy for stabilizing the native state of TTR provides the incentive to search for compounds displaying striking negative binding cooperativity (e.g., Kd1 in nanomolar range and Kd2 in the micromolar to millimolar range), enabling lower doses of inhibitor to be employed in the clinic, mitigating potential side effects.
- Wiseman, R. Luke,Johnson, Steven M.,Kelker, Matthew S.,Foss, Ted,Wilson, Ian A.,Kelly, Jeffery W.
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p. 5540 - 5551
(2007/10/03)
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- Al2O3/MeSO3H (AMA) as a new reagent with high selective ability for monoesterification of diols
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A new facile method for monoesterification of diols has been developed. A variety of diols, in particular oligoethylene glycols, were selectively monoesterified in excellent yields by reaction with aromatic and aliphatic acids in the presence of Al2O3/MeSO3H as a new reagent without use of any solvents.
- Sharghi, Hashem,Sarvari, Mona Hosseini
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p. 3627 - 3633
(2007/10/03)
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- Highly selective methodology for the direct conversion of aromatic aldehydes to glycol monoesters
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Al2O3/MeSO3H (AMA) was found to be an extremely efficient reagent for the conversion of aromatic aldehydes and diols to glycol monoesters. The remarkable selectivity achieved with this reagent is an attractive feature of t
- Sharghi, Hashem,Sarvari, Mona Hosseini
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p. 4096 - 4099
(2007/10/03)
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- Peroxovanadium-catalyzed oxidative esterification of aldehydes
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The peroxovanadium species generated from V2O5 and hydrogen peroxide, which is liberated from peroxy salts such as sodium perborate (SPB) or sodium percarbonate (SPC), transform aldehydes directly into esters in an alcoholic medium. Monoesters of diols have been achieved directly in one pot from aldehydes. High catalytic turnover number combined with inexpensive, easily available reagents and innocuous side products from the reaction make it a suitable alternative for the synthesis of esters from aldehydes.
- Gopinath, Rangam,Barkakaty, Balaka,Talukdar, Bandana,Patel, Bhisma K.
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p. 2944 - 2947
(2007/10/03)
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- Tetrabutylammonium tribromide (TBATB)-promoted tetrahydropyranylation/depyranylation of alcohols
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Alcohols are tetrahydropyranylated rapidly in high yields in the presence of a catalytic amount of TBATB in dichloromethane at room temperature. Depyranylation to their parent alcohol is achieved in quantitative yields by merely changing the solvent to methanol.
- Naik, Sarala,Gopinath, Rangam,Patel, Bhisma K
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p. 7679 - 7681
(2007/10/03)
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- Deacylation of Pyrrole and other Aromatic Ketones
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Ethyl 4-acetyl-3,5-dimethyl-1H-pyrrole-2-carboxylate (1a) reacts rapidly with ethylene glycol in refluxing benzene with p-toluenesulfonic acid or perchloric acid as a catalyst to give ethyl 3,5-dimethyl-1H-pyrrole-2-carboxylate (3) in high yield (96 percent).Various 2- and 3-acylpyrroles can be efficiently deacylated by using this procedure.Other ketones which undergo deacylation include phenyl(2-phenylindol-3-yl)methanone (19), 1-(5-methyl-1-phenylpyrazol-4-yl)ethanone (20), and 2,4-dimethoxybenzophenone.Certain pyrrole ketones where the acyl group is flanked by two ring methyl groups are also cleaved under acidic conditions by using ethanedithiol.
- Moon, M. W.,Wade, R. A.
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p. 2663 - 2669
(2007/10/02)
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