2835-78-1Relevant articles and documents
Preparation of m-acylaniline derivatives by the reaction of tricarbonyl(cyclohexadienone O-benzyloxime)iron complex and higher order cuprates
Ban, Soo Ho,Hayashi, Yujiro,Narasaka, Koichi
, p. 393 - 394 (1998)
Reaction of tricarbonyl[(2,3,4,5-η)-2,4-cyclohexadien-1-one O-benzyloxime]iron and organocuprates, followed by the treatment with acetic anhydride and carbon monoxide, affords [(1,2,3,4-η)-1-(N-acetoxy-N-benzyloxyamino)-5-endo-acyl-1,3-cyclohexadiene] tri
Sodium Methyl Carbonate as an Effective C1 Synthon. Synthesis of Carboxylic Acids, Benzophenones, and Unsymmetrical Ketones
Hurst, Timothy E.,Deichert, Julie A.,Kapeniak, Lucas,Lee, Roland,Harris, Jesse,Jessop, Philip G.,Snieckus, Victor
supporting information, p. 3882 - 3885 (2019/06/07)
Reported is the synthesis of carboxylic acids, symmetrical ketones, and unsymmetrical ketones with selectivity achieved by exploiting the differential reactivity of sodium methyl carbonate with Grignard and organolithium reagents.
Chemoselective generation of acyl phosphates, acylium ion equivalents, from carboxylic acids and an organophosphate ester in the presence of a Br?nsted acid
Sumita, Akinari,Otani, Yuko,Ohwada, Tomohiko
supporting information, p. 1482 - 1485 (2017/02/05)
We describe the chemoselective conversion of carboxylic acids to functional aromatic ketones promoted by a tailored organophosphate ester in the presence of a Br?nsted acid. The protonated phosphate ester reacts with the carboxylic acid to form acyl phosphate, which reacts with benzenes to give aromatic ketones, probably through the acylium ion or its equivalent. The reaction time is short even at room temperature, and the reaction is compatible with various other functional groups, including amines, olefins, esters, amides and nitriles.
Carbonylative coupling of aryl tosylates/triflates with arylboronic acids under CO atmosphere
Hao, Cheng Yi,Wang, Dan,Li, Ya Wei,Dong, Lin Lin,Jin, Ying,Zhang, Xiu Rong,Zhu, He Yun,Chang, Sheng
, p. 86502 - 86509 (2016/09/23)
The carbonylative Suzuki-Miyaura reaction between aryl tosylates/triflates with arylboronic acid is herein reported, using base-free conditions and a balloon pressure of carbon monoxide. Under these conditions, unsymmetrical biaryl ketones were obtained in modest to excellent yields. This method was adapted to the synthesis of oxybenzone and ketoprofen in good yields under mild conditions.
Carbonylative Suzuki coupling reactions of aryl iodides with arylboronic acids over Pd/SiC
Cui, Yanli,Guo, Xiaoning,Wang, Yingyong,Guo, Xiangyun
, p. 322 - 327 (2015/09/28)
High surface area SiC has been used to prepare a Pd/SiC catalyst using the liquid reduction method, and the resulting catalyst was used for the carbonylative Suzuki coupling reaction of aryl iodides with arylboronic acids. The catalyst was also characterized by X-ray diffraction, inductively coupled plasma-mass spectroscopy and high-resolution transmission electron microscopy. The results of these analyses showed that homogeneous Pd nanoparticles with a mean diameter of 2.8 nm were uniformly dispersed on the SiC surface. Optimization of the reaction conditions for the carbonylative Suzuki coupling reaction, including the solvent, base, pressure, temperature and reaction time, revealed that the model reaction of iodobenzene (1.0 mmol) with phenylboronic acid (1.5 mmol) could reach 90% conversion with a selectivity of 99% towards the diphenyl ketone using 3 wt% Pd/SiC under 1.0 MPa of CO pressure at 100 °C for 8 h with K2CO3 (3.0 mmol) as the base and anisole as the solvent. The Pd/SiC catalyst exhibited broad substrate scope towards the carbonylative Suzuki coupling reaction of aryl iodides with arylboronic acids bearing a variety of different substituents. Furthermore, the Pd/SiC catalyst exhibited good recyclability properties and could be recovered and reused up to five times with the conversion of iodobenzene decreasing only slightly from 90% to 76%. The decrease in the catalytic activity after five rounds was attributed to the loss of active Pd during the organic reaction.
Silver-catalyzed decarboxylative acylation of arylglyoxylic acids with arylboronic acids
Cheng, Kai,Zhao, Baoli,Qi, Chenze
, p. 48698 - 48702 (2014/12/10)
The silver-catalyzed coupling of arylboronic acids with arylglyoxylic acids was found to be an extremely efficient route for the synthesis of unsymmetrical diaryl ketones. It can be conducted on a gram scale under mild and open-flask conditions with good functional group compatibility, avoiding the addition of expensive and/or toxic metals. This journal is
D-Glucosamine as a green ligand for copper catalyzed synthesis of primary aryl amines from aryl halides and ammonia
Thakur, Krishna Gopal,Ganapathy, Dhandapani,Sekar, Govindasamy
supporting information; experimental part, p. 5076 - 5078 (2011/06/10)
Replacing conventional reagents with environment friendly reagents is one of the primary goals of modern synthetic methodology and in this very primitive study about utilizing green, naturally available carbohydrate molecules as ligands in transition metal catalyzed reactions, we report Cu/d-glucosamine as an efficient catalyst for aniline synthesis.
Discovery of new cholesteryl ester transfer protein inhibitors via ligand-based pharmacophore modeling and QSAR analysis followed by synthetic exploration
Abu Khalaf, Reema,Abu Sheikha, Ghassan,Bustanji, Yasser,Taha, Mutasem O.
experimental part, p. 1598 - 1617 (2010/06/12)
Cholesteryl ester transfer protein (CETP) is involved in trafficking lipoprotein particles and neutral lipids between HDL and LDL and therefore is considered a valid target for treating dyslipidemic conditions and complications. Pharmacophore modeling and quantitative structure-activity relationship (QSAR) analysis were combined to explore the structural requirments for potent CETP inhibitors. Two pharmacophores emerged in the optimal QSAR equation (r2 = 0.800, n = 96, F = 72.1, r2LOO = 0.775, r2PRESS against 22 external test inhibitors = 0.707) suggesting the existence of at least two distinct binding modes accessible to ligands within CETP binding pocket. The successful pharmacophores were complemented with strict shape constraints in an attempt to optimize their receiver-operating characteristic (ROC) curve profiles. The validity of our modeling approach was experimentally established by the identification of several CETP inhibitory leads retrieved via in silico screening of the National Cancer Institute (NCI) list of compounds and an in house built database of drugs and agrochemicals. Two hits illustrated low micromolar IC50 values: NSC 40331 (IC50 = 6.5 μM) and NSC 89508 (IC50 = 1.9 μM). Active hits were then used to guide synthetic exploration of a new series of CETP inhibitors.
An enantiopure galactose oxidase model: synthesis of chiral amino alcohols through oxidative kinetic resolution catalyzed by a chiral copper complex
Mannam, Sreedevi,Sekar, Govindasamy
experimental part, p. 497 - 502 (2009/07/18)
An enantiopure galactose oxidase (GO) enzyme model has been synthesized from readily available (R)-BINAM and Cu(OTf)2, and the enantiopure GO model has been effectively used in situ as an efficient chiral catalyst for the synthesis of chiral amino alcohols through oxidative kinetic resolution (OKR), where molecular oxygen is used as the sole oxidant. Under the proposed catalytic conditions, both ortho- and para-substituted amino alcohols were resolved with good to excellent enantiomeric excesses through oxidative kinetic resolution.
Efficient one-pot Friedel-Crafts acylation of benzene and its derivatives with unprotected aminocarboxylic acids in polyphosphoric acid
Ivanov, Iliyan,Nikolova, Stoyanka,Statkova-Abeghe, Stela
, p. 1405 - 1411 (2007/10/03)
A number of aminobenzophenones have been synthesized by acylation of benzene and its derivatives with different 2-,3-,4-aminobenzoic and 4-aminophenyl-acetic acids in polyphosphoric acid via Friedel-Crafts reaction as compounds with expected antitumor activity. Copyright Taylor & Francis Group, LLC.
