- Photo-induced oxidative cleavage of C-C double bonds for the synthesis of biaryl methanoneviaCeCl3catalysis
-
A Ce-catalyzed strategy is developed to produce biaryl methanonesviaphotooxidative cleavage of C-C double bonds at room temperature. This reaction is performed under air and demonstrates high activity as well as functional group tolerance. A synergistic Ce/ROH catalytic mechanism is also proposed based on the experimental observations. This protocol should be the first successful Ce-catalyzed photooxidation reaction of olefins with air as the oxidant, which would provide inspiration for the development of novel Ce-catalyzed photochemical synthesis processes.
- Xie, Pan,Xue, Cheng,Du, Dongdong,Shi, SanShan
-
supporting information
p. 6781 - 6785
(2021/08/20)
-
- Chiral electron-rich PNP ligand with a phospholane motif: Structural features and application in asymmetric hydrogenation
-
Despite the remarkable reactivity that was achieved by a series of transition-metal catalysts with a PNP type ligand, the electron-rich chiral PNP ligands have still been rarely reported because of the difficulties in synthesis and the nature of air-sensitivity. Herein, we report a novel chiral PNP ligand (Heng-PNP) with both a rigid backbone and a bulky tert-butyl group on the phospholane motif. We successfully obtained its divalent iron complex. The chiral environment of its Ir(III) complex was also discussed with quadrant analysis. This tridentate ligand was applied in iridium-catalyzed asymmetric hydrogenation of challenging diaryl ketones: up to 98% ee and 500 TON are achieved. Computational study showed that the twist of conjugate aryl group in the substrate (induced by the special chiral pocket of Ir/Heng-PNP complex) leads to the energy difference in the enantiodetermining step.
- Wang, Heng,Zhang, Yao,Yang, Tilong,Guo, Xiaochong,Gong, Quan,Wen, Jialin,Zhang, Xumu
-
p. 8796 - 8801
(2020/11/13)
-
- Silylcarboxylic Acids as Bifunctional Reagents: Application in Palladium-Catalyzed External-CO-Free Carbonylative Cross-Coupling Reactions
-
A palladium-catalyzed external-CO-free carbonylative Hiyama-Denmark cross-coupling reaction is presented. The introduction of silylcarboxylic acids as bifunctional reagents (CO and nucleophile source) avoids the need for external gaseous CO and a silylarene coupling partner. The transformation features high functional group tolerance and it is successful with electron-rich, -neutral, and -poor aryl iodides. Stoichiometric studies and control experiments provide insight into the reaction mechanism and support the hypothesized dual role of silylcarboxylic acids. (Figure presented.).
- Li, Xiong,Xu, Jie,Li, Yue,Kramer, S?ren,Skrydstrup, Troels,Lian, Zhong
-
supporting information
p. 4078 - 4083
(2020/07/30)
-
- Kinetically Controlled, Highly Chemoselective Acylation of Functionalized Grignard Reagents with Amides by N?C Cleavage
-
The direct transition-metal-free acylation of amides with functionalized Grignard reagents by highly chemoselective N?C cleavage under kinetic control has been accomplished. The method offers rapid and convergent access to functionalized biaryl ketones through transient tetrahedral intermediates. The direct access to functionalized Grignard reagents by in situ halogen–magnesium exchange promoted by the versatile turbo-Grignard reagent (iPrMgCl?LiCl) permits excellent substrate scope with respect to both the amide and Grignard coupling partners. These reactions enable facile, operationally simple and chemoselective access to tetrahedral intermediates from amides under significantly milder conditions than chelation-controlled intermediates. This novel direct two-component coupling sets the stage for using amides as acylating reagents in an alternative paradigm to the metal-chelated approach, acyl metals and Weinreb amides.
- Li, Guangchen,Szostak, Michal
-
supporting information
p. 611 - 615
(2020/01/02)
-
- Arylation of Aldehydes to Directly Form Ketones via Tandem Nickel Catalysis
-
A nickel-catalyzed arylation of both aliphatic and aromatic aldehydes proceeds with air-stable (hetero)arylboronic acids, with an exceptionally wide substrate scope. The neutral condition tolerates acidic hydrogen and sensitive polar groups and also preserves α-stereocenters of some chiral aldehydes. Interestingly, this nickel(0) catalysis does not follow common 1,2-insertion of arylmetal species to aldehydes and β-hydrogen elimination.
- Lei, Chuanhu,Zhu, Daoyong,Tangcueco, Vicente Iii Tiu,Zhou, Jianrong Steve
-
supporting information
p. 5817 - 5822
(2019/08/26)
-
- Synthetic method of ketone compounds
-
The invention belongs to the field of organic synthesis, and particularly relates to a synthetic method of ketone compounds. The invention provides a synthetic method of the ketone compounds. In the presence of a silver catalyst and alkaline additive, hydrazine and carbonyl carboxylic acid are used as substrates to have oxidation reaction to generate the ketone compounds. In the synthetic method of the invention, the used substrates, catalyst and additive are easy to obtain, and the cost is low; meanwhile, the generated byproducts are nitrogen, water and carbon dioxide, so that the synthetic method is environmentally friendly, pollution-free, and capable of meeting the sustainable development concept; and thirdly, by adopting the preparation method, the pre-activation is not needed, the yield is greater than 60 percent or, and the synthetic efficiency is high; and the technical defects in the prior art that the synthesis method of the ketone compounds is complicated in synthetic procedures, high in catalyst price and difficult in synthesizing an active intermediate can be solved.
- -
-
Paragraph 0070-0074
(2018/11/22)
-
- Suzuki-Miyaura Cross-Coupling of N-Acylpyrroles and Pyrazoles: Planar, Electronically Activated Amides in Catalytic N-C Cleavage
-
The formation of C-C bonds from amides by catalytic activation of the amide bond has been thus far possible by steric distortion. Herein, we report the first example of a general Pd-catalyzed Suzuki-Miyaura cross-coupling of planar amides enabled by the combination of (i) electronic-activation of the amide nitrogen in N-acylpyrroles and pyrazoles and (ii) the use of a versatile Pd-NHC catalysis platform. The origin and selectivity of forming acylmetals, including the role of twist, are discussed.
- Meng, Guangrong,Szostak, Roman,Szostak, Michal
-
p. 3596 - 3599
(2017/07/15)
-
- Nickel-Catalyzed Negishi Cross-Coupling of N -Acylsuccinimides: Stable, Amide-Based, Twist-Controlled Acyl-Transfer Reagents via N-C Activation
-
This paper reports a room temperature, nickel-catalyzed Negishi cross-coupling of N -acylsuccinimides with arylzinc reagents via selective N-C bond cleavage enabled by amide bond twist. The reaction proceeds using a commercially available, air-stable Ni(II) precatalyst in the absence of additives under exceedingly mild conditions. Of broad interest, this report introduces N -acylsuccinimides as stable, crystalline, electrophilic, cost-effective, benign, amide-based acyl transfer reagents via acyl metal intermediates. The reaction selectivity is governed by half-twist of the amide bond in N -acylsuccinimides, thus opening the door for applications in metal-catalyzed manifolds via redox-neutral reaction pathways tuneable by amide bond distortion.
- Shi, Shicheng,Szostak, Michal
-
p. 3602 - 3608
(2017/08/15)
-
- N-Acylsuccinimides: Efficient acylative coupling reagents in palladium-catalyzed Suzuki coupling via C–N cleavage
-
An acylative Suzuki coupling of activated amides with aryl boronic acids has been reported via palladium-catalyzed C–N bond cleavage. This protocol demonstrate amides can be activated by an atom-economic and cheap succinimide, which can be efficiently utilized to synthesize broad array of diaryl ketones in moderate to good yields.
- Cui, Ming,Chen, Zeyu,Liu, Tingting,Wang, Hui,Zeng, Zhuo
-
p. 3819 - 3822
(2017/09/15)
-
- Ni-Catalyzed cross-coupling reactions of N-acylpyrrole-type amides with organoboron reagents
-
The catalytic conversion of amides to ketones is highly desirable yet challenging in organic synthesis. We herein report the first Ni/bis-NHC-catalyzed cross-coupling of N-acylpyrrole-type amides with arylboronic esters to obtain diarylketones. This method is facilitated by a new chelating bis-NHC ligand. The reaction tolerates diverse functional groups on both arylamide and arylboronic ester partners including sensitive ester and ketone groups.
- Huang, Pei-Qiang,Chen, Hang
-
p. 12584 - 12587
(2017/11/30)
-
- Light-Driven Enantioselective Organocatalytic β-Benzylation of Enals
-
A photochemical organocatalytic strategy for the direct enantioselective β-benzylation of α,β-unsaturated aldehydes is reported. The chemistry capitalizes upon the light-triggered enolization of 2-alkyl-benzophenones to afford hydroxy-o-quinodinomethanes. These fleeting intermediates are stereoselectively intercepted by chiral iminium ions, transiently formed upon condensation of a secondary amine catalyst with enals. Density functional theory (DFT) studies provided an explanation for why the reaction proceeds through an unconventional Michael-type addition manifold, instead of a classical cycloaddition mechanism and subsequent ring-opening.
- Dell'Amico, Luca,Fernández-Alvarez, Victor M.,Maseras, Feliu,Melchiorre, Paolo
-
p. 3304 - 3308
(2017/03/17)
-
- At normal pressure fragrant ketone copper catalytic synthesis method
-
The invention discloses a method of synthesizing diaryl ketone under normal pressure by virtue of copper catalysis. The method is as follows: in a solvent alcohol or aqueous liquor of alcohol, under action of alkali and acid, adding a copper catalyst, alkyl iodide, alkyl boric acid and carbon monoxide to directly carry out crossed coupling reaction to prepare diaryl ketone compounds. According to the invention, the method of preparing diaryl ketone compounds by carbonylation Suzuki coupling reaction has the advantages as follows: the catalyst is wide in source, cheap and small in toxicity; the reaction is free of ligand in reaction and good in activity; the reaction is carried out under the normal pressure and selectivity is high; a substrate source is wide and stable; functional group compatibility is good and scope of application for the substrate is wide; a reaction medium is environment-friendly and recyclable. Under the condition of optimizing reaction conditions, the target product separating yield is 95%.
- -
-
Paragraph 0032; 0033; 0038
(2017/07/14)
-
- At normal pressure fragrant ketone nickel catalytic synthesis method
-
The invention discloses a method for synthesizing diarylketone under the catalysis of nickel at normal pressure. The method comprises the steps of enabling aryl iodide, arylboronic acid and carbon monoxide to be subjected to direct cross-coupling reaction in a solvent polyethylene glycol or a water solution of polyethylene glycol under the catalysis of a nickel catalyst and the combined action of alkaline and acid at normal pressure to prepare a diarylketone compound. The method has the advantages of wide catalyst source, low price, little toxicity, reaction at normal pressure, high selectivity, no need of ligands in reaction, good activity, good functional group compatibility, wide substrate application range, wide substrate source, stable substrate, green and recyclable reaction medium and the like. The separation yield of target products is up to 93% under an optimized reaction condition.
- -
-
Paragraph 0003; 0017; 0027-0033
(2017/08/02)
-
- Iron-catalyzed carbonylation of aryl halides with arylborons using stoichiometric chloroform as the carbon monoxide source
-
A general iron-catalyzed carbonylative Suzuki-Miyaura coupling of aryl halides with arylborons is reported, using stoichiometric CHCl3 as the CO source. The high efficiency, economy, selectivity, and operational simplicity of this transformation make this method a valuable tool in organic synthesis. Importantly, the presented strategy allows effective 13C labeling simply by using the commercially available 13C-labeled CHCl3. On the basis of the initial mechanistic exploration, an aryl radical intermediate is proposed in the present carbonylation process.
- Zhao, Hongyuan,Du, Hongyan,Yuan, Xiaorong,Wang, Tianjiao,Han, Wei
-
supporting information
p. 5782 - 5787
(2016/11/06)
-
- Co(III)-Catalyzed Synthesis of Quinazolines via C-H Activation of N-Sulfinylimines and Benzimidates
-
C-H activation of arenes has been established as an important strategy for heterocycle synthesis via annulations between arenes and unsaturated coupling partners. However, nitriles failed to act as such a coupling partner. Dioxazolones have been employed as a synthon of nitriles, and subsequent coupling with arenes such as N-sulfinylimines and benzimidates bearing a functionalizable directing group provided facile access to two classes of quinazolines under Co(III)-catalysis.
- Wang, Fen,Wang, He,Wang, Qiang,Yu, Songjie,Li, Xingwei
-
supporting information
p. 1306 - 1309
(2016/04/01)
-
- Enantioselective Organocatalytic Diels-Alder Trapping of Photochemically Generated Hydroxy-o-Quinodimethanes
-
The photoenolization/Diels-Alder strategy offers straightforward access to synthetically valuable benzannulated carbocyclic products. This historical light-triggered process has never before succumbed to efforts to develop an enantioselective catalytic approach. Herein, we demonstrate how asymmetric organocatalysis provides simple yet effective catalytic tools to intercept photochemically generated hydroxy-o-quinodimethanes with high stereoselectivity. We used a chiral organic catalyst, derived from natural cinchona alkaloids, to activate maleimides toward highly stereoselective Diels-Alder reactions. An unconventional mechanism of stereocontrol is operative, wherein the organocatalyst is actively involved in both the photochemical pathway, by leveraging the formation of the reactive photoenol, and the stereoselectivity-defining event.
- Dell'amico, Luca,Vega-Pe?aloza, Alberto,Cuadros, Sara,Melchiorre, Paolo
-
p. 3313 - 3317
(2016/03/22)
-
- Light-Driven Carboxylation of o-Alkylphenyl Ketones with CO2
-
o-Alkylphenyl ketones undergo a C-C bond forming carboxylation reaction with CO2 simply upon irradiation with UV light or even solar light. The reaction presents a clean process exploiting light energy as the driving force for carboxylation of organic molecules with CO2.
- Masuda, Yusuke,Ishida, Naoki,Murakami, Masahiro
-
supporting information
p. 14063 - 14066
(2015/11/25)
-
- Synthesis of ketones via organolithium addition to acid chlorides using continuous flow chemistry
-
An efficient method for the synthesis of ketones using organolithium and acid chlorides under continuous flow conditions has been developed. In contrast to standard batch chemistry, over-addition of the organolithium to the ketone for the formation of the undesired tertiary alcohol has been minimised representing a direct approach toward ketones.
- Moon, Soo-Yeon,Jung, Seo-Hee,Bin Kim,Kim, Won-Suk
-
p. 79385 - 79390
(2015/10/06)
-
- Erbium trifluoromethanesulfonate catalyzed Friedel-Crafts acylation using aromatic carboxylic acids as acylating agents under monomode-microwave irradiation
-
Erbium trifluoromethanesulfonate is found to be a good catalyst for the Friedel-Crafts acylation of arenes containing electron-donating substituents using aromatic carboxylic acids as the acylating agents under microwave irradiation. An effective, rapid and waste-free method allows the preparation of a wide range of aryl ketones in good yields and in short reaction times with minimum amounts of waste.
- Tran, Phuong Hoang,Hansen, Poul Erik,Nguyen, Hai Truong,Le, Thach Ngoc
-
p. 612 - 618
(2015/02/19)
-
- Experimental and DFT study on the indium-mediated synthesis of benzophenones via arylstannanes
-
Experimental results of the solvent-free, indium-promoted reaction of aroyl chlorides with arylstannanes showed a narrow scope; its efficiency depends both on the extent of methylation in the latter and on the nature, number and position of the substituents in the former. With the purpose of explaining experimental results, a theoretical analysis with DFT methods was performed for a set of selected cases. This journal is
- Lo Fiego, Marcos J.,Dorn, Viviana B.,Badajoz, Mercedes A.,Lockhart, Mara T.,Chopa, Alicia B.
-
p. 49079 - 49085
(2014/12/10)
-
- One-pot synthesis of diarylmethanones through palladium-catalyzed sequential coupling and aerobic oxidation of aryl bromides with acetophenone as a latent carbonyl donor
-
A one-pot palladium-catalyzed synthesis of symmetrical and unsymmetrical diarylmethanones using acetophenone and aryl bromides as raw materials has been developed. In this reaction, acetophenone acts as a latent carbonyl donor and two pathways of palladium-catalyzed sequential coupling and aerobic oxidation are identified. The reaction is applicable to a spectrum of substrates and delivers the products in moderate to good yields. This method can be used for the synthesis of ketoprofen, a nonsteroidal anti-inflammatory drug, in a two-step procedure and 45% overall yield.
- Wang, Xing,Liu, Fu-Di,Tu, Hai-Yang,Zhang, Ai-Dong
-
p. 6554 - 6562
(2014/08/05)
-
- Iron-catalyzed carbonylative Suzuki reactions under atmospheric pressure of carbon monoxide
-
The first highly effective iron-catalyzed carbonylative Suzuki reaction has been developed. Substrates with electron-donating or electron-withdrawing functionality, ortho-substitution, as well as active groups proceeded smoothly, affording desired products in high yields. This protocol is economical, environmentally benign and practical for the synthesis of biaryl ketones. This journal is the Partner Organisations 2014.
- Zhong, Yanzhen,Han, Wei
-
supporting information
p. 3874 - 3877
(2014/04/03)
-
- In situ generated nickel nanoparticle-catalyzed carbonylative Suzuki reactions of aryl iodides with arylboronic acids at ambient CO pressure in poly(ethylene glycol)
-
A general in situ generated nickel nanoparticle-catalyzed carbonylative Suzuki reactions of aryl iodides with arylboronic acids at atmospheric CO pressure in poly(ethylene glycol) has been demonstrated. A wide range of aryl iodides and arylboronic acids can be coupled to the corresponding biarylketones with high yields even in the absence of an added ligand and at low catalyst loading. The nature of the active catalytic species is discussed. This journal is
- Zhong, Yanzhen,Gong, Xinxing,Zhu, Xiaoshu,Ni, Zhuchao,Wang, Haoyang,Fu, Jinglin,Han, Wei
-
p. 63216 - 63220
(2015/02/19)
-
- A Palladium Bipyridyl Complex Grafted onto Nanosized MCM-41 as a Heterogeneous Catalyst for Negishi Coupling
-
The Negishi coupling of aryl bromides or acyl chlorides with organozinc chlorides catalyzed by a palladium bipyridyl complex anchored on nanosized mobile crystalline material 41 (MCM-41) were investigated. The reactions proceeded smoothly with a very low catalyst loading in THF at 70°C for electron-deficient aryl bromides, which gave good to high yields of the Negishi coupling products. However, reactions in toluene at 110°C were required if electron-rich aryl bromides were employed. For acyl chlorides, the reactions could be performed in THF at 50°C and the corresponding ketones and ynones were obtained in high yields. After centrifugation, it was possible to easily recover the supported catalyst from the reaction mixture, and this could be reused several times without any retreatment or regeneration with only a slight decrease in activity.
- Wu, Wei-Yi,Lin, Tze-Chiao,Takahashi, Tamotsu,Tsai, Fu-Yu,Mou, Chung-Yuan
-
p. 1011 - 1019
(2013/05/09)
-
- Catalytic Friedel-Crafts acylation: Magnetic nanopowder CuFe 2O4 as an efficient and magnetically separable catalyst
-
Catalytic regioselective Friedel-Crafts acylation of an array of anisoles/arenes with various acid chlorides using 5-20 mol % of magnetic nanopowder CuFe2O4 is reported. Unlike the conventional Friedel-Crafts reactions, which are catalyzed by moisture sensitive homogeneous catalysts/promoters, the nanopowder CuFe2O4 catalyst is moisture insensitive and the product/ketone-catalyst isolation is easily achieved using the magnetic properties of CuFe2O4.
- Parella, Ramarao,Naveen,Kumar, Amit,Babu, Srinivasarao Arulananda
-
p. 1738 - 1742
(2013/03/28)
-
- Towards applications of metal-organic frameworks in catalysis: Friedel-Crafts acylation reaction over IRMOF-8 as an efficient heterogeneous catalyst
-
A highly porous metal-organic framework (IRMOF-8) was synthesized by a solvothermal method, and used as an efficient heterogeneous catalyst for the Friedel-Crafts acylation reaction. The solid catalyst was characterized by X-ray powder diffraction (XRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM), thermogravimetric analysis (TGA), Fourier transform infrared spectroscopy (FT-IR), atomic absorption spectrophotometry (AAS), and nitrogen physisorption measurements. High conversions were achieved in the presence of a catalytic amount of the IRMOF-8 (1-5 mol%) without the need for an inert atmosphere. The solid catalyst could be facilely separated from the reaction mixture by simple centrifugation, and could be reused without a significant degradation in catalytic activity. No contribution from homogeneous catalysis of active acid species leaching into the reaction solution was detected.
- Nguyen, Lien T.L.,Nguyen, Chi V.,Dang, Giao H.,Le, Ky K.A.,Phan, Nam T.S.
-
body text
p. 28 - 35
(2011/11/30)
-
- MoO2Cl2 as a novel catalyst for Friedel-Crafts acylation and sulfonylation
-
The use of MoO2Cl2 as a novel catalyst for Friedel-Crafts acylation and sulfonylation is described. A series of aromatic ketones and sulfones were prepared in moderate to good yields using acyl chloride or sulfonyl chloride in the presence of MoO2Cl2 (20 mol %), under solvent-free conditions.
- de Noronha, Rita G.,Fernandes, Ana C.,Rom?o, Carlos C.
-
experimental part
p. 1407 - 1410
(2009/06/18)
-
- Palladium-phosphinous acid-catalyzed cross-coupling of aryl and acyl halides with aryl-, alkyl-, and vinylzinc reagents
-
(Chemical Equation Presented) Several palladium-phosphinous acids have been prepared and employed in cross-coupling reactions of aryl or acyl halides with aliphatic and aromatic organozinc reagents. The POPd7-catalyzed reaction of aryl halides, including electron-rich aryl chlorides, and arylzinc reagents was found to afford biaryls exhibiting alkoxy, alkylthio, amino, ketone, cyano, nitro, ester, and heteroaryl groups in 75-93% yield. Excellent results were obtained with sterically hindered substrates which gave di- and tri-ortho-substituted biaryls in up to 92% yield. Aryl halides also undergo POPd7-catalyzed aryl-vinyl and aryl-alkyl bond formation under mild conditions. Styrenes and alkylarenes were prepared in 79-93% yield from aryl halides and vinyl or alkylzinc reagents. The replacement of aryl halides by acyl halides provides access to ketones which were produced in up to 98% yield when POPd was used as catalyst. This approach overcomes the limited substrate scope, reduced regiocontrol, and low functional group tolerance of traditional Friedel-Crafts acylation methods.
- Xu, Hanhui,Ekoue-Kovi, Kekeli,Wolf, Christian
-
p. 7638 - 7650
(2008/12/22)
-
- Sterically hindered benzophenones via rhodium-catalyzed oxidative arylation of aldehydes
-
(Chemical Equation Presented) Efficient cross-coupling, allowing a straightforward access to congested benzophenones, between aromatic aldehydes and potassium aryltrifluoroborates, is described in the presence of a rhodium/tri-tert-butylphosphane catalyst system and acetone as cosolvent. The use of the stable phosphonium salts of tri-tert-butylphosphane prevented the use of highly oxidizable tri-tert-butylphosphane and allowed a careful control of the stoichiometry with the rhodium.
- Chuzel, Olivier,Roesch, Alexander,Genet, Jean-Pierre,Darses, Sylvain
-
p. 7800 - 7802
(2008/12/22)
-
- Tandem catalysis: Access to ketones from aldehydes and arylboronic acids via rhodium-catalyzed addition/oxidation
-
Direct cross-coupling reactions of aromatic aldehydes with arylboronic acids afforded ketones in high yields and under mild conditions in the presence of a rhodium catalyst, acetone and a base. This new reaction, involving a formal aldehyde C-H bond activation, is believed to proceed via a tandem process involving addition of the organometallic species to the aldehyde followed by oxidation by β-hydride transfer.
- Mora, Guilhem,Darses, Sylvain,Genet, Jean-Pierre
-
p. 1180 - 1184
(2008/09/16)
-
- Synthesis and structure-activity relationship for new series of 4-phenoxyquinoline derivatives as specific inhibitors of platelet-derived growth factor receptor tyrosine kinase
-
We discovered a new series of 4-phenoxyquinoline derivatives as potent and selective inhibitors of the platelet-derived growth factor receptor (PDGFr) tyrosine kinase. We researched the highly potent and selective inhibitors on the basis of both PDGFr and epidermal growth factor receptor (EGFr) inhibitory activity. First, we found a compound, Ki6783 (1), which inhibited PDGFr autophosphorylation at 0.13 μM, but it did not inhibit EGFr autophosphorylation at 100 μM. After extensive explorations, we found the two desired compounds, Ki6896 (2) and Ki6945 (3), which are substituted by benzoyl and benzamide at the 4-position of the phenoxy group on 4-phenoxyquinoline, respectively. These inhibitory activities were 0.31 and 0.050 μM, respectively, but neither of them inhibited EGFr autophosphorylation at 100 μM. We further investigated the profile of both compounds toward various tyrosine and serine/threonine kinases. The three compounds specifically inhibited PDGFr rather than the other kinases.
- Kubo, Kazuo,Ohyama, Shin-Ichi,Shimizu, Toshiyuki,Takami, Atsuya,Murooka, Hideko,Nishitoba, Tsuyoshi,Kato, Shinichiro,Yagi, Mikio,Kobayashi, Yoshiko,Iinuma, Noriko,Isoe, Toshiyuki,Nakamura, Kazuhide,Iijima, Hiroshi,Osawa, Tatsushi,Izawa, Toshio
-
p. 5117 - 5133
(2007/10/03)
-
- Photochromic compounds
-
A photochromic compound suitable for use as a single substance for photochromic tinting of a transparent plastic article so that the tinted article has a neutral gray or brown color in the excited state, is made by fusing at least two non-identical photochromic sections to an aromatic structure. The photochromic sections are selected so that the different absorption wavelengths of the excited photochromic sections give rise to a neutral gray or brown color in the plastic material and are selected from the group consisting of oxazines and pyrans. At least one of the photochromic sections is not an indolino spiropyran. The aromatic structure to which the photochromic sections are fused is selected from the group consisting of benzene, biphenyl, naphthalene, anthracene and phenanthrene. The positions of fusion of the photochromic sections on the aromatic structure are directly adjacent to the oxygen atom of the pyran or the oxygen or nitrogen atom of the oxazine.
- -
-
-
- Palladium-imidazolium-catalyzed carbonylative coupling of aryl diazonium ions and aryl boronic acids
-
Palladium(II) acetate and N,N-bis-(2,6-diisopropylphenyl)dihydroimidazolium chloride (2 mol%) were used to catalyze the carbonylative coupling of aryl diazonium tetrafluoroborate salts and aryl boronic acids to form aryl ketones. Optimal conditions includ
- Andrus, Merritt B.,Ma, Yudao,Zang, Yunfu,Song, Chun
-
p. 9137 - 9140
(2007/10/03)
-
- Quinoline and quinazoline derivatives inhibiting platelet-derived growth factor receptor autophosphorylation and pharmaceutical compositions containing the same
-
The present invention relates to novel quinoline derivatives and quinazoline derivatives represented by the following formula (I): STR1 [wherein R 1 and R 2 are each independently H or C 1 -C 4 -alkyl, or R 1 and R 2 together form C 1 -C 3 -alkylene, X is O, S or CH 2, W is CH or N, and Q is a substituted aryl group or substituted heteroaryl group] and their pharmaceutically acceptable salts, having platelet-derived growth factor receptor autophosphorylation inhibitory activity, to pharmaceutical compositions containing these compounds, and to methods for the treatment of diseases associated with abnormal cell growth such as tumors.
- -
-
-
- The catalytic Friedel-Crafts acylation reaction starting from aromatic compounds and free carboxylic acids (or their trimethylsilyl esters) by promotion of silicon (IV) cationic species via mixed anhydrides
-
In the presence of active cationic species generated from silicon(IV) chloride and silver perchlorate, carboxylic acids or their trimethylsilyl esters react with p-trifluoromethylbenzoic anhydride to form corresponding mixed anhydrides in situ. Then the catalytic Friedel-Crafts acylation reaction between initially formed mixed anhydrides and coexisted aromatic compounds smoothly proceeds at room temperature to afford the corresponding aromatic ketones in high yields. The above two sequential reactions are effectively promoted by the active silicon(IV) catalyst under mild conditions.
- Suzuki,Kitagawa,Mukaiyama
-
p. 3729 - 3734
(2007/10/02)
-
- Photochromic naphthopyran compounds
-
Described are novel reversible photochromic naphthopyran compounds having at least one ortho substituted phenyl group at the 3-position of the pyran ring. Also described are organic host materials that contain or that are coated with such compounds. Articles such as ophthalmic lenses or other plastic transparencies that incorporate the novel naphthopyran compounds or combinations thereof with complementary photochromic compounds, e.g., spiro(indolino)-oxazine type compounds, are also described.
- -
-
-
- REACTIONS OF β-SULFINYL α,β-UNSATURATED KETONES WITH DIENES
-
β-Sulfinyl α,β-unsaturated ketones (2a-f) reacted in a regioselective manner with dienes such as butadiene (3a) and 1,3-pentadiene (3b) to give 1,4-cyclohexadiene derivatives (4-8) with the concomitant elimination of sulfenic acid, while the ketones (2a-c) reacted with cyclopentadiene (3c) to yield the norbornenes (9).
- Nishio, Takehiko,Tokunaga, Tatsuhiro,Omote, Yoshimori
-
p. 2083 - 2094
(2007/10/02)
-
- SOME RELATIONSHIPS GOVERNING THE DEACYLATION OF SUBSTITUTED 9-BENZOYLANTHRACENES
-
In the presence of small amounts of ferric chloride substituted 9-benzoylanthracenes are deacylated, isomerized, and reacylated.The degree of transformation of the ketones increases with increase in the effective volume of the substituent at the ortho position to the acyl and with increase in the electron-donating characteristics of the substituent in the aromatic rings.
- Bokova, A. I.,Buchina, I. K.
-
p. 1199 - 1201
(2007/10/02)
-
- Acylierung von Aromaten mit Carbonsaeure-dihalogenphosphorsaeure-anhydriden
-
Aryl ketones 4, 9 are formed in good yields without the addition of Friedel-Crafts catalysts from activated arenes (e. g. alkylbenzenes, anisole) and aryl- and alkylcarboxylic dihalophosphoric anhydrides 1, 2, and 7, 8, respectively.The anhydrides 7, 8 may be prepared in situ by mixing the respective carboxylic and dihalophosphoric anhydrides.This procedure is especially advantageous in care of the less stable compounds.
- Effenberger, Franz,Koenig, Gerd,Klenk, Herbert
-
p. 926 - 936
(2007/10/02)
-