- Uncovering New Excited State Photochemical Reactivity by Altering the Course of the de Mayo Reaction
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An unprecedented and previously unknown photochemical reactivity of 1,3-dicarbonyl compounds is observed with amino-alkenes leading to dihydropyrans. This novel photochemical reactivity changes the established paradigm related to the De Mayo reaction between 1,3-dicarbonyl compounds and alkenes. This new reaction allows convenient access to the Marmycin core in a single step from commercially available reactants. The origin and scope of this new photoreaction is detailed with preliminary photophysical and mechanistic investigations.
- Kandappa, Sunil Kumar,Valloli, Lakshmy Kannadi,Jockusch, Steffen,Sivaguru, Jayaraman
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supporting information
p. 3677 - 3681
(2021/04/07)
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- I2-Promoted [3+2] Cyclization of 1,3-Diketones with Potassium Thiocyanate: a Route to Thiazol-2(3H)-One Derivatives
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An I2-promoted strategy has been developed for the synthesis of thiazol-2(3H)-one derivatives from 1,3-diketones with potassium thiocyanate. This [3+2] cyclization reaction involves C?S and C?N bond formation and exhibits good functional group tolerance. A series of thiazol-2(3H)-one derivatives are obtained in moderate to good yields. (Figure presented.).
- An, Zhenyu,Liu, Yafeng,Yan, Rulong,Zhao, Pengbo
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supporting information
p. 3240 - 3244
(2021/06/16)
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- Multi-stimuli-responsive fluorescence of axially chiral 4-ene-β-Diketones
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A unique series of simple, smart, and chiral binaphthalene-substituted 4-ene-β-diketones molecules has been designed and prepared. Their optical properties, charge contribution, and transition process highly depend on their chemical structures. These π-conjugated materials are highly emissive in both solution and solid (emission quantum yield up to 68%), owing to the inhibition of enol-keto tautomerization and the effect of steric hindrance from binaphthalene. Through ethylenic bond hydrolysis, they can be used for not only cation/anion sensing but also chiral amino acids recognition. Moreover, at low concentrations, they have little cytotoxicity to living cells and can stain cytoplasm. Therefore, they afford a new platform in the design of multi-stimuli-responsive, smart, and chiral materials.
- Wu, Dehua,Fang, Xinyi,Song, Jintong,Qu, Lang,Zhou, Xiangge,Xiang, Haifeng,Wang, Jun,Liu, Jin
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- Discovery of pyrazole N-aryl sulfonate: A novel and highly potent cyclooxygenase-2 (COX-2) selective inhibitors
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Based on a new pyrazole sulfonate synthetic method, a novel class of molecules with a basic structure of pyrazole N-aryl sulfonate have been designed and synthesized. The interest in conducting intensive research stems from quite evident anti-inflammatory effects exhibited by the compounds in preliminary animal experiments. A series of compounds were synthesized by different substitutions of the R1, R2, and R3 groups. Within the series, 4-iodophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate and phenyl 5-methyl-3-(4-(trifluoromethyl) phenyl)-1H-pyrazole-1-sulfonate exhibited excellent anti-inflammatory activity (% inhibition of auricular edemas = 27.0 and 35.9, respectively); the in vivo analgesic activity of phenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate and 2-chlorophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate was confirmed to be effective (inhibition ratio of writhing = 50.7% and 48.5% separately), and compounds phenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate, 4-iodophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate and 2-chlorophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate were identified as selective COX-2 inhibitors (SI = 455, 10,497 and >189 severally). In Acute Oral Toxicity assays conducted in vivo, the lethal dose 50 (LD50) of 4-iodophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate and 2-chlorophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate to mice was >2000 mg/kg BW.
- Guo, Quanping,Wang, Mengran,Wang, Rui,Xu, Zhaoqing,Yao, Haiyan
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- Pyrrolecarboxylic acid derivative synthesis method
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The invention discloses a pyrrolecarboxylic acid derivative synthesis method, which comprises: obtaining a group substituted formylacetone derivative by using a group substituted acetyl derivative andethyl acetate as raw materials; carrying out cyclization with diethyl aminomalonate hydrochloride to generate a pyrrolecarboxylic acid derivative ethyl ester; and carrying out a hydrolysis reaction to obtain the target product pyrrolecarboxylic acid derivative. According to the present invention, the method has characteristics of mild reaction conditions, simple purification, high yield and highproduct purity, and is suitable for process amplification and mass production.
- -
-
Paragraph 0108; 0110; 0115
(2019/11/04)
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- Switching of Sulfonylation Selectivity by Nature of Solvent and Temperature: The Reaction of β-Dicarbonyl Compounds with Sodium Sulfinates under the Action of Iron-Based Oxidants
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Selectivity of sulfonylation of β-keto esters with sodium sulfinates under the action of iron(III) salts as oxidants can be regulated by the type of solvent used and the reaction temperature. α-Sulfonyl β-keto esters are obtained when the process is conducted in THF/H2O solution at 40 °C. The change of the solvent to iPrOH/H2O and refluxing of a reaction mixture provides α-sulfonyl esters – the products of successive sulfonylation-deacylation. When β-diketones are applied as starting materials, only α-sulfonyl ketones are formed. The reaction pathway includes sulfonylation of dicabonyl compounds under the action of Fe(III) to form α-sulfonylated dicarbonyl compounds, which are then attacked by a solvent as the nucleophile, resulting in the products of successive sulfonylation-deacylation. Participation of the solvent in the reaction pathway determines the products structure.
- Mulina, Olga M.,Pirgach, Dmitry A.,Nikishin, Gennady I.,Terent'ev, Alexander O.
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supporting information
p. 4179 - 4188
(2019/05/08)
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- Binuclear Schiff-base zinc(II) complexes: Synthesis, crystal structures and reactivity toward ring opening polymerization of rac-lactide
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Upon crystallization from DMF/diethyl ether or CH2Cl2/pyridine of tetracoordinated Zn(II) complexes containing either 4-fluorophenyl or 4-anisyl substituted O,N,O-tridentate Schiff base ligands and pyridine as auxiliary ligand, three new doubly phenoxide-bridged dimeric Zn(II) complexes were isolated and their catalytic properties for the ring opening polymerization (ROP) of rac-lactide were explored. The single-crystal XRD analysis allowed to corroborate the molecular structures of the binuclear complexes, showing that the pentacoordinated Zn(II) metal ion adopts a slightly distorted square pyramidal geometry. The basal plane Is formed by the O,N,O-donor set of the tridentate Schiff base ligand and a phenoxo bridging oxygen, while a pyridine or a DMF molecule is located at the apex of the pyramid. The binuclear complexes were employed as catalysts in the ROP of rac-lactide for polylactide (PLA) synthesis. Polymerization conditions such as reaction time, catalyst concentration and use of benzyl alcohol as cocatalyst were studied, as well as their influence on the conversion rate, average molecular weight and polydispersity of the obtained PLA. The catalyst substituted with fluorine was more reactive, but with a lower control on the molecular weight compared to the methoxy-substituted catalyst. On the other hand, the presence of pyridine as an auxiliary ligand generates an improvement in the polydispersity of PLA.
- González, Darío M.,Cisterna, Jonathan,Brito, Iván,Roisnel, Thierry,Hamon, Jean-René,Manzur, Carolina
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- Direct Access to Functionalized Indoles via Single Electron Oxidation Induced Coupling of Diarylamines with 1,3-Dicarbonyl Compounds
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Under aerobic copper catalysis, an unprecedented direct synthesis of functionalized indoles via single electron oxidation induced coupling of diarylamines with 1,3-dicarbonyl compounds is presented. The protocol proceeds with good functional group and substrate compatibility, the use of readily available feedstocks and naturally abundant catalyst system, high step and atom efficiency, as well as selectivity, which offers a platform for accessing a new class of indoles with the potential for the discovery of functional molecules.
- Liang, Taoyuan,Zhao, He,Gong, Lingzhen,Jiang, Huanfeng,Zhang, Min
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supporting information
p. 6736 - 6740
(2019/09/09)
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- Pyrazole compound containing N-aryl sulfonate and synthesis and application thereof
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The invention discloses a pyrazole compound containing N-aryl sulfonate. A structural formula of the pyrazole compound is shown in the description. Proofed by pharmacological study, the pyrazole compound has the advantages that the activity of cyclooxygenase 2 is inhibited; the high-efficiency inhibition function on the generation of cyclooxygenase 2 due to inflammation mediums is realized, so that the pyrazole compound can be used as an active matter, and the prepared anti-inflammation medicine can be used for treating the inflammations, such as rheumatic arthritis and rheumatalgia, and the diseases and symptoms, such as fevers.
- -
-
Paragraph 0021
(2018/07/10)
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- Rhodium(ii)-catalysed generation of cycloprop-1-en-1-yl ketones and their rearrangement to 5-aryl-2-siloxyfurans
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Donor-acceptor cyclopropenes formed from enoldiazoketones undergo catalytic rearrangement to 5-aryl-2-siloxyfurans via a novel mechanism that involves a nucleophilic addition of the carbonyl oxygen to the rhodium-activated cyclopropene.
- Marichev, Kostiantyn O.,Wang, Yi,Carranco, Alejandra M.,Garcia, Estevan C.,Yu, Zhi-Xiang,Doyle, Michael P.
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p. 9513 - 9516
(2018/08/28)
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- Design, synthesis, and evaluation of multitarget-directed ligands against Alzheimer's disease based on the fusion of donepezil and curcumin
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By fusing donepezil and curcumin, a novel series of compounds were obtained as multitarget-directed ligands against Alzheimer's disease. Among them, compound 11b displayed potent acetylcholinesterase (AChE) inhibition (IC50?=?187?nM) and the highest BuChE/AChE selectivity (66.3). Compound 11b also inhibited 45.3% Aβ1–42 self-aggregation at 20?μM and displayed remarkable antioxidant effects. The metal-chelating property of compound 11b was elucidated by determining the 1:1 stoichiometry for the 11b–Cu(II) complex. The excellent blood–brain barrier permeability of 11b also indicated the potential for the compound to penetrate the central nervous system.
- Yan, Jun,Hu, Jinhui,Liu, Anqiu,He, Lin,Li, Xingshu,Wei, Hui
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p. 2946 - 2955
(2017/05/25)
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- O -Iodoxybenzoic Acid (IBX)-Iodine Mediated One-Pot Deacylative Sulfonylation of 1,3-Dicarbonyl Compounds: A Synthesis of β-Carbonyl Sulfones
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A combination of o-iodoxybenzoic acid (IBX) and a catalytic amount of iodine is found to promote a facile one-pot deacylative sulfonylation reaction of 1,3-dicarbonyl compounds with sodium sulfinates to yield β-carbonyl sulfones. The present method provides the target products bearing a wide variety of functional groups in one step and in good yields.
- Katrun, Praewpan,Songsichan, Teerawat,Soorukram, Darunee,Pohmakotr, Manat,Reutrakul, Vichai,Kuhakarn, Chutima
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supporting information
p. 1109 - 1121
(2017/02/24)
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- ARYL BETA DIKETONES AND THEIR USE A ODORANTS
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The present invention refers to aryl beta diketones of the formula (I) wherein Y, R1, R2 and R3 have the same meaning as given in the description. The invention further refers to fragrance compositions and fragranced articles comprising them.
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Page/Page column 13; 17
(2017/12/09)
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- Synthesis and biological evaluation of 3-alkyl-1,5-diaryl-1H-pyrazoles as rigid analogues of combretastatin A-4 with potent antiproliferative activity
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A series of novel 3-alkyl-1,5-diaryl-1H-pyrazoles were synthesized as combretastatin A-4 (CA-4) analogues and evaluated for antiproliferative activity against three human cancer cell lines (SGC-7901, A549 and HT-1080). Most of the target compounds displayed moderate to potent antiproliferative activity, and 7k was found to be the most potent compound. Structure-activity relationships indicated that compounds with a trimethoxyphenyl A-ring at the N-1 position of the pyrazole skeleton were more potent than those with the A-ring at the C-5 position. Tubulin polymerization and immunostaining experiments revealed that 7k potently inhibited tubulin polymerization and disrupted tubulin microtubule dynamics in a manner similar to CA-4. Computational modelling demonstrated that the binding of 7k to the colchicine binding site on microtubules may involve a similar mode as CA-4.
- Xu, Qile,Qi, Huan,Sun, Maolin,Zuo, Daiying,Jiang, Xuewei,Wen, Zhiyong,Wang, Zhiwei,Wu, Yingliang,Zhang, Weige
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- Aged red wine pigments as a source of inspiration for organic synthesis - The cases of the color-stable pyranoflavylium and flavylium-(4→8)-flavan chromophores
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Two flavylium-based chromophores peculiar to aged red wine pigments are investigated from a synthetic viewpoint. The condensation between easy-to-prepare 5-hydroxy-4-methylflavylium salts and aldehydes, giving birth to color-stable pyranoflavylium pigments, further proves efficient and wide in scope. A set of some twenty structurally-related flavylium-based pigments has been prepared and structure:color relationships are discussed. Furthermore, the synthesis of the flavylium-(4→8)-flavan chromophore is achieved via a novel three-step sequence. The elaborated sequence starts with an iodine-magnesium exchange from an 8-iodinated flavan, thus generating a magnesiated species that then smoothly reacts with a flavone to furnish an adduct, that finally leads to the expected chromophore via dehydration.
- Chassaing, Stefan,Isorez-Mahler, Géraldine,Kueny-Stotz, Marie,Brouillard, Raymond
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p. 3066 - 3078
(2015/05/04)
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- H2O2-promoted reactions of aliphatic primary amines with 1,3-diketones for the synthesis of 1 H -pyrrol-3(2 H)-ones at ambient temperature in water
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A green organic reaction of aliphatic primary amines with 1,3-diketones promoted by 30% aqueous H2O2 has been developed. It provides an inexpensive, regioselective, and efficient approach to 1H-pyrrol-3(2H)-ones with high yields from the simple and readily available starting materials in one pot via multicomponent tandem cyclization reactions and C-C cleavage under very mild and environmentally friendly reaction conditions.
- Sun, Xi,Li, Pinhua,Zhang, Xiuli,Wang, Lei
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supporting information
p. 2126 - 2129
(2014/05/06)
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- Discovery and structure-activity relationships study of novel thieno[2,3-b]pyridine analogues as hepatitis C virus inhibitors
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Current treatment for hepatitis C is barely satisfactory, there is an urgent need to develop novel agents for combating hepatitis C virus infection. This study discovered a new class of thieno[2,3-b]pyridine derivatives as HCV inhibitors. First, a hit compound characterized by a thienopyridine core was identified in a cell-based screening of our privileged small molecule library. And then, structure activity relationship study of the hit compound led to the discovery of several potent compounds without obvious cytotoxicity in vitro (12c, EC50 = 3.3 μM, SI >30.3, 12b, EC50 = 3.5 μM, SI >28.6, 10l, EC50 = 3.9 μM, SI >25.6, 12o, EC 50 = 4.5 μM, SI >22.2, respectively). Although the mechanism of them had not been clearly elucidated, our preliminary optimization of this class of compounds had provided us a start point to develop new anti-HCV agents.
- Wang, Ning-Yu,Zuo, Wei-Qiong,Xu, Ying,Gao, Chao,Zeng, Xiu-Xiu,Zhang, Li-Dan,You, Xin-Yu,Peng, Cui-Ting,Shen, Yang,Yang, Sheng-Yong,Wei, Yu-Quan,Yu, Luo-Ting
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supporting information
p. 1581 - 1588
(2014/03/21)
-
- Palladium-catalysed carbonylative α-arylation of acetone and acetophenones to 1,3-diketones
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Three COmponent α-arylation: A carbonylative ketone α-arylation process employing acetone for the first time, as well as acetophenones, is described (see scheme). The reaction tolerates a range of (hetero)aryl iodides and several functionalised aryl ketone coupling partners. Only low pressures of molecular CO are applied and no additional solvent is necessary. Copyright
- Schranck, Johannes,Tlili, Anis,Alsabeh, Pamela G.,Neumann, Helfried,Stradiotto, Mark,Beller, Matthias
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supporting information
p. 12624 - 12628
(2013/10/01)
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- Highly atom-efficient oxidation of electron-deficient internal olefins to ketones using a palladium catalyst
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A 100 % atom-efficient synthesis of ketones from electron-deficient internal olefins was achieved using O2 as a "green" oxidant (see scheme, DMA=N,N-dimethylacetamide, EWG=electron-withdrawing group). Various electron-deficient olefins were oxidized to the corresponding ketones with over 99 % selectivity and without the formation of olefin isomers or their oxidized products. Copyright
- Mitsudome, Takato,Yoshida, Syuhei,Mizugaki, Tomoo,Jitsukawa, Koichiro,Kaneda, Kiyotomi
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p. 5961 - 5964
(2013/06/27)
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- Synthesis of aryl-substituted or aryl-fused N-hydroxyethyl and N-hydroxymethypyrazole derivatives as potential ligands for the estrogen receptor
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A new series of N-hydroxyethylpyrazole (12a-f) and N-hydroxymethylpyrazole derivatives (15a-f) were designed for their estrogenic activities, having a 11.0 ± 0.5 A distance between their two hydroxyl groups, aliphatic-OH and phenolic-OH similar to 17β-estradiol (E2) as an endogenous hormone. To synthesize the title compounds, the key intermediate 1,3-dicarbonyl derivatives (2 and 8), were treated with hydrazine hydrate to produce the pyrazole ring 5 and 9. Further hydroxyalkylation of the latter produced the title pyrazoles. The position of hydroxyethyl or hydroxymethyl substituents in the products was determined through 2D NOE NMR spectroscopy.
- Allahyari-Devin, Maryam,Abedi, Behnam,Navidpour, Latifeh,Shafiee, Abbas
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- Enantioselective synthesis of optically pure β-amino ketones and γ-aryl amines by Rh-catalyzed asymmetric hydrogenation
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A series of optically pure β-amino ketones have been synthesized in high enantioselectivities (ee > 99%) by Rh-DuanPhos-catalyzed asymmetric hydrogenation of readily prepared β-keto enamides. Further reduction of these β-amino ketones with hydrogen and Pd/C leads to the formation of a variety of protected enantiomerically pure γ-aryl amines (ee > 99%), which are key building blocks in many bioactive molecules.
- Geng, Huiling,Huang, Kexuan,Sun, Tian,Li, Wei,Zhang, Xiaowei,Zhou, Le,Wu, Wenjun,Zhang, Xumu
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supporting information; experimental part
p. 332 - 334
(2011/03/19)
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- Te-1-acylmethyl and Te-1-iminoalkyl telluroesters: Synthesis and thermolysis leading to 1,3-diketones and O-alkenyl and O-imino esters
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A series of Te-1-acylmethyl carbotelluroates was prepared in good isolated yields from the reaction of potassium carbotelluroates with -haloketones in acetonitrile. Thermolysis of the telluroesters afforded vinyl esters in 20-50% yields, while treatment of the carbotellurorates with potassium t-butanolate led to 1,3-diketones in 30-75% yields with the liberation of black tellurium. The reaction of potassium carbotelluroates with -haloaceto oximes gave O-acyl oximes in 50-70% yields via Te-1-iminomethylcarbotelluroates. Copyright Taylor & Francis Group.
- Nakaiida, Shoho,Kato, Shinzi,Niyomura, Osamu,Ishida, Masaru,Ando, Fumio,Koketsu, Jugo
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experimental part
p. 930 - 946
(2010/08/04)
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- 1,4-Addition of Bis(iodozincio)methane to α,β-Unsaturated ketones: Chemical and theoretical/computational studies
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1,4-Addition of bis(iodozincio)methane to simple α,β-unsaturated ketones does not proceed well; the reaction is slightly endothermic according to DFT calculations. In the presence of chlorotrimethylsilane, the reaction proceeded efficiently to afford a silyl enol ether of β-zinciomethyl ketone. The CZn bond of the silyl enol ether could be used in a cross-coupling reaction to form another C-C bond in a one-pot reaction. In contrast, 1,4-addition of the dizinc reagent to enones carrying an acyloxy group proceeded very efficiently without any additive. In this case, the product was a 1,3-diketone, which was generated in a novel tandem reaction. A theoretical/computational study indicates that the whole reaction pathway is exothermic, and that two zinc atoms of bis(iodozincio)methane accelerate each step cooperatively as effective Lewis acids.
- Sada, Mutsumi,Furayama, Taniyuki,Komagawa, Shinsuke,Uchiyama, Masanobu,Matsubara, Seijiro
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experimental part
p. 10474 - 10481
(2010/10/21)
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- Highly efficient indium(III)-mediated cyclisation of 5-hydroxy-1,3- diketones to 2,3-dihydro-4H-pyran-4-ones; Mechanistic insights from in situ Fourier transform infrared spectroscopy
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5-Hydroxy-1,3-diketones have been synthesised in a facile one-pot reaction from the treatment of acid chlorides with non-substituted ketones and LiHMDS. Subsequent cyclisation to 2,3-dihydro-4H-pyran-4-ones occurs rapidly and in high yield (89-99%) when mediated by anhydrous indium(iii) chloride. A spectroscopic study of the reaction using in situ Fourier transform infrared (FTIR) spectroscopy has shown the reaction to be highly dependent on temperature, metal complex formation and InCl3 concentration. Since the reaction is deactivated by the precipitation of [InCl3·(H 2O)3], the concurrent use of a stronger drying agent, such as molecular sieves 4 A or anhydrous MgSO4, allows the reaction to be successfully carried out at relatively low loadings of InCl 3 (1-10%). In their absence, the optimum reaction conditions were found to be a diketone:InCl3 ratio of 3:1 in toluene, and a reaction temperature of 80 °C.
- Andrews, Philip C.,Gee, William J.,Junk, Peter C.,Krautscheid, Harald
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supporting information; experimental part
p. 698 - 705
(2010/05/11)
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- Pyridizinone derivatives
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The present invention provides compounds of formula (I*): their use as H3 inhibitors, processes for their preparation, and pharmaceutical compositions thereof.
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Page/Page column 113
(2008/06/13)
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- Pyranone, thiopyranone, and pyridone inhibitors of phosphatidylinositol 3-kinase related kinases. Structure-activity relationships for DNA-dependent protein kinase inhibition, and identification of the first potent and selective inhibitor of the ataxia telangiectasia mutated kinase
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Structure-activity relationships have been investigated for inhibition of DNA-dependent protein kinase (DNA-PK) and ATM kinase by a series of pyran-2-ones, pyran-4-ones, thiopyran-4-ones, and pyridin-4-ones. A wide range of IC50 values were observed for pyranones and thiopyranones substituted at the 6-position, with the 3- and 5-positions proving intolerant to substitution. Related pyran-2-ones, pyran-4-ones, and thiopyran-4-ones showed similar IC50 values against DNA-PK, whereas the pyridin-4-one system proved, in general, ineffective at inhibiting DNA-PK. Extended libraries exploring the 6-position of 2-morpholinopyran-4-ones and 2-morpholino- thiopyrano-4-ones identified the first highly potent and selective ATM inhibitor 2-morpholin-4-yl-6-thianthren-1-yl-pyran-4-one (151C; ATM; IC50 = 13 nM) and revealed constrained SARs for ATM inhibition compared with DNA-PK. One of the most potent DNA-PK inhibitors identified, 2-(4-methoxyphenyl)-6- (morpholin-4-yl)pyran-4-one (16; DNA-PK; IC50 = 220 nM) effectively sensitized HeLa cells to the topoisomerase II inhibitor etoposide in vitro.
- Hollick, Jonathan J.,Rigoreau, Laurent J. M.,Cano-Soumillac, Celine,Cockcroft, Xiaoling,Curtin, Nicola J.,Frigerio, Mark,Golding, Bernard T.,Guiard, Sophie,Hardcastle, Ian R.,Hickson, Ian,Hummersone, Marc G.,Menear, Keith A.,Martin, Niall M. B.,Matthews, Ian,Newell, David R.,Ord, Rachel,Richardson, Caroline J.,Smith, Graeme C. M.,Griffin, Roger J.
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p. 1958 - 1972
(2008/02/02)
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- NOVEL DUAL ACTION RECEPTORS ANTAGONISTS (DARA) AT THE AT1 AND ETA RECEPTORS
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The present invention relates to new compounds of the formula [Chemical formula should be inserted here. Please see paper copy] wherein R1, R2, R3, and R31 are as specified herein. The invention also relates to a method for preparation thereof, as well as combinations of the new compounds with previously known agents. The invention also relates to the use of the above-mentioned compounds and combinations for the preparation of a medicament for treating hypertension of different kinds, alleviating organ damage of different kinds, treating or preventing diabetic nephropathy, treating endothelin and angiotensin mediated disorders, and treating prostate cancer.
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Page/Page column 237; 242
(2010/11/28)
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- Propargyl bromide as an excellent α-bromoacetone equivalent: Convenient and new route to α-aroylacetones
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A variety of α-aroylacetones 4a-g have been prepared in excellent yields following a new protocol wherein α-aminonitriles 1a-g as the aryl acyl anion equivalents readily react with propargyl bromide as the α-bromoacetone equivalent. The alkylated product undergoes one-pot unmasking of the keto functionality along with Markovnikov's hydration of the terminal alkyne with CuSO4·5H2O in aqueous methanol at 60 °C to furnish the desired target in excellent isolated yields.
- Mahalingam, Sakkarapalayam M.,Aidhen, Indrapal Singh
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p. 349 - 351
(2007/10/03)
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- Proline-catalyzed aldol reactions of acyl cyanides with acetone: An efficient and convenient synthesis of 1,3-diketones
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The aldol-type addition of acetone towards (un)substituted benzoyl, heteroarylcarbonyl or α,β-unsaturated acyl cyanides was efficiently catalyzed by l-proline (30 mol %) to give 2-hydroxy-4-oxo-2-substituted pentanenitriles. Upon the treatment with sodium hydroxide, the adducts transformed to 1,3-diketones in good-to-excellent yield, furnishing an efficient and convenient method for the regioselective synthesis of 1,3-diketones.
- Shen, Zongxuan,Li, Bin,Wang, Lu,Zhang, Yawen
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p. 8785 - 8788
(2007/10/03)
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- Pyrazoloisoquinoline derivative as kinase inhibitors for the treatment of various disorders
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Compounds of the formula I are suitable for producing pharmaceuticals for the prophylaxis and therapy of diseases whose course involves an increased activity of NIK.
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- PYRAZOLOISOQUINOLINE DERIVATIVES AS KINASE INHIBITORS
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Novel pyrazoloisoquinoline derivatives as kinase inhibitors are disclosed which are suitable for producing pharmaceuticals for the prophylaxis and therapy of diseases whose course involves an increased activity of NIK.
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Page/Page column 36
(2010/02/10)
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- Palladium-Catalyzed Oxidative Alkoxylation of α-Alkenyl β-Diketones to Form Functionalized Furans
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Treatment of 4-allyl-2,6-dimethyl-3,5-heptanedione with a catalytic amount of PdCl2(CH3CN)2 (5 mol %) and a stoichiometric amount of CuCl2 (2.2 equiv) in dioxane at 60 °C for 12 h formed 3-isobutyryl-2-isopropyl-5-methylfuran in 77% isolated yield. A number of α-alkenyl β-dike-tones underwent oxidative alkoxylation under these conditions to form 2,3,5-trisubsituted furans in moderate to good yield.
- Han, Xiaoqing,Widenhoefer, Ross A.
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p. 1738 - 1740
(2007/10/03)
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- PYRAZOLOISOQUINOLINE DERIVATIVES FOR INHIBITING NFKAPPAB-INDUCING KINASE (NIK)
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The invention relates to compounds of formula (I), which are suitable for producing medicaments for the prophylaxis and treatment of diseases, the progression of which involves an increased activity of NIK.
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Page/Page column 23
(2008/06/13)
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- Substituted oxazoles and thiazoles derivatives as hPPARγ and hPPARα activators
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The present invention discloses compounds of formula (I), and tautomeric forms, pharmaceutically acceptable salts, or solvates thereof. Preferably, the compounds of the invention are dual activators of hPPARγ and hPPAR{acute over (α)}.
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- Copper(II/I) complexes of a bulky tris(pyrazolylmethyl)amine ligand
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The ligand tris[3-(4-methoxyphenyl)-5-methylpyrazol-1-ylmethyl]amine (L), the copper(II) complexes [CuLCL2] 1, [CuLCL][SbF6] 2 and [CuL(H2O)][SbF6]2 3, and the copper(I) complex [CuL][CF3SO3] 4 have been prepared. Complexes 1-3 are reduced by [BPh4]- ion in a range of solvents to afford [CuL]+ ion. The [CuL]+ ion does not react with dioxygen nor carbon monoxide but does reat with chloride ion. Physicochemical and cyclic voltammetry data are reported for 1/4, along with crystal structure analyses of 1-3 and [CuL][CuCl2]. There are some notable differences between the structures and properties of these copper complexes and those reported for analogues with pyridyl- or imidazolyl amine ligands.
- Chen, Zhixuan (Jack),Karasek, Natasha,Craig, Donald C.,Colbran, Stephen B.
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p. 3445 - 3452
(2007/10/03)
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- A facile route to convert acetylacetone into other β-diketones with acyl chlorides promoted by samarium triiodide
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Reaction of acetylacetone with acyl chlorides in the presence of SmI3 gave β-diketones RCOCH2COCH3 (I) or RCOCH2COR (II) in good yields under mild and neutral conditions.
- Hao, Wenying,Zhang, Yongmin,Ying, Taokai,Lu, Pin
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p. 2421 - 2427
(2007/10/03)
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- 13C NMR Spectroscopic Study of the Tautomeric Equilibrium in p-Phenyl Substituted Benzoylacetones
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Solution 13C NMR chemical shifts are reported for a series of p-phenyl substituted benzoylacetones which undergo a fast, intramolecular proton-transfer reaction between both possible enol tautomers.This information, together with 13C NMR spectroscopic data for related non-exchanging model compounds, allows the study of substituent-induced equilibrium shifts.The results show a systematic trend: electron-withdrawing para groups shift the equilibrium towards the methyl keto form.
- Cravero, Raquel M.,Gonzalez-Sierra, Manuel,Olivieri, Alejandro C.
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p. 1067 - 1071
(2007/10/02)
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- Clemmensen Reduction. X. The Synthesis and Acidolysis of Some Aryl Alkyl Substituted Cyclopropane-1,2-diols
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The synthesis of a number of 1-alkyl-2-arylcyclopropane-1,2-diols is reported.Reductive treatment of suitably substituted 1,3-diketones gave a cyclopropanediyl diacetate from which the diol was obtained.Reaction of these diols with acid gave α-hydroxy ketones, in which an alkyl group, rather than an aryl group, was adjacent to the carbonyl function.Clemmensen reduction of the 1,3-diketones gave products of rearrangement, generally similar to those obtained by acidolysis of the cyclopropane-1,2-diols.The relationship of these results to thermochemical studies on the stability of carboxonium ions is discussed.
- Davis, Brian R.,Hinds, Mark G.,Ting, Philip P. C.
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p. 865 - 875
(2007/10/02)
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- An improved synthesis of 2-diazo-1,3-diketones
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The sodium hydride/dibenzo-18-crown-6 ether system was found to be an effective base for the synthesis of 1,3-diketones by the Claisen condensation. The use of potassium fluoride (with or without crown ether) as the base in diazo-transfer reactions extends this reaction to the synthesis of hindered diazo diketones. In the case of isomeric 1,3-diketones, the stereoselectivity of the process considerably rises.
- Popic,Korneev,Nikolaev,Korobitsyna
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p. 195 - 198
(2007/10/02)
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- Synthesis and characterization of cobalt(II) and some nickel(II) complexes with N,N′-ethylenebis(p-X-benzoylacetone iminato) and N,N′-ethylenebis(p-X-benzoylmonothioacetone iminato) ligands
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A series of tetradentate thio imine ligands, N,N′-ethylenebis(p-X-benzoylmonothioacetone imine), where X = H, CH3, CH3O, Br, and Cl, have been prepared from the corresponding tetradentate keto amines via nucleophilic substitution with bisulfide ion. Cobalt(II) complexes with all ligands have been prepared and characterized and are of particular interest because of their ability to combine reversibly with molecular oxygen in nonaqueous solutions at low temperatures. The new ligands and complexes have been characterized by elemental analyses and IR, NMR, and visible spectral data. A few of the corresponding Ni(II) complexes have also been prepared to aid in characterization via NMR techniques when the free ligands proved too insoluble for study.
- Chen, Loomis S.,Cummings, Sue C.
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p. 2358 - 2361
(2007/10/14)
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