- Visible-Light-Driven Direct Oxidative Coupling Reaction Leading to Alkyl Aryl Ketones, Catalyzed by Nano Pd/ZnO
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Direct alkyl sp3 C–H activation to form new C–C bonds is one of the major challenges in synthetic chemistry. Herein, for the first time, we represent a new method, using nano Pd/ZnO which plays both as photoredox and transition-metal catalyst, for C–C bond formations. By using this catalyst, we have accomplished an oxidative coupling reaction between aryl halides and tertiary amines to yield the corresponding naturally occurring alkyl aryl ketones by using visible light irradiation. Furthermore, the carbonylation process was carried out on a 10 gram scale, with visible light and thermal condition, and it was proved to be scalable, efficient, and economical.
- Bazyar, Zahra,Hosseini-Sarvari, Mona
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supporting information
p. 2282 - 2288
(2019/04/03)
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- Chemoselective synthesis of ketones and ketimines by addition of organometallic reagents to secondary amides
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The development of efficient and selective transformations is crucial in synthetic chemistry as it opens new possibilities in the total synthesis of complex molecules. Applying such reactions to the synthesis of ketones is of great importance, as this motif serves as a synthetic handle for the elaboration of numerous organic functionalities. In this context, we report a general and chemoselective method based on an activation/addition sequence on secondary amides allowing the controlled isolation of structurally diverse ketones and ketimines. The generation of a highly electrophilic imidoyl triflate intermediate was found to be pivotal in the observed exceptional functional group tolerance, allowing the facile addition of readily available Grignard and diorganozinc reagents to amides, and avoiding commonly observed over-addition or reduction side reactions. The methodology has been applied to the formal synthesis of analogues of the antineoplastic agent Bexarotene and to the rapid and efficient synthesis of unsymmetrical diketones in a one-pot procedure. Macmillan Publishers Limited. All rights reserved.
- Bechara, William S.,Pelletier, Guillaume,Charette, Andre B.
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experimental part
p. 228 - 234
(2012/06/01)
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- Pentamethylcyclopentadienyl ruthenium: an efficient catalyst for the redox isomerization of functionalized allylic alcohols into carbonyl compounds
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The catalytic activity of the ruthenium(II) complex [RuCp*(CH3CN)3][PF6] 1 in the transposition of allylic alcohols into carbonyl compounds, in acetonitrile, is reported. This catalyst has proven to be able to catalyze the transformation of poorly reactive and/or functionalized substrates under smooth conditions.
- Bouziane, Asmae,Carboni, Bertrand,Bruneau, Christian,Carreaux, Fran?ois,Renaud, Jean-Luc
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experimental part
p. 11745 - 11750
(2009/04/11)
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- Development of a robust and practical process for the Darzens condensation and α,β-epoxide rearrangement: Scope and limitations of the methodology
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A practical and robust process for the Darzens condensation of substituted benzaldehydes and subsequent α,β-epoxy rearrangement is reported. The process developed is both amenable to large scale and parallel synthesis. While electron-poor benzaldehydes gave mixtures of aryl ketones and 2-substituted aryl ketones in mediocre to low yields, electron-rich benzaldehydes were found to react in high yields with complete regioselectivity to form 2-substituted aryl ketones. Georg Thieme Verlag Stuttgart.
- Zimbron, Jeremy Malcolm,Seeger-Weibel, Manuela,Hirt, Hans,Gallou, Fabrice
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p. 1221 - 1226
(2008/12/22)
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- Unexpected formation of aryl ketones by palladium-catalyzed coupling of aryl bromides with vinylic acetates
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A palladium-catalyzed coupling reaction of aryl bromides with vinylic acetates in the presence of tributyitin methoxide has been described. Unexpected formation of aryl ketones was obtained. Preliminary mechanistic studies indicated that the reaction proceeded by the addition of the aryl moiety in the coordination sphere of palladium to a ketene.
- Jean, Mickael,Renaulty, Jacques,Uriac, Philippe,Capet, Marc,Van De Weghe, Pierre
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p. 3623 - 3625
(2008/02/12)
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- Thienopyrimidine ureas as novel and potent multitargeted receptor tyrosine kinase inhibitors
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A series of novel thienopyrimidine-based receptor tyrosine kinase inhibitors has been discovered. Investigation of structure-activity relationships at the 5- and 6-positions of the thienopyrimidine nucleus led to a series of N,N′-diaryl ureas that potentl
- Dai, Yujia,Guo, Yan,Frey, Robin R.,Ji, Zhiqin,Curtin, Michael L.,Ahmed, Asma A.,Albert, Daniel H.,Arnold, Lee,Arries, Shannon S.,Barlozzari, Teresa,Bauch, Joy L.,Bouska, Jennifer J.,Bousquet, Peter F.,Cunha, George A.,Glaser, Keith B.,Guo, Jun,Li, Junling,Marcotte, Patrick A.,Marsh, Kennan C.,Moskey, Maria D.,Pease, Lori J.,Stewart, Kent D.,Stoll, Vincent S.,Tapang, Paul,Wishart, Neil,Davidsen, Steven K.,Michaelides, Michael R.
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p. 6066 - 6083
(2007/10/03)
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- Thiopyrimidine and isothiazolopyrimidine kinase inhibitors
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Compounds having the formula are useful for inhibiting protein tyrosine kinases. The present invention also discloses methods of making the compounds, compositions containing the compounds, and methods of treatment using the compounds.
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Page/Page column 14
(2008/06/13)
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- Kinase inhibitors
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The present application is directed to pyrazolopyrirnidine and furopyrimidine analogs of the formula (I) wherein the substituents are as defined herein, which are useful as kinase inhibitors.
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- Thiopyrimidine and isothiazolopyrimidine kinase inhibitors
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Compounds having the formula are useful for inhibiting protein tyrosine kinases. The present invention also discloses methods of making the compounds, compositions containing the compounds, and methods of treatment using the compounds.
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- Thiopyrimidine and isothiazolopyrimidine kinase inhibitors
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Compounds having the formula are useful for inhibiting protein tyrosine kinases. The present invention also discloses methods of making the compound, compositions containing the compounds, and methods of treatment using the compounds.
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- Kinase inhibitors
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The present application is directed to pyrazolopyrimidine and furopyrimnidine analogs of the formula (I) wherein the substituents are as defined herein, which are useful as kinase inhibitors.
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- Studies on pyrazines; 38: Acylation of bromopyrazines and 2-bromopyridine via copper-cocatalytic stille reaction
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Synthesis of acetylpyrazines 3 and propionylpyrazines 5 was achieved by copper-cocatalytic Stille reaction of bromopyrazines 1 with tributyl(1-ethoxyalkenyl)tin and then acidic hydrolysis. The optimal reaction conditions involve the combination of 15 molp
- Sato,Narita
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p. 1551 - 1555
(2007/10/03)
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- Ozone-mediated Nitration of Aromatic Ketones and Related Compounds with Nitrogen Dioxide
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Alkyl aryl ketones react smoothly with nitrogen dioxide at low temperatures in the presence of ozone to give ortho- and meta-nitro derivatives as the principal products, the former usually being predominant (ortho:meta = 1.1-3.8:1.0).No attack was observed on the alkyl side chains.
- Suzuki, Hitomi,Murashima, Takashi
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p. 903 - 908
(2007/10/02)
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- HENRY CONDENSATION UNDER HIGH PRESSURE. 2. EFFECT OF AROMATIC ALDEHYDE TYPE AND PRESSURE ON THE YIELD OF ω-NITROSTYRENES AND SECONDARY PROCESSES
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Condensation of aromatic aldehydes (I)-(XX) with EtNO2 and n-PrNO2 in AcOH in the presence of AcONH4 or i-BuNH2 gives primarily ω-nitrostyrenes (Ia, b) - (XXa, b) and small quantities of nitriles (Ic) - (XXc), oximes (Id) - (XXd), and ketones (Ie, f) - (XXe, f).The yields of (Ia, b) - (XXa, b) at P = 1 atm are higher for acceptor substitutents on the aromatic ring whereas at P = 10 kbar, they are higher for donor substituents.High pressures suppress the formation of (Ic-f) - (XXc-f) and the Z-isomers of (Ia, b) - (XXa, b).The high pressure technique is especially useful in the preparation of donor-substituted (Ia, b) - (XXa, b) which are intermediates in the synthesis of the psychotropic β-phenylethylamines.
- Agafonov, N. E.,Sedishev, I. P.,Dudin, A. V.,Kutin, A. A.,Stashina, G. A.,Zhulin, V. M.
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p. 366 - 372
(2007/10/02)
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- Preparation of Nitrobenzaldehydes and Nitrophenyl Ketones by Electrophilic Amination of Nitrobenzyl Aryl Sulfones
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Nitrobenzyl aryl sulfones 1a-g react with 3,3-pentamethylene-oxaziridine (2) with incorporation of an NH group into the benzylic position, followed by cleavage to nitrobenzaldehydes 4a-d and nitrophenyl ketones 4e-g, respectively.
- Wulf, Jens-Peter,Sienkiewicz, Krzysztof,Makosza, Mieczyslaw,Schmitz, Ernst
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p. 537 - 538
(2007/10/02)
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- Photochemical and Thermal Hydrations of Aromatic Allenes. Evidence for Allyl and Vinyl Cation Intermediates
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The photohydration of aromatic allenes has been studied in water and in dilute aqueous sulfuric acid (0-25percent H2SO4).It was found that phenylallene (2a) and α-methylphenylallene (2b) undergo photohydration to give the corresponding cinnamyl alcohol derivatives.The proposed mechanism involves protonation of the central carbon of phenylallenes in their singlet excited state (S1).In contrast, (p-nitrophenyl)allene (2g) and (m-nitrophenyl)allene (2h) gave the corresponding (nitrophenyl)acetones.The mechanism for the formation of these ketones is believed to be due to initial protonation of the α- or γ-carbon atom of the (nitrophenyl)allene in the triplet excited state (T1).Phenylallenes with CN, CF3, and F substituents failed to photohydrate.The results of these photohydrations were compared with those of the much slower thermal hydrations in 70-83percent H2SO4.Phenylallenes 2a and 2b cyclized to the corresponding indene derivatives in 70percent H2SO4.Phenylallenes with NO2-substituents (2g-2h) underwent hydration to give the corresponding (nitrophenyl)acetones (expected products) and (nitrophenyl)-1-propanones (unexpected products) in 83percent H2SO4.Similar results were obtained with (m-cyanophenyl)allene.The formation of both types of ketone is discussed in terms of the intermediacy of a common vinyl cation intermediate.
- Rafizadeh, Karim,Yates, Keith
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p. 1500 - 1506
(2007/10/02)
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