- Ultra-fast Cycling for Multiplexed Cellular Fluorescence Imaging
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Rapid analysis of single and scant cell populations is essential in modern diagnostics, yet existing methods are often limited and slow. Herein, we describe an ultra-fast, highly efficient cycling method for the analysis of single cells based on unique li
- Ahmed, Maaz S.,Carlson, Jonathan C. T.,Ko, Jina,Oh, Juhyun,Weissleder, Ralph
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- Chemoselective Hydrogenation of Olefins Using a Nanostructured Nickel Catalyst
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The selective hydrogenation of functionalized olefins is of great importance in the chemical and pharmaceutical industry. Here, we report on a nanostructured nickel catalyst that enables the selective hydrogenation of purely aliphatic and functionalized olefins under mild conditions. The earth-abundant metal catalyst allows the selective hydrogenation of sterically protected olefins and further tolerates functional groups such as carbonyls, esters, ethers and nitriles. The characterization of our catalyst revealed the formation of surface oxidized metallic nickel nanoparticles stabilized by a N-doped carbon layer on the active carbon support.
- Klarner, Mara,Bieger, Sandra,Drechsler, Markus,Kempe, Rhett
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supporting information
p. 2157 - 2161
(2021/05/21)
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- Photoredox-Catalyzed Simultaneous Olefin Hydrogenation and Alcohol Oxidation over Crystalline Porous Polymeric Carbon Nitride
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Booming of photocatalytic water splitting technology (PWST) opens a new avenue for the sustainable synthesis of high-value-added hydrogenated and oxidized fine chemicals, in which the design of efficient semiconductors for the in-situ and synergistic utilization of photogenerated redox centers are key roles. Herein, a porous polymeric carbon nitride (PPCN) with a crystalline backbone was constructed for visible light-induced photocatalytic hydrogen generation by photoexcited electrons, followed by in-situ utilization for olefin hydrogenation. Simultaneously, various alcohols were selectively transformed to valuable aldehydes or ketones by photoexcited holes. The porosity of PPCN provided it with a large surface area and a short transfer path for photogenerated carriers from the bulk to the surface, and the crystalline structure facilitated photogenerated charge transfer and separation, thus enhancing the overall photocatalytic performance. High reactivity and selectivity, good functionality tolerance, and broad reaction scope were achieved by this concerted photocatalysis system. The results contribute to the development of highly efficient semiconductor photocatalysts and synergistic redox reaction systems based on PWST for high-value-added fine chemical production.
- Qiu, Chuntian,Sun, Yangyang,Xu, Yangsen,Zhang, Bing,Zhang, Xu,Yu, Lei,Su, Chenliang
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p. 3344 - 3350
(2021/07/26)
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- Bidentate NHC-Cobalt Catalysts for the Hydrogenation of Hindered Alkenes
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Herein, we report a series of easily accessible bidentate N-heterocyclic carbene (NHC) cobalt catalysts, which enable the hydrogenation of hindered alkenes under mild conditions. The four-coordinated bidentate NHC-Co(II) complexes were characterized by X-ray diffraction, elemental analysis, ESI-HRMS, and magnetic moment measurements, revealing a distorted-tetrahedral geometry and a high-spin configuration of the metal center. The activity of the in situ formed catalytic system, which was obtained from easily available NHC precursors, CoCl2, and NaHBEt3, was identical with those of well-defined NHC-cobalt catalysts. This highlights the potential utility of this reaction system.
- Wei, Zeyuan,Wang, Yujie,Li, Yibiao,Ferraccioli, Raffaella,Liu, Qiang
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p. 3082 - 3087
(2020/10/02)
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- N-Alkylation of N-trimethylsilyl derivatives of lactams, amides, and imides with alkyl sulfonates
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The reaction of N-trimethylsilyl derivatives of amides and imides with alkyl sulfonates on heating affords the corresponding N-alkyl derivatives and trimethylsilyl sulfonates.
- Baukov, Yu. I.,Kramarova, E. P.,Negrebetsky, Vad. V.,Shagina, A. D.,Shipov, A. G.,Tarasenko, D. V.
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p. 398 - 400
(2020/04/15)
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- Extending the chemical product tree: A novel value chain for the production of: N -vinyl-2-pyrrolidones from biogenic acids
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The sustainable production of polymers from biogenic platform chemicals shows great promise to reduce the chemical industry's dependence on fossil resources. In this context, we propose a new two-step process leading from dicarboxylic acids, such as succinic and itaconic acid, to N-vinyl-2-pyrrolidone monomers. Firstly, the biogenic acid is reacted with ethanolamine and hydrogen using small amounts of water as solvent together with solid catalysts. For effective conversion, the optimal catalyst (carbon supported ruthenium) has to hold the ability of activating H2 as well as (imide) CO bonds. The obtained products, N-(2-hydroxyethyl)-2-pyrrolidones, are subsequently converted in a continuous gas phase dehydration over simple sodium-doped silica, with excellent selectivity of above 96 mol% and water as the sole by-product. With a final product yield of ≥72 mol% over two process steps and very little waste due to the use of heterogeneous catalysis, the proposed route appears promising-commercially as well as in terms of Green Chemistry.
- Haus, Moritz Otto,Louven, Yannik,Palkovits, Regina
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p. 6268 - 6276
(2019/12/03)
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- Facile Preparation of N -Alkyl-2-pyrrolidones in a Continuous-Flow Microreactor
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N-Alkyl-2-pyrrolidones have been widely used in the petrochemical industry, the agricultural chemical industry, electronic materials, etc. The distinct advantages of using N-alkyl-2-pyrrolidones as solvents or reaction media make them particularly important. A continuous-flow microreactor was exploited for the preparation of N-methyl-2-pyrrolidone (NMP) and N-ethyl-2-pyrrolidone (NEP) in a highly controlled and safe manner; thus, its use improved the efficiency of the process. Various conditions (temperature, residence time, molar ratio of amine to γ-butyrolactone (GBL), GBL concentration, water content, and presence of H3BO3 catalyst) were investigated to improve the synthesis of NMP/NEP. A microreactor was employed for the conversion of GBL to NMP and NEP, and the yields reached 94.7% for NMP and 93.9% for NEP under the optimized conditions. Furthermore, a kinetic model based on the reaction mechanism was proposed to guide the design and optimization of the synthesis of NMP/NEP.
- Zhou, Feng,Zhang, Boyu,Liu, Hongchen,Wen, Zhenghui,Wang, Kejun,Chen, Guangwen
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p. 504 - 511
(2018/04/27)
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- Palladium/Phosphorus-Doped Porous Organic Polymer as Recyclable Chemoselective and Efficient Hydrogenation Catalyst under Ambient Conditions
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A new type of phosphorus-doped porous organic polymer (POP) has been readily synthesized through a Heck reaction, which could be used not only as a support but also a ligand for palladium nanoparticles. The dual-functional material supported palladium nanocatalyst was used for the efficient and chemoselective hydrogenation of varieties of nitroarenes and α,β-unsaturated compounds, as well as for the synthesis of indoles from 2-nitrophenylacetonitrile under 1 atm hydrogen in green solvents at room temperature. No obvious aggregation and loss of catalytic activity of the new nanocatalyst were observed after 10 runs in the reaction. (Figure presented.).
- Ding, Zong-Cang,Li, Cun-Yao,Chen, Jun-Jia,Zeng, Jia-Hao,Tang, Hai-Tao,Ding, Yun-Jie,Zhan, Zhuang-Ping
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p. 2280 - 2287
(2017/07/07)
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- Matrix-IR spectroscopic investigations of the thermolysis and photolysis of diazoamides
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Matrix photolysis of N,N-dialkyldiazoacetamides 1a-d at 7-10 K results in either the formation of C-H insertion products (in case of N,N-dimethyl and N,N-diethyl diazoamides) or almost exclusive Wolff rearrangement to ketenes (in the case of the cyclic di
- Wentrup, Curt,Bibas, Herve,Kuhn, Arvid,Mitschke, Ullrich,McMills, Mark C.
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p. 10705 - 10717
(2013/11/19)
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- N-alkyl functionalised expanded ring N-heterocyclic carbene complexes of rhodium(i) and iridium(i): Structural investigations and preliminary catalytic evaluation
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A series of new N-alkyl functionalised 6- and 7-membered expanded ring N-heterocyclic carbene (NHC) pro-ligands 3-6 and their corresponding complexes of rhodium(i) and iridium(i), [M(NHC)(COD)Cl] 7-14 and [M(NHC)(CO) 2Cl] 15-22 are described. The complexes have been characterised by 1H and 13C{1H} NMR, mass spectrometry, IR and X-ray diffraction. It is noted from X-ray diffraction studies that the N-alkyl substituents are found to orientate themselves away from the metal centre due to unfavourable steric interactions resulting in low percent buried volume (%Vbur) values in the solid state. The heterocycle ring size is also found to dictate the spatial orientation of the N-alkyl substituents in the neopentyl functionalised derivatives 10 and 14. The 7-membered derivative 14 allows for a conformational 'twist' of the heterocycle ring with the N-alkyl substituents adopting a mutually trans configuration with respect to each other, while the more rigid 6-membered system 10 does not allow for this conformational 'twist' and consequently the N-alkyl substituents adopt a mutually cis configuration. The σ-donor function of this new class of expanded ring NHC ligand has also been probed by measured IR stretching frequencies of the [M(NHC)(CO)2Cl] complexes 15-22. A preliminary catalytic survey of the hydrogenation of functionalised alkenes with molecular hydrogen under mild conditions has also been undertaken with complex 10, affording an insight into the application of large ring NHC ancillary ligands bearing N-alkyl substituents in hydrogenation transformations.
- Dunsford, Jay J.,Tromp, Dorette S.,Cavell, Kingsley J.,Elsevier, Cornelis J.,Kariuki, Benson M.
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p. 7318 - 7329
(2013/08/26)
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- Selective hydrogenation of alkenes under ultramild conditions
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SiliaCat Pd0 solid catalyst heterogeneously mediates at room temperature the selective hydrogenation of a wide variety of alkenes under hydrogen balloon conditions using a modest 0.1 mol % catalyst amount. The catalyst is recyclable with negligible leaching of valued palladium, providing the chemical industry with a suitable replacement for less selective metal-based catalysts.
- Pandarus, Valerica,Gingras, Genevieve,Beland, Francois,Ciriminna, Rosaria,Pagliaro, Mario
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experimental part
p. 1230 - 1234
(2012/07/28)
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- Hydroamination of unactivated alkenes catalyzed by novel platinum(II) N -heterocyclic carbene complexes
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Cationic platinum(II) complexes with bi- or tridentate (pincer) functionalized NHC ligands were found to be catalytically active in the hydroamination of unactivated alkenes. In some cases, the presence of water had an activating effect on the complexes. Reactions with the N-nucleophilic substrate morpholine led to a noncatalytic reaction in which the deprotonation product of the key cationic β-aminoalkyl platinum complex could be isolated and characterized. Surprisingly, attempted protonation of this complex did not give the expected N-alkylated product, indicating either the thermodynamic unfavorability of C-Pt bond cleavage or its kinetic inertness.
- Cao, Peng,Cabrera, Jose,Padilla, Robin,Serra, Daniel,Rominger, Frank,Limbach, Michael
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experimental part
p. 921 - 929
(2012/04/10)
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- Organocatalytic diimide reduction of enamides in water
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Bridged flavinium organocatalysts have displayed efficacy in the diimide mediated reduction of enamides in aqueous conditions. This represents the first diimide reduction of an electron rich alkene and offers a clean alternative to the use of alkylating agents for N-alkylation.
- Marsh, Barrie J.,Heath, Emma L.,Carbery, David R.
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supporting information; experimental part
p. 280 - 282
(2011/02/23)
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- A novel synthesis of ibutilide fumarate
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A novel protocol for the synthesis of Ibutilide Fumarate (raceme) was achieved from 2-pyrrolidinone with an overall yield of 15%. The core structure was constructed in one step based on Friedel-Crafts acylation with an acyl chloride containing an amino hydrochloride.
- Wang, Tao,Tian, Rui,Xiao, Bin,Shen, Yi,Zhou, Hui,Li, Qingeng
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experimental part
p. 423 - 426
(2012/05/07)
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- Synthesis of biobased N-methylpyrrolidone by one-pot cyclization and methylation of γ-aminobutyric acid
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N-Methylpyrrolidone (NMP) is an industrial solvent that is currently based on fossil resources. In order to prepare it in a biobased way, the possibility to synthesize NMP from γ-aminobutyric acid (GABA) was investigated, since GABA can be obtained from glutamic acid, an amino acid that is present in many plant proteins. Cyclization of GABA to 2-pyrrolidone and subsequent methylation of 2-pyrrolidone to NMP was achieved in a one-pot procedure, using methanol as the methylating agent and a halogen salt (i.e. ammonium bromide) as a catalyst. A selectivity above 90% was achieved, as well as a high conversion. Methylation of 2-pyrrolidone could also be done with dimethyl carbonate, but then the selectivity for NMP was less (67%).
- Lammens, Tijs M.,Franssen, Maurice C. R.,Scott, Elinor L.,Sanders, Johan P. M.
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scheme or table
p. 1430 - 1436
(2010/09/05)
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- Rediscovering copper-based catalysts for intramolecular carbon-hydrogen bond functionalization by carbene insertion
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A series of TpxCu complexes (Tpx = hydrotrispyrazolylborate ligand) have been tested as catalysts for the decomposition of several diazoacetates and N,N-disubstituted diazoacetamides and the subsequent formation of lactones and lacta
- Martin, Carmen,Belderrain, Tomas R.,Perez, Pedro J.
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supporting information; scheme or table
p. 4777 - 4781
(2009/12/08)
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- PROCESS FOR CONTINUOUSLY PREPARING N-ETHYL-2-PYRROLIDONE (NEP)
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Process for the continuous preparation of N-ethyl-2-pyrrolidone (NEP) by reacting gamma-butyrolactone (GBL) with monoethylamine (MEA) in the liquid phase, wherein GBL and MEA are used in a molar ratio in the range from 1:1.08 to 1:2 an the reaction is carried out at a temperature in the range from 320 to 420° C. and an absolute pressure in the range from 70 to 120 bar.
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Page/Page column 3
(2009/07/25)
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- Ultrafast time-resolved infrared spectroscopy study of the photochemistry of N,N-diethyldiazoacetamide: rearrangement in the excited state
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(Graph Presented) Ultrafast infrared spectroscopy shows that in chloroform, β-lactam is formed immediately after the laser pulse but γ-lactam is formed from both slow and fast processes. It is concluded that β-lactam is formed from the diazoamide excited state via the rearrangement in the excited state (RIES) mechanism and that γ-lactam is formed from both RIES and carbene. In methanol, both carbene decay and the rise of amide ether product are observed directly. Predictions from density functional theory calculations are consistent with these observations.
- Zhang, Yunlong,Burdzinski, Gotard,Kubicki, Jacek,Platz, Matthew S.
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supporting information; body text
p. 9646 - 9647
(2011/03/20)
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- The transition metal catalyzed hydroboration of enamines
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The addition of catecholborane (HBcat, cat = 1,2-O2C6H4) to 9-vinylcarbazole can give either the branched or linear hydroboration product depending upon the judicious choice of metal catalyst used in these reactions. Analo
- Geier, Michael J.,Vogels, Christopher M.,Decken, Andreas,Westcott, Stephen A.
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experimental part
p. 3154 - 3159
(2010/01/06)
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- Diruthenium(I,I) catalysts for the formation of β- and γ-lactams via carbenoid C-H insertion of α-diazoacetamides
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Intramolecular carbenoid C-H insertion of five α-diazoacetamides [N2CH-CONR2, NR2 = NEt2 (3a), NBu2 (3b), N(i-Pr)2 (3c), N(CH2Ph)2 (3d), N(i-Pr)(CH2Ph) (3e)], was investigated using as catalysts dinuclear Ru(I,I) complexes of the type [Ru2-(μ-L 1)2(CO)4L22], where L1 is a bidentate bridging acetate, calix[4]arenedicarboxylate, saccharinate, pyridin-2-olate, or triazenide ligand, as well as [RuCl 2(p-cymene)]2. The Ru(I,I) complexes were found to be suitable catalysts for the carbenoid cyclization reactions, except in the case of 3a. With diazoamides 3b-e, [Ru2(μ-sac)2(CO) 5]2 (sac=saccharinate) and [Ru2(μ-6- chloropyridin-2-olate)2(CH3CN)2(CO) 4] are as effective as Rh2(OAc)4 under the same conditions, although some differences in the regioselectivity and chemoselectivity of the cyclization are observed. The carbenoid cyclization reactions yield γ-lactams from diazoamides 3a and 3b, both a β- and a γ-lactam from 3c, and a β-lactam as well as a 3-azabicyclo-[5.3.0] deca-5,7,9-trien-2-one from 3d. With 3e, formation of γ-lactam 21 and of bicyclic lactam 23 prevails.
- Grohmann, Markus,Buck, Stefan,Schaeffler, Lutz,Maas, Gerhard
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p. 2203 - 2211
(2007/10/03)
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- Process for making N-vinyl-2-pyrrolidone
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A process for making N-vinyl-2-pyrrolidone (NVP) is disclosed. The process comprises dehydrating N-(2-hydroxyethyl)-2-pyrrolidone (HEP) in the presence of a catalyst and added water. Adding an effective amount of water into the dehydration process reduces the amount of N-ethyl-2-pyrrolidone (NEP) formed compared with the amount produced in the absence of the added water. Adding water can also sustain high conversions of HEP, minimize heavies formation, and improve selectivity to NVP. The process provides high-purity NVP and avoids a costly crystallization step.
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Page/Page column 4-6
(2008/06/13)
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- Synthesis, conformational characteristics and anti-influenza virus A activity of some 2-adamantylsubstituted azacycles
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The broad-spectrum antiviral activity of 2-(2-adamantyl)piperidines 11, 13a,b, and 15, 3-(2-adamantyl)pyrrolidines 27, 21a-g and 2-(2-adamantylmethyl)piperidines 30, 32a-c, and 35a-d was examined. Several compounds in the new series were potent against influenza A H3N2 virus. When 1-aminoethyl pharmacophore group of 2-rimantadine 4 (2-isomer of rimantadine) is included into a saturated nitrogen heterocycle, see compound 11, potency was retained. The diamine derivatives 21e-g and particularly 35a-c possessing three pharmocophoric groups, that is, the adamantyl and the two amine groups, exhibited high potency. The new compounds did not afford specific activity at non-toxic concentrations against any of the other viruses tested. According to NMR spectroscopy and molecular mechanics calculations it is striking that the parent structures 11 and 27 adopt a fixed trans conformation around C2{single bond}C2′ bond. In the parent amines, which proved to be active compounds, the distance between nitrogen and adamantyl pharmacophoric groups was different; N{single bond}C2′ distance is 3.7, 3.8 A for 27, 30 and 2.5 A for 11 suggesting that M2 receptor site can accommodate different in size and orientation lipophilic cages.
- Setaki, Despina,Tataridis, Dimitris,Stamatiou, George,Kolocouris, Antonios,Foscolos, George B.,Fytas, George,Kolocouris, Nicolas,Padalko, Elizaveta,Neyts, Johan,Clercq, Erik De
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p. 248 - 273
(2008/02/07)
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- Ammonium formate/palladium on carbon: A versatile system for catalytic hydrogen transfer reductions of carbon-carbon double bonds
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Various carbon-carbon double bonds in olefins and α,β -unsaturated ketones were effectively reduced to the corresponding alkanes and saturated ketones, using ammonium formate as a hydrogen transfer agent in the presence of Pd/C as catalyst in refluxing methanol.
- Paryzek, Zdzislaw,Koenig, Hanna,Tabaczka, Bartlomiej
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p. 2023 - 2026
(2007/10/03)
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- Process for the preparation of lactams
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The present invention is related to a method for preparing lactam represented by the following formula: wherein R is C2-10 alkylene which may be optionally substituted with C1-6 alkyl or phenyl; R is a hydrogen atom, C1-6 alkyl, C1-6 hydroxyalkyl or phenyl. The method for preparing lactam comprises an amination reaction using crystalline aluminosilicate zeolites as catalysts under the condition of gas phase in the presence of (a) lactone, (b) amine and/or ammonia and (c) water.
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- Method for preparing lactam
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The present invention is related to a method for preparing lactam represented by the following formula: wherein R is C2-10alkylene which may be optionally substituted with C1-6alkyl or phenyl; R′ is a hydrogen atom, C1-6alkyl, C1-6hydroxyalkyl or phenyl. The method for preparing lactam comprises an amination reaction using crystalline aluminosilicate zeolites as catalysts under the condition of gas phase in the presence of (a) lactone, (b) amine and/or ammonia and (c) water.
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- Novel 3-(2-adamantyl)pyrrolidines with potent activity against influenza A virus - Identification of aminoadamantane derivatives bearing two pharmacophoric amine groups
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The 3-(2-adamantyl)pyrrolidines 8a-g, 14 were synthesized and evaluated for activity against influenza A virus. The parent N-H compound 14 was several times more active than amantadine against H2N2 and H3N2 influenza A virus. The combined use of NMR spectroscopy and computational chemistry showed that the conformation around the pyrrolidine-adamantyl carbon-carbon bond is trans and the pyrrolidine heterocycle has an envelope conformation with C-2 out of the plane of the other ring atoms. N-Dialkylaminoethyl substitution of compound 14 resulted in the potent diamine analogues 8e,f,g. Interestingly, their lactam amine precursors were also active. Compounds 8e,f,g are the first adamantane derivatives, bearing two amine groups, reported to be active against influenza A virus.
- Stamatiou, George,Kolocouris, Antonios,Kolocouris, Nicolas,Fytas, George,Foscolos, George B,Neyts, Johan,De Clercq, Erik
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p. 2137 - 2142
(2007/10/03)
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- Cosmetic composition
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A composition suitable for topical application to mammalian skin or hair for inducing, maintaining or increasing hair growth comprises: (i) a first chemical inhibitor chosen from proteoglycanase inhibitors, glycosaminoglycanase inhibitors, glycosaminoglycan chain cellular uptake inhibitors or mixtures thereof; and (ii) a cosmetically acceptable vehicle for the chemical inhibitor; provided that when the first chemical inhibitor is a weak inhibitor, such that a 1 mM aqueous solution of the inhibitor reduces proteoglycanase activity, glycosaminoglycanase activity or cellular uptake of glycosaminoglycan chains, by from 5 to 50%, in accordance with at least one of the assay tests as herein described, then there is also present in the composition a second chemical inhibitor and/or an activity enhancer. When minoxidil is the sole chemical inhibitor, then the activity enhancer is a penetration enhancer chosen from a limited number of materials, including certain esters and cationic polymers. The total amount of chemical inhibitor present in the composition is sufficient to increase hair growth in the rat, when said composition is applied topically thereto, by at least 10% more than that obtainable using a control composition from which the said inhibitors have been omitted.
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- Cyclic amides as medicaments
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This invention provides a series of novel cyclic amides of formula I in which the group >Z--Y--XC=CH--NN-CH=CHC=N--NN--N=C and the other radicals have the meanings defined in the following specification. The compounds of formula I are leukotriene antagonists. The invention also provides pharmaceutically acceptable salts of the formula I compounds; pharmaceutical compositions containing the formula I compound, or their salts, for use in the treatment of, for example, allergic or inflammatory diseases, or endotoxic or traumatic shock conditions; and processs for the manufacture of the formula I compounds, as well as intermediates for use in such manufacture.
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- Method for the preparation of N-methyl and -N-ethyl-1-pyrrolidones
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The invention relates to a process for the preparation of a N-alkyl-2-pyrrolidone by reducing the corresponding N-(α-hydroxyalkyl)-2-pyrrolidone in the liquid phase under an atmosphere of hydrogen gas and in the presence of a noble metal hydrogenation catalyst while in the absence of trifluoroacetic acid.
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- Substituent Effects on the Product Distribution in Diazo Amide Photochemistry. Role of Ground-State Conformational Populations
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Effects of substituents on the photochemical processes of several α-diazo amides (1a-f) have been studied .Irradiation of 1b in ethyl ether and acetone afforded, in addition to a β-lactam, the reaction products with the solvents, ie., EtOCH2CONMe2 and 1,3-dioxolane, respectively, whereas similar irradiation of 1a in these solvents gave only intramolecular reaction products, ie., β- and γ-lactams.Displacement of oneof the alkyl groups on the amide nitrogen with a Ph group markedly changed its photochemical processes.Thus irradiations of 1c and 1d in MeOH gave oxindole almost exclusively.Introduction of an acetyl group on the diazo carbon also caused a change in the product distributions.Photolysis of 1e in methanol gave, for exaple, the Wolff rearrangement (WR) product of Me migration and a β-lactam, whereas similar irradiation of 1f afforded WR product and oxindole.The results are interpreted as indicating that the β-lactam, the oxindole, and the WR product are derived from the excited singlet state of s-Z form of the diazo amide itself, whereas that of s-E form dissociates nitrogen to generate singlet carbene, and that populations of each conformers in the ground state are important in determining the photochemical processes of the α-diazo amide.
- Tomioka, Hideo,Kondo, Masato,Izawa, Yasuji
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p. 1090 - 1094
(2007/10/02)
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