- Photocatalytic tandem reaction of primary alcohols with arylamines in the synthesis of amides and alkylquinolines in the presence of a heterogeneous Fe(CrO2)2–TiO2/X system under aerobic conditions
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A heterogeneous system Fe(CrO2)2–TiO2/X (where X is promoter NiO, CuO, ZnO, Cr2O3, Fe2O3, PrOCl, TbOCl, LaOCl, or EuOCl) was prepared. The photocatalytic activity of the system was tested in the tandem reaction of primary alcohols (BnOH, EtOH) with arylamines aimed at synthesizing benzamides and substituted 2-methylquinolines under aerobic conditions at room temperature.
- Makhmutov
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Read Online
- Metal-Free Oxidative B?N Coupling of nido-Carborane with N-Heterocycles
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A general method for the oxidative substitution of nido-carborane (7,8-C2B9H12?) with N-heterocycles has been developed by using 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) as an oxidant. This metal-free B?N coupling strategy, in both inter- and intramolecular fashions, gave rise to a wide array of charge-compensated, boron-substituted nido-carboranes in high yields (up to 97 %) with excellent functional-group tolerance under mild reaction conditions. The reaction mechanism was investigated by density-functional theory (DFT) calculations. A successive single-electron transfer (SET), B?H hydrogen-atom transfer (HAT), and nucleophilic attack pathway is proposed. This method provides a new approach to nitrogen-containing carboranes with potential applications in medicine and materials.
- Yang, Zhongming,Zhao, Weijia,Liu, Wei,Wei, Xing,Chen, Meng,Zhang, Xiao,Zhang, Xiaolei,Liang, Yong,Lu, Changsheng,Yan, Hong
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supporting information
p. 11886 - 11892
(2019/07/18)
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- C-Bridged Bispyrrolidines and Bispiperidines as New Ligands
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The preparation of methylene-bridged C2-symmetric nitrogen-heterocycles as a new class of ligands is described, including methylene-bridged pyridines, quinolones, piperidines and pyrrolidines. These methylene-bridged aromatic systems are obtained via a microwave assisted Ziegler-type reaction. The separation of diastereomers and the application of the copper complexes of these ligands for cyclopropanation reactions proves the applicability of these new types of ligands.
- Stumpf, Tim-Daniel J.,Steinbach, Manfred,H?ltke, Magdalene,Heuger, Gerold,Grasemann, Franka,Fr?hlich, Roland,Schindler, Siegfried,G?ttlich, Richard
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p. 5538 - 5547
(2018/10/25)
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- Deracemization of Phenyl-Substituted 2-Methyl-1,2,3,4-Tetrahydroquinolines by a Recombinant Monoamine Oxidase from Pseudomonas monteilii ZMU-T01
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A monoamine oxidase (MAO5) from Pseudomonas monteilii ZMU-T01 was first heterologously expressed in Escherichia coli BL21(DE3) and then used as a biocatalyst for the deracemization of racemic 2-methyl-1,2,3,4-tetrahdroquinoline derivatives to yield the unreacted R enantiomer with up to >99 % ee. Sequence alignment revealed that MAO5 shared 14.7 % identity toward the well-studied monoamine oxidase (MAO-N).
- Deng, Guozhong,Wan, Nanwei,Qin, Lei,Cui, Baodong,An, Miao,Han, Wenyong,Chen, Yongzheng
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p. 2374 - 2377
(2018/04/19)
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- Fe(CrO2)2-catalyzed, photoactivated oxidative one-pot tandem synthesis of substituted quinolines from primary alcohols and arylamines
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[Figure not available: see fulltext.] A one-pot tandem synthesis of substituted quinolines involving selective catalytic oxidation of primary alcohols to the corresponding aldehydes and their subsequent condensation with arylamines has been developed. Fe(CrO2)2 has been used as a catalyst, and oxidation has been performed with aqueous H2O2. To accelerate the catalytic oxidation of alcohols, photoactivation method has been applied.
- Makhmutov, Aynur R.,Mustafin, Akhat G.,Usmanov, Salavat M.
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p. 369 - 374
(2018/05/28)
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- One-Pot Oxidative Synthesis of Substituted Quinolines from Alcohols and Arylamines Catalyzed by Fe(CrO2)2 in Water Medium
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One-pot tandem synthesis was developed for substituted quinolines (in up to 97% yields) involving a selective catalytic oxidation of primary amines to aldehydes and their condensation with arylamines under the action of a dispersion of Fe(CrO2)2 and water solution of H2O2 at room temperature. The stage of catalytic oxidation of alcohols was accelerated by photoactivation. A presumable mechanism of the photoactivated tandem synthesis of 2-methylquinoline was suggested. Catalyst Fe(CrO2)2 was prepared by photochemical synthesis.
- Makhmutov
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p. 1166 - 1172
(2018/10/24)
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- Traceless Directing-Group Strategy in the Ru-Catalyzed, Formal [3 + 3] Annulation of Anilines with Allyl Alcohols: A One-Pot, Domino Approach for the Synthesis of Quinolines
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A unique, ruthenium-catalyzed, [3 + 3] annulation of anilines with allyl alcohols in the synthesis of substituted quinolines is reported. The method employs a traceless directing group strategy in the proximal C-H bond activation and represents a one-pot Domino synthesis of quinolines from anilines.
- Kumar, Gangam Srikanth,Kumar, Pravin,Kapur, Manmohan
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supporting information
p. 2494 - 2497
(2017/05/24)
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- Assembly of Diversely Substituted Quinolines via Aerobic Oxidative Aromatization from Simple Alcohols and Anilines
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An aerobic oxidative aromatization of simple aliphatic alcohols and anilines under the Pd(OAc)2/2,4,6-Collidine/Br?nsted acid catalytic system has been established, providing a direct approach for the preparation of diverse substituted quinoline derivatives in high yields with wide functional group tolerance. Practically, the protocol can be easily scaled up to gram-scale and was utilized in the concise formal synthesis of a promising herbicide candidate.
- Li, Jixing,Zhang, Jinlong,Yang, Huameng,Jiang, Gaoxi
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supporting information
p. 3284 - 3290
(2017/03/23)
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- Preparation method of quinoline derivative
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The invention provides a preparation method of a quinoline derivative. The method includes the steps of: in the presence of an oxidizing agent, adding a catalyst, then adding aniline or aromatic amine with different substituents, at the same time adding alcohol for reaction so as to prepare the quinoline derivative by one step. Specifically, the catalyst comprises a metal catalyst, an assistant catalyst I and an assistant catalyst II; the metal catalyst is a transition metal catalyst; the assistant catalyst I is an alkaline nitrogen-containing ligand; and the assistant catalyst II is an acidic compound. The quinoline derivative prepared by the method provided by the invention has stable performance and high purity. And the preparation method of the quinoline derivative can prepare quinoline, 2-methylquinoline, 8-hydroxyquinoline quinoline and other derivatives by one-step reaction, and the preparation method is simple and practicable. The preparation process does not produce new "three wastes", is environment-friendly, and provides a green and environment-friendly synthesis method. The preparation method has the characteristics of few raw material variety, little reaction equipment, few preparation step and low cost, and is more suitable for industrial production.
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Paragraph 0085; 0086
(2017/06/02)
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- Synthesis of quinolines and naphthyridines: Via catalytic retro-aldol reaction of β-hydroxyketones with ortho -aminobenzaldehydes or nicotinaldehydes
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A Cu(i)-catalyzed retro-aldol reaction of β-hydroxyketones with ortho-aminobenzaldehydes and nicotinaldehydes is reported that produces a range of quinolines and naphthyridines with high efficiency and selectivity. This reaction uses β-hydroxyketones as a regiospecific ketone-protected enolate source via copper-catalyzed retro-aldol Cα-Cβ bond cleavage. The in situ generated copper enolate undergoes kinetically favorable cyclization with ortho-amino aryl aldehydes to produce quinolines and naphthyridines in a chemo- and regioselective manner. The mild and weakly basic reaction conditions also suppress possible side reactions of benzaldehydes under strongly basic conditions, resulting in improved reaction yields.
- Zhang, Song-Lin,Deng, Zhu-Qin
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p. 8966 - 8970
(2016/10/05)
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- Quinolines synthesis by reacting 1,3-butanediol with anilines in the presence of iron catalysts
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2-, 4-, 6-, 7-, and 8-substituted quinolines were synthesized in 78–95% yield by the reaction of 1,3- butanediol with anilines in the presence of iron catalysts in carbon tetrachloride.
- Khusnutdinov,Bayguzina,Aminov
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p. 1613 - 1618
(2016/08/26)
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- Quinoline Synthesis by the Reaction of Anilines with 1,2-diols Catalyzed by Iron Compounds
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The synthesis of quinoline derivatives by cyclocondensation of anilines with 1,2-ethanediol, 1,2-propanediol, and 1,2-butanediol in the presence of iron-containing catalysts was performed for the first time.
- Khusnutdinov, Ravil,Bayguzina, Alfiya,Aminov, Rishat,Dzhemilev, Usein
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supporting information
p. 1022 - 1029
(2016/07/28)
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- Synthesis of substituted quinolines by the reaction of anilines with alcohols and CCl4 in the presence of Fe-containing catalysts
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Substituted quinolines were synthesized by the reaction of aniline derivatives with aliphatic alcohols and CCl4 upon the action of the FeCl3·6H2O catalyst.
- Khusnutdinov,Bayguzina,Aminov
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p. 133 - 137
(2013/11/19)
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- Facile synthesis of 2-methylquinolines from anilines on mesoporous N-doped TiO2 under UV and visible light
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Nitrogen-doped TiO2 was synthesized by a simple wet method using a nitrogen precursor hydrazine hydrate and nano TiO2. This photocatalyst was characterized by X-ray diffraction, highresolution transmission electron microscopy, diffused reflectance spectra, photoluminescence, and X-ray photoelectron spectroscopy. XPS analysis indicates the incorporation of anionic nitrogen in TiO2 lattice as O-Ti-N linkage. N2 adsorption-desorpion isotherm indicates the mesoporous nature of N-TiO2 with the surface area 130.0 m2/g. Sizes of N-TiO2 particles are found to be in the range of 5-30 nm by HRTEM images. DRS spectra reveal the extended absorption to the visible range. N-TiO2 is found to be more efficient than Ag-TiO2, Au-TiO2, and Pt-TiO2 in quinaldine synthesis under visible light. Copyright Taylor & Francis Group, LLC.
- Selvam,Swaminathan
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p. 500 - 508
(2013/05/21)
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- Nano Pt-TiO2 for an efficient one-pot photocatalytic synthesis of quinaldines from anilines and ethanol
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Nanosized platinum particles loaded on the TiO2 nanoparticles were prepared to assess its photocatalytic activity in simple one-pot synthesis of quinaldines from anilines in ethanol using UV light. The catalyst was characterized by X-ray diffra
- Selvam, Kaliyamoorthy,Sreedhar, Bojja,Swaminathan, Meenakshisundaram
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experimental part
p. 761 - 773
(2012/08/07)
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- Assembly of substituted 2-alkylquinolines by a sequential palladium-catalyzed Ci-N and Ci-C bond formation
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Diversity: A range of substituted 2-alkylquinolines can be prepared in a general and efficient synthetic approach that employs mild reaction conditions (see scheme). The synthesis is based on a sequential palladium-catalyzed Ci-N and Ci-C bond formation, followed by palladium-catalyzed aromatization, and results in the formation of the desired compounds in one step. Copyright
- Matsubara, Yoshio,Hirakawa, Saori,Yamaguchi, Yoshihiro,Yoshida, Zen-Ichi
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experimental part
p. 7670 - 7673
(2011/10/05)
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- Limitations of the two-phase doebner-miller reaction for the synthesis of quinolines
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The Doebner-Miller synthesis of quinolines under modified biphasic conditions was investigated. Crotonaldehyde, reacted readily with aniline to produce 2-methylquinoline. However, cinnamaldehyde and other γ-substituted α,β-unsaturated aldehydes yielded complex mixtures with substituted anilines to provide only trace quantities of quinolines. The Doebner-Miller reaction under these conditions is only suitable for sterically accessible α,β-unsaturated aldehydes.
- Reynolds, Kristie A.,Young, David J.,Loughlin, Wendy A.
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experimental part
p. 3645 - 3648
(2010/12/19)
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- Au-doped TiO2 nanoparticles for selective photocatalytic synthesis of quinaldines from anilines in ethanol
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A convenient eco-friendly photocatalytic synthesis of quinaldines has been developed by a simple one-pot reaction of anilines in ethanol solution with Au-loaded TiO2 under UV irradiation. Upon irradiation in the presence of Au-TiO2, aniline and oxidation products derived from ethanol undergo condensation-cyclization to afford quinaldines.
- Selvam,Swaminathan
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scheme or table
p. 4911 - 4914
(2010/10/02)
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- Design, synthesis, and evaluation in vitro of quinoline-8-carboxamides, a new class of poly(adenosine-diphosphate-ribose)polymerase-1 (PARP-1) inhibitor
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Poly(ADP-ribose)polymerase-1 is an important target enzyme in drug design; inhibitors have a wide variety of therapeutic activities. A series of quinoline-8-carboxamides was designed to maintain the required pharmacophore conformation through an intramolecular hydrogen bond. 3-Substituted quinoline-8-carboxamides were synthesized by Pd-catalyzed couplings (Suzuki, Sonogashira, Stille) to 3-iodoquinoline-8-carboxamide, an efficient process that introduces diversity in the final step. 2-Substituted quinoline-8-carboxamides were prepared by selective Pd-catalyzed couplings at the 2-position of 2,8-dibromoquinoline, followed by lithium-bromine exchange of the intermediate 2-(alkyl/aryl)-8-bromoquinolines and reaction with trimethylsilyl isocyanate. The intramolecular hydrogen bond was confirmed by X-ray and by NMR. The SAR of the 3-substituted compounds for inhibition of human recombinant PARP-1 activity showed a requirement for a small narrow group. Substituents in the 2-position increased potency, with the most active 2-methylquinoline-8-carboxamide having IC50 = 500 nM (IC50 = 1.8 μM for 5-aminoisoquinolin-1- one (5-AIQ, a standard water-soluble inhibitor)).
- Lord, Anna-Marie,Mahon, Mary F.,Lloyd, Matthew D.,Threadgill, Michael D.
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supporting information; experimental part
p. 868 - 877
(2009/11/30)
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- CAN-catalyzed three-component reaction between anilines and alkyl vinyl ethers: stereoselective synthesis of 2-methyl-1,2,3,4-tetrahydroquinolines and studies on their aromatization
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The CAN-catalyzed reaction between anilines and vinyl ethers at room temperature provides a convenient and efficient access to?4-alkoxy-2-methyl-1,2,3,4-tetrahydroquinolines. This reaction is stereoselective, favouring a cis arrangement for the alkoxy and methyl groups, and involves a three-component process that leaves a molecule of alcohol as the only side product. 2-Methylquinoline derivatives were efficiently prepared from 4-alkoxy-2-methyl-1,2,3,4-tetrahydroquinolines by Pd-C-promoted dehydrogenation.
- Sridharan, Vellaisamy,Avenda?o, Carmen,Menéndez, J. Carlos
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p. 673 - 681
(2007/10/03)
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- One-pot synthesis of substituted quinolines by iridium-catalyzed three-component coupling reaction
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A convenient and efficient synthesis of substituted quinolines in a simple one-pot reaction of an arylamine 1, an aromatic aldehyde or aliphatic aldehyde 2 and an aliphatic aldehyde 3 in the presence of transition metal complexes or Lewis acids was developed. Among them, the iridium catalyst [Ir(cod)Cl] 2 catalyzed the reaction most efficiently. Copyright
- Igarashi, Takeyuki,Inada, Takashi,Sekioka, Tadao,Nakajima, Takayuki,Shimizu, Isao
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p. 106 - 107
(2007/10/03)
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- Novel N-acylated heterocycles
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Described are compositions comprising a muscarinic receptor antagonist and an N-acylated heterocycle derivative having affinity for serotonergic receptors, and enantiomers, diastereoisomers, N-oxides, polymorphs, solvates and pharmaceutically acceptable salts thereof. The combination of a muscarinic receptor antagonist and an N-acylated heterocycle, or an enantiomer, diastereoisomer, N-oxide, polymorph, solvate or pharmaceutically acceptable salt thereof, is useful in the treatment of patients with neuromuscular dysfunction of the lower urinary tract and diseases related to 5-HT1A receptors.
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- The Rhodium Complex-catalyzed Synthesis of Quinolines from Aminoarenes and Aliphatic Aldehydes
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A variety of aminoarenes react with aliphatic aldehydes in the presence of a catalytic amount of a rhodium complex and an excess amount of the corresponding nitroarenes at 180 deg C to give 2-alkyl- and 2,3-dialkyl-substituted quinolines in excellent yields.Among the rhodium complexes examined, 2 exhibits the highest activity as a catalyst.Thus, 2-methyl-, 2-ethyl-3-methyl-, 2-propyl-3-ethyl-, 2-butyl-3-propylquinoline derivatives are readily obtained from aminoarenes and ethanal, propanal, butanal, and pentanal respectively.
- Watanabe, Yoshihisa,Shim, Sang Chul,Mitsudo, Take-aki
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p. 3460 - 3465
(2007/10/02)
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- Rhodium(I) Complexes of 8-Methyl-, 8-Ethyl-, and 8-Isopropyl-quinolines and Realated 2-Substituted Derivatives
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The complexes have been prepared from on adding unidentate L (8-methyl-, -ethyl-, or -isopropyl-quinoline) or bidentate L (1,10-phenantroline or quinoline-2-carboxaldehide-N-methylimine). 8-Alkyl-substitution of the latter ligand gives the complexes as isomers with uni- and bi-dentate L respectively with relative stabilities of the unidentate form depending on the 8-substituent in the order Pri > Et > Me.Unidentate L is also favoured by replacing PPh3 by P(C6H11)3 but bidentate co-ordination is found using AsPh3 or PMe2Ph.Equilibrium constants for chloro-bridge cleavage of by 8-substituted and 2,8-disubstituted quinolines are reduced by increasing the size of the 8-susbtituent and even more by further introduction of a 2-methyl group.The contributions of distortions in the co-ordination to these changes in equilibrium constants are discussed.
- Deeming, Antony J.,Rothwell, Ian P.
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p. 1259 - 1264
(2007/10/02)
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