- 8-Hydroxyquinolin-2(1H)-one analogues as potential β2-agonists: Design, synthesis and activity study
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β2-Agonists that bind to plasmalemmal β2-adrenoceptors causing cAMP accumulation are widely used as bronchodilators in chronic respiratory diseases. Here, we designed and synthesized a group of 8-hydroxyquinolin-2(1H)-one analogues and studied their β2-agonistic activities with a cellular cAMP assay. Compounds B05 and C08 were identified as potent (EC50 2-agonists among the compounds tested. They behaved as partial β2-agonists in non-overexpressed HEK293 cells, and possessed rapid smooth muscle relaxant actions and long duration of action in isolated guinea pig tracheal strip preparations. In summary, B05 and C08 are β2-agonists with potential applicability in chronic respiratory diseases.
- Xing, Gang,Zhi, Zhengxing,Yi, Ce,Zou, Jitian,Jing, Xuefeng,Yiu-Ho Woo, Anthony,Lin, Bin,Pan, Li,Zhang, Yuyang,Cheng, Maosheng
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- Decarboxylation-triggered homo-Nazarov cyclization of cyclic enol carbonates catalyzed by rhenium complex
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Decarboxylative homo-Nazarov cyclization catalyzed by a Lewis acid was achieved using a cyclic enol carbonate bearing a cyclopropane moiety as a substrate. Various substrates were converted into the corresponding multi-substituted cyclohexenones in good yieldsviadecarboxylation, followed by 6-membered ring formation involving cyclopropane-ring-opening.
- Kimaru, Natsuki,Komatsuki, Keiichi,Saito, Kodai,Yamada, Tohru
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supporting information
p. 6133 - 6136
(2021/06/30)
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- Design, synthesis, and molecular docking study of novel quinoline-based bis-chalcones as potential antitumor agents
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A novel series of quinoline-based symmetrical and unsymmetrical bis-chalcones was synthesized via a Claisen–Schmidt condensation reaction between 3-formyl-quinoline/quinolone derivatives with acetone or arylidene acetones, respectively, by using KOH/MeOH/H2O as a reaction medium. Twelve of the obtained compounds were evaluated for their in vitro cytotoxic activity against 60 different human cancer cell lines according to the National Cancer Institute protocol. Among the screened compounds, the symmetrical N-butyl bis-quinolinyl-chalcone 14g and the unsymmetrical quinolinyl-bis-chalcone 17o bearing a 7-chloro-substitution on the N-benzylquinoline moiety and 4-hydroxy-3-methoxy substituent on the phenyl ring, respectively, exhibited the highest overall cytotoxicity against the evaluated cell lines with a GI50 range of 0.16–5.45 μM, with HCT-116 (GI50 = 0.16) and HT29 (GI50 = 0.42 μM) (colon cancer) representing best-case scenarios. Notably, several GI50 values for these compounds were lower than those of the reference drugs doxorubicin and 5-FU. Docking studies performed on selected derivatives yielded very good binding energies in the active site of proteins that participate in key carcinogenic pathways.
- Insuasty, Daniel,García, Stephanie,Abonia, Rodrigo,Insuasty, Braulio,Quiroga, Jairo,Nogueras, Manuel,Cobo, Justo,Borosky, Gabriela L.,Laali, Kenneth K.
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- Polysubstituted Indole Synthesis via Palladium/Norbornene Cooperative Catalysis of Oxime Esters
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Polysubstituted indoles are prevalent in pharmaceuticals, agrochemicals, and organic materials. Presented herein is the fact that polyfunctionalized indoles can be efficiently constructed from easily accessible oxime esters and aryl iodides, involving a palladium/norbornene synergistic synthesis. The reaction is enabled by a unique class of electrophiles in palladium/norbornene cooperative catalysis, which are oxime esters derived from simple ketone. The broad substrate scope and high functional group tolerance could make this method attractive for the synthesis of polysubstituted indoles.
- Huang, Liangbin,Jiang, Huanfeng,Lin, Haojiang,Liu, Jiechun
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supporting information
(2022/01/20)
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- Inhibition of Autophagy by a Small Molecule through Covalent Modification of the LC3 Protein
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The autophagic ubiquitin-like protein LC3 functions through interactions with LC3-interaction regions (LIRs) of other autophagy proteins, including autophagy receptors, which stands out as a promising protein–protein interaction (PPI) target for the intervention of autophagy. Post-translational modifications like acetylation of Lys49 on the LIR-interacting surface could disrupt the interaction, offering an opportunity to design covalent small molecules interfering with the interface. Through screening covalent compounds, we discovered a small molecule modulator of LC3A/B that covalently modifies LC3A/B protein at Lys49. Activity-based protein profiling (ABPP) based evaluations reveal that a derivative molecule DC-LC3in-D5 exhibits a potent covalent reactivity and selectivity to LC3A/B in HeLa cells. DC-LC3in-D5 compromises LC3B lipidation in vitro and in HeLa cells, leading to deficiency in the formation of autophagic structures and autophagic substrate degradation. DC-LC3in-D5 could serve as a powerful tool for autophagy research as well as for therapeutic interventions.
- Chen, Kaixian,Chen, Zhifeng,Dang, Yongjun,Ding, Hong,Fan, Shijie,Hu, Junchi,Jiang, Hualiang,Li, Lianchun,Li, Quanfu,Lin, Tingting,Lu, Junyan,Luo, Cheng,Otomo, Chinatsu,Otomo, Takanori,Tan, Minjia,Tao, Hongru,Wan, Wei,Wen, Yi,Xie, Yuli,Xu, Pan,Yao, Zhiyi,Yue, Liyan,Zhang, Bidong,Zhang, Naixia,Zhang, Yuanyuan,Zhou, Bing,Zhu, Mingrui
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supporting information
p. 26105 - 26114
(2021/11/09)
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- NOVEL SMALL MOLECULES THAT BIND AND/OR MODULATE DIFFERENTFORMS OF TAU OLIGOMERS
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The present invention relates to novel small molecules of Formulas I, II, III, Ilia, Illb, and IV and pharmaceutically acceptable salts thereof, as well as the preparation and the use thereof.
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Page/Page column 34; 35
(2020/11/03)
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- Iron(ii)-folded single-chain nanoparticles: a metalloenzyme mimicking sustainable catalyst for highly enantioselective sulfa-Michael addition in water
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Metalloenzyme is a source of inspiration for chemists who attempt to create versatile synthetic catalysts for aqueous catalysis. Herein, we impart metalloenzyme-like characteristics to a chiral FeII-oxazoline complex by incorporating an Fe(ii) ion into a chiral oxazoline-containing discrete self-folded polymer, to realize highly enantioselective sulfa-Michael addition (SMA) in water. Intrachain FeII-oxazoline complexation together with hydrophobic interactions triggers the self-folding of the oxazoline-containing single polymeric chain in water. The formed FeII-folded single-chain polymeric nanoparticles (SCPNs) significantly accelerate the aqueous asymmetric SMA reaction via a self-folded hydrophobic compartment around the catalytic sites, reminiscent of metalloenzymatic catalysis. In addition, they can be facilely recovered for reuse by simple thermo-controlled separation due to their thermo-responsive properties. Such metallo-folded SCPNs combine the benefits of transition metal- and bio-catalyst, and avoid the tedious procedures of separation, which is a benefit for energy-saving and industrial applications.
- Li, Chaoping,Li, Shiye,Tan, Rong,Wang, Jiajun,Wang, Weiying,Yin, Donghong
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supporting information
p. 4645 - 4655
(2020/08/10)
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- β-Carbolines: synthesis of harmane, harmine alkaloids and their structural analogs by thermolysis of 4-aryl-3-azidopyridines and investigation of their optical properties
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[Figure not available: see fulltext.] Interest in β-carbolines is caused by the biological activity of these compounds and the use of their fluorescent properties in the study of their interaction with DNA and other biological targets, as well as with drug delivery vehicles. A new general method for the synthesis of harmane, harmine, and their structural analogs by thermolysis of substituted 4-aryl-3-azidopyridines was developed, and their optical properties were studied.
- Shuvalov, Vladislav Yu.,Elisheva, Valeriya А.,Belousova, Anastasiya S.,Arshinov, Evgenii V.,Glyzdinskaya, Larisa V.,Vorontsova, Marina А.,Chernenko, Sergei А.,Fisyuk, Aleksander S.,Sagitullina, Galina P.
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- Selective Cross-Dehydrogenative C(sp3)-H Arylation with Arenes
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Selective C(sp3)-C(sp2) bond construction is of central interest in chemical synthesis. Despite the success of classic cross-coupling reactions, the cross-dehydrogenative coupling between inert C(sp3)-H and C(sp2)-H bonds represents an attractive alternative toward new C(sp3)-C(sp2) bonds. Herein, we establish a selective inter-and intramolecular C(sp3)-H arylation of alcohols with nondirected arenes that thereby provides a general pathway to access a wide range of β-arylated alcohols, including tetrahydronaphthalen-2-ols and benzopyran-3-ols, with high to excellent chemo-and regioselectivity.
- Hao, Hong-Yan,Mao, Yang-Jie,Xu, Zhen-Yuan,Lou, Shao-Jie,Xu, Dan-Qian
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supporting information
p. 2396 - 2402
(2020/03/13)
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- Design, synthesis and biological evaluation of novel diaryl pyrazole derivatives as anticancer agents
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Cancer is one of the major causes of mortality all around the world. Globally, nearly 1 in 6 deaths is due to cancer. Researchers are trying to synthesize new anticancer agents. Previous studies demonstrated that some pyrazole derivatives could be considered as potential anticancer agents. Herein, ten novel derivatives of 1,5-diarylpyrazole were synthesized in four step reactions and cytotoxic activity was investigated by MTT cell viability assay. All of the compounds were characterized by1H NMR and13C NMR and their purity was confirmed by elemental analysis. The cytotoxicity was determined against three cancerous cell lines (HT-29, U87MG and MDA-MB 468) and AGO1522 as a normal cell line. Compound 5a showed the best cytotoxic activity on cancerous cell lines in comparison to paclitaxel. Annexin V/ PI staining assay also showed that compounds 5a and 5i would lead to significant apoptosis induction in MDA-MB 486 cell line.
- Nourmahammadi, Jalal,Moghadam, Ebrahim Saeedian,Shahsavari, Zahra,Amini, Mohsen
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p. 216 - 223
(2020/02/29)
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- Boosting multiple photo-assisted and temperature controlled reactions with a single redox-switchable catalyst: Solvents as internal substrates and reducing agent
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An alternative and economically viable process for the synthesis of β-aryl enals, enones and the aryl amines has been developed by partial oxidation of ethanol, isopropanol and N, N-dimethyl formamide (DMF). The formation of β-aryl enals, enones and the aryl amines was catalyzed by a mixed metal oxides layer of cobalt and chromium supported on halloysite nanotubes, designated as CoCr2O4-HNT. The C[sbnd]C and C[sbnd]N bond formation reactions were found to be influenced by temperature and the nature of base. The condensation of aldehyde with in situ generated acetaldehyde by ethanol oxidation forming β-aryl enals occurred selectively at 120 °C. The partial oxidation of isopropanol to acetone and its condensation with aldehydes forming β-aryl enones occurred at room temperature. Increase in temperature caused the liberation of hydrogen gas from isopropanol and allowed the reversible reduction of aldehydes to alcohols. Increase in temperature in isopropanol and increase in base concentration in ethanol causes the selective reduction of aldehydes to alcohols. Besides being active for the Claisen-Schmidt type of reactions and the aryl halides amination process, the synthesized catalyst was also found to be highly active for the photocatalytic oxidation of benzyl alcohols in absence of any external oxidizing agent. The positive holes (h+) generated at the Co(II) site as evident from EPR analysis was considered to be responsible for high photocatalytic activity of the material reducing the recombination rate of holes and electrons (e?). Density Functional Theory calculations were performed to understand the mechanism of ethanol oxidation to acetaldehyde.
- Bania, Kusum K.,Baruah, Manash J.,Bhattacharyya, Pradip K.,Das, Biraj,Karunakar, Galla V.,Roy, Subhasish,Saikia, Lakshi,Saikia, Pinku,Sharma, Mukesh
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p. 104 - 121
(2020/06/01)
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- Iodine/water-mediated deprotective oxidation of allylic ethers to access α,β-unsaturated ketones and aldehydes
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The first iodine/water-mediated deprotective oxidation of allylic ethers to access α,β-unsaturated ketones and aldehydes was achieved. The reaction tolerates a wide range of functionalities. Furthermore, this protocol was found to be applicable to the oxidative transformation of allylic acetates. The proposed mechanism involves an oxygen transfer from solvent water to the carbonyl products.
- Chen, Weifeng,Jiang, Kezhi,Xue, Yuntian,Yan, Yaolong,Yang, Lei
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p. 14720 - 14724
(2020/04/27)
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- RhIII-Catalyzed Synthesis of Highly Substituted 2-Pyridones using Fluorinated Diazomalonate
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A RhIII-catalyzed strategy was developed for the rapid construction of highly substituted 2-pyridone scaffolds using α,β-unsaturated oximes and fluorinated diazomalonate. The reaction proceeds through direct, site-selective alkylation based on migratory insertion and subsequent cyclocondensation. A wide substrate scope with different functional groups was explored. The requirement of fluorinated diazomalonate was explored for this transformation. The developed methodology was further extended with the synthesis of the bioactive compound.
- Das, Debapratim,Sahoo, Gopal,Biswas, Aniruddha,Samanta, Rajarshi
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p. 360 - 364
(2020/01/25)
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- Heck Reactions of Acrolein or Enones and Aryl Bromides – Synthesis of 3-Aryl Propenals or Propenones and Consecutive Application in Multicomponent Pyrazole Syntheses
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3-(Hetero)aryl propenals or propenones are efficiently prepared by a Heck reaction of (hetero)aryl bromides and acrolein or vinyl ketones using Beller's CataCXium Ptb ligand under Jeffery's and Fu's conditions. The formation of these three-carbon building blocks is embedded into consecutive three- and pseudo-four-component syntheses of 3-(hetero)aryl and 3,5-diarylpyrazoles with a broad substitution pattern in moderate to excellent yield.
- Stephan, Marvin,Panther, Jesco,Wilbert, Fabio,Ozog, Pauline,Müller, Thomas J. J.
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supporting information
p. 2086 - 2092
(2020/03/23)
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- Use of a switchable-hydrophilicity solvent as both a solvent and a catalyst in aldol condensation
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A switchable-hydrophilicity solvent, N,N-dimethylcyclohexylamine, was used as a recyclable catalyst and solvent for aldol condensation, giving >97% pure product in 94% isolated yield without the need for purification or additional solvents. CO2-triggered separation produced yields greater than conventional workup and allowed facile recycling of the amine.
- Poole, Hailey,Gauthier, Jeremy,Vanderveen, Jesse R.,Jessop, Philip G.,Lee, Roland
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supporting information
p. 6263 - 6267
(2019/12/03)
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- Fe3O4?l-Proline/Pd nanocomposite for one-pot tandem catalytic synthesis of (±)-warfarin from benzyl alcohol: Synergistic action of organocatalyst and transition metal catalyst
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One-pot synthesis of (±)-warfarin, an anticoagulant, has been achieved from benzyl alcohol in a 'green way' by using a multicomponent catalyst. For the purpose, l-proline capped Fe3O4 nanoparticles (Fe3O4?l-proline NPs) were synthesized and metallic palladium was loaded on its surface (Fe3O4?l-proline/Pd NCs). The morphology, particle size and shape were studied by using FESEM and TEM analysis. The Pd present on the surface was responsible for oxidation of benzyl alcohol and its derivatives to the corresponding aldehyde in situ. This in turn, condensed with acetone to form the aldol condensation product, benzylideneacetone, at 70 °C due to the presence of the l-proline organocatalyst on the surface of Fe3O4 NPs. Later, 4-hydroxycoumarin was introduced to condense with in situ generated benzylideneacetone by a Michael addition to form the target product (±)-warfarin. It was established that benzyl alcohol can be converted into the final product, (±)-warfarin, with an overall 35% yield within 5 days in a single-pot process. This process requires a rise in temperature in stages to a maximum of 100 °C and 1 atm pressure of dioxygen gas. An important aspect of the developed process is the avoidance of loss of costly Pd by leaching and catalyst recovery by the use of a magnetic field. The use of a solvent like PEG-400 makes the process green in a true sense. The interaction of l-proline with Fe3O4 NPs and the presence of Pd on the surface were confirmed by the FTIR and XRD patterns, respectively. The present study hereby suggests a combined 3-step mechanism for the production of the target product warfarin. Pilot-scale one-pot production of (±)-warfarin was carried out and a flow diagram with various unit processes is presented.
- Tomer, Sanjiv O.,Soni, Hemant P.
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p. 6517 - 6531
(2019/11/20)
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- A class of polyene diketone antitumor compounds
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The invention provides a class of new polyene diketone compounds, wherein the new polyene diketone compounds have good free radical scavenging and antitumor activities, can be used for preparing antitumor drugs for treating humans or animals, has characteristics of low preparation cost and good achievability, and has a molecular structure formula defined in the specification.
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Paragraph 0053-0055
(2019/10/01)
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- Construction of Multiple-Substituted Chiral Cyclohexanes through Hydrogenative Desymmetrization of 2,2,5-Trisubstituted 1,3-Cyclohexanediones
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The construction of chiral multiple-substituted cyclohexanes motifs is a challenging topic in organic synthesis. By the combination of desymmetrization and remote stereocontrol, a ruthenium-catalyzed transfer hydrogenative desymmetrization of 2,2,5-trisubstituted 1,3-cyclohexanediones has been successfully developed for the construction of chiral multiple-substituted cyclohexanes with high enantioselectivity and diastereoselectivity. When an ester group was introduced to the two-position, a hydrogenative desymmetrization/transesterification cascade occurred, affording the bicyclic lactones bearing three stereocenters, including two discrete stereocenters and one quaternary stereogenic center, with high enantioselectivity. The products are the multiple-substituted chiral cyclohexanes bearing the hydroxyl and carbonyl functional groups, which provide a new opportunity for further precise elaboration.
- Yu, Chang-Bin,Song, Bo,Chen, Mu-Wang,Shen, Hong-Qiang,Zhou, Yong-Gui
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supporting information
p. 9401 - 9404
(2019/11/28)
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- Scalable Multicomponent Synthesis of (Hetero)aryl-Substituted Phenyls: Focus on Metal-Free Halogenated Biaryls, 3-Arylindoles, and Isourolithine A Synthesis
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In the context of the growing interest of the scientific community for the development of sustainable synthetic strategies to access aromatic structures, we present a practical and metal-free approach to (hetero)biaryls which exploits the advantages of multicomponent reactions in sustainable solvents. In situ acid-catalysed generation of (hetero)aryl acetoxy dienes from the corresponding (hetero)arylidene acetones in a metal vessel, followed by Diels-Alder reaction using an electron-poor alkyne as dienophile, delivers the expected aromatic products after final oxidation of the cycloadduct. This protocol has been demonstrated as a convenient alternative to the previously reported synthetic strategies, considering its scalability and environmental sustainability and the low cost of substrates and equipment. Moreover, it has been successfully applied to the metal-free regioselective synthesis of (hetero)aryl-substituted-phenyls, 2-unsubstituted-3-aryl-indoles, and to the total synthesis of isourolithine A.
- Temperini, Andrea,Lanari, Daniela,Colognese, Francesco,Piazzolla, Francesca
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p. 7711 - 7719
(2019/12/12)
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- Utilization of Synthetic Calcium-Phyllosilicates as Bifunctional Bases in the Matsuda-Heck Reaction
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Calcium-phyllosilicates can successfully be used as novel bases in the Matsuda-Heck reaction using methanol as solvent. The new experimental set-up distinguishes itself by higher reactivity and better selectivity compared to other systems.
- Brunner, Heiko,Vedder, Lennart
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p. 698 - 702
(2019/01/04)
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- Encapsulating mesoporous metal nanoparticles: Towards a highly active and stable nanoreactor for oxidative coupling reactions in water
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We design and prepare a highly active and stable nanoreactor via encapsulating various mesoporous metal nanoparticles with an amphiphilic hollow shell, which presents excellent performance in oxidative coupling reactions in water for efficient production of α,β-unsaturated ketones.
- Zou, Houbing,Dai, Jinyu,Wang, Runwei
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supporting information
p. 5898 - 5901
(2019/05/27)
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- Ligand-free palladium-catalyzed tandem pathways for the synthesis of 4,4-diarylbutanones and 4,4-diaryl-3-butenones under microwave conditions
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Two efficient Pd-catalyzed tandem pathways for the synthesis of 4,4-diaryl-2-butanones and 4,4-diaryl-3-buten-2-ones were elaborated. The first step in both procedures was the Heck coupling of methyl vinyl ketone (MVK) and various aryl iodides leading to 4-aryl-3-buten-2-one with the yield of up to 92% in 1?hr. The second step performed with the same catalyst and a new portion of aryl iodide in the presence K2CO3 as a base produced 4,4-diaryl-3-buten-2-ones in high yield. Reaction selectivity changed completely to saturated 4,4-diaryl-2-butanones, reductive Heck products, when a tertiary amine was used instead of K2CO3. Due to the application of microwave irradiation (MW), the desired products were obtained in high yield in a short time (4?hr), using 0.5?mol% of the Pd (OAc)2 catalyst without additional ligands.
- Wirwis, Anna,Trzeciak, Anna M.
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- Activation of anti-oxidant Nrf2 signaling by enone analogues of curcumin
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Inflammation and oxidative stress are common in many chronic diseases. Targeting signaling pathways that contribute to these conditions may have therapeutic potential. The transcription factor Nrf2 is a major regulator of phase II detoxification and anti-oxidant genes as well as anti-inflammatory and neuroprotective genes. Nrf2 is widespread in the CNS and is recognized as an important regulator of brain inflammation. The natural product curcumin exhibits numerous biological activities including ability to induce the expression of Nrf2-dependent phase II and anti-oxidant enzymes. Curcumin has been examined in a number of clinical studies with limited success, mainly owing to limited bioavailability and rapid metabolism. Enone analogues of curcumin were examined with an Nrf2 reporter assay to identify Nrf2 activators. Analogues were separated into groups with a 7-carbon dienone spacer, as found in curcumin; a 5-carbon enone spacer with and without a ring; and a 3-carbon enone spacer. Activators of Nrf2 were found in all three groups, many of which were more active than curcumin. Dose-response studies demonstrated that a range of substituents on the aromatic rings of these enones influenced not only the sensitivity to activation, reflected in EC50 values, but also the extent of activation, which suggests that multiple mechanisms are involved in the activation of Nrf2 by these analogues.
- Deck, Lorraine M.,Hunsaker, Lucy A.,Vander Jagt, Thomas A.,Whalen, Lisa J.,Royer, Robert E.,Vander Jagt, David L.
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supporting information
p. 854 - 865
(2017/12/13)
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- Evaluation of sulphonamide derivatives acting as inhibitors of human carbonic anhydrase isoforms I, II and Mycobacterium tuberculosis β-class enzyme Rv3273
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A series of novel sulphonamide derivatives was obtained from sulphanilamide which was N4-alkylated with ethyl bromoacetate followed by reaction with hydrazine hydrate. The hydrazide obtained was further reacted with various aromatic aldehydes. The novel sulphonamides were characterised by infrared, mass spectrometry, 1H- and 13C-NMR and purity was determined by high-performance liquid chromatography (HPLC). Human (h) carbonic anhydrase (CA, EC 4.2.1.1) isoforms hCA I and II and Mycobacterium tuberculosis β-CA encoded by the gene Rv3273 (mtCA 3) inhibition activity was investigated with the synthesised compounds which showed promising inhibition. The KIs were in the range of 54.6 nM–1.8 μM against hCA I, in the range of 32.1 nM–5.5 μM against hCA II and of 127 nM–2.12 μM against mtCA 3.
- Wani, Tanvi V.,Bua, Silvia,Khude, Pravin S.,Chowdhary, Abdul H.,Supuran, Claudiu T.,Toraskar, Mrunmayee P.
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p. 962 - 971
(2018/05/29)
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- Rh(III)-Catalyzed Enaminone-Directed Alkenyl C-H Activation for the Synthesis of Salicylaldehydes
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A Rh(III)-catalyzed enaminone-directed alkenyl C-H coupling with alkynes for the synthesis of salicylaldehyde derivatives is reported. This represents a unique example of benzene ring framework formation through a transition-metal-catalyzed, directed C-H activation strategy. The two incorporated reactive functionalities, aldehyde and hydroxy groups, provide convenient synthetic handles for further structural elaboration.
- Qi, Bing,Guo, Shan,Zhang, Wenjing,Yu, Xiaolong,Song, Chao,Zhu, Jin
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supporting information
p. 3996 - 3999
(2018/07/15)
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- Gram-scale preparation of dialkylideneacetones through Ca(OH)2-catalyzed Claisen-Schmidt condensation in dilute aqueous EtOH
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A synthetic method of dialkylideneacetones has been developed. Compared with known protocols, the method employed catalytic Ca(OH)2 as the cheap, mild base catalyst and dilute aqueous EtOH (20%, v/v) as the green and safe solvent. The procedure was easily operated: In most cases, the product could be isolated by a simple filtration, and purified by washing with water. This paper provided experimental details of the reactions, which could be applied in gram-scale synthesis and should be a very reliable and practical protocol to prepare these useful compounds in laboratory and at the industrial level.
- Zhang, Hao,Han, Mengting,Yang, Chenggen,Yu, Lei,Xu, Qing
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- An Adverse Effect of Higher Catalyst Loading and Longer Reaction Time on Enantioselectivity in an Organocatalytic Multicomponent Reaction
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An enantioselective organocatalytic multicomponent reaction of aldehydes, ketones, and Meldrum's acid has been developed. A cinchona-based primary amine (1 mol %) catalyses the multicomponent reaction via the formation of the Knoevenagel product and a chiral enamine to form enantiopure δ-keto Meldrum's acids in a tandem catalytic pathway. An adverse effect of higher catalyst loading and longer reaction time on enantioselectivity was studied. This mild protocol provides an easy access to enantiopure carboxylic acids, esters and amides and the method is scalable on a gram quantity. DFT calculations were carried out on the proposed reaction mechanism and they were in close agreement with the experimental results.
- Khopade, Tushar M.,Mete, Trimbak B.,Arora, Jyotsna S.,Bhat, Ramakrishna G.
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p. 6036 - 6040
(2018/04/27)
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- Dehydrogenative Formation of Resorcinol Derivatives Using Pd/C-Ethylene Catalytic System
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The conversion of substituted 1,3-cyclohexanediones to the alkyl ethers of resorcinol using a Pd/C-ethylene system is reported. In these reactions, ethylene works as a hydrogen acceptor. The efficient synthesis of resveratrol was achieved using this protocol as a key step. In addition, the direct formation of substituted resorcinols was carried out by adding K2CO3 into the reaction media.
- El-Deeb, Ibrahim Yussif,Funakoshi, Tatsuya,Shimomoto, Yuya,Matsubara, Ryosuke,Hayashi, Masahiko
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p. 2630 - 2640
(2017/03/14)
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- Hydroxytrifluoromethylation of Alkenes Using Fluoroform-Derived CuCF3
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Hydroxytrifluoromethylation of alkenes using the fluoroform (CF3H)-derived [CuCF3] reagent is described. In the presence of additive B2Pin2 and air, this reagent effectively facilitates the addition of hydroxy and trifluoromethyl groups across an alkene double bond, a formal hydroxytrifluoromethylation process. Various β-trifluoromethyl alcohols can be synthesized from simple alkenes where the ultimate CF3 source is the industrial byproduct fluoroform.
- Yang, Xinkan,He, Lisi,Tsui, Gavin Chit
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supporting information
p. 2446 - 2449
(2017/05/12)
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- Palladium-Catalyzed Cleavage of α-Allenylic Aryl Ether toward Pyrazolemethylene-Substituted Phosphinyl Allenes and Their Transformations via Alkenyl C-P(O) Cleavage
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A palladium-catalyzed two-component coupling of allenylphosphine oxides with conjugated N-tosylhydrazones is revealed. For the first time, the cleavage of α-allenylic aryl ether toward pyrazolemethylene-substituted phosphinyl allenes enabled facile synthesis of combined motifs with pyrazole and allene. Moreover, the obtained adducts could be easily transformed to potential bioactive multifunctionalized phosphinates via a novel alkenyl C-P(O) cleavage.
- Zhu, Jie,Mao, Mao,Ji, Huan-Jing,Xu, Jiang-Yan,Wu, Lei
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supporting information
p. 1946 - 1949
(2017/04/28)
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- Discovery of curcumin inspired sulfonamide derivatives as a new class of carbonic anhydrase isoforms I, II, IX, and XII inhibitors
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A series of curcumin inspired sulfonamide derivatives was prepared from various chalcones and 4-sulfamoyl benzaldehyde via Claisen–Schmidt condensation. All new compounds were assayed as inhibitors of four human isoforms of the metalloenzyme carbonic anhydrase (hCA, EC 4.2.1.1) isoforms hCA I, II, IX and XII. Interesting inhibitory activities were observed against all these isoforms. hCA I, an isoform involved in several eye diseases was inhibited moderately with KIs in the range of 191.8–904.2 nM, hCA II, an antiglaucoma drug target was highly inhibited by the new sulfonamides, with KIs in the range of 0.75–8.8 nM. hCA IX, a tumor-associated isoform involved in cancer progression and metastatic spread was potently inhibited by the new sulfonamides, with KIs in the range of 2.3–87.3 nM, whereas hCA XII, and antiglaucoma and anticancer drug target, was inhibited with KIs in the range of 6.1–71.8 nM. It is noteworthy that one of the new compounds, 5d, was found to be almost 9 times more selective against hCA II (KI = 0.89 nM) over hCA IX and hCA XII, whereas 5e was 3 and 70 times more selective against hCA II (KI = 0.75 nM) over hCA IX and hCA XII, respectively.
- Ramya, P. V. Sri,Angapelly, Srinivas,Angeli, Andrea,Digwal, Chander Singh,Arifuddin, Mohammed,Babu, Bathini Nagendra,Supuran, Claudiu T.,Kamal, Ahmed
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p. 1274 - 1281
(2017/10/09)
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- Multifunctional supported bimetallic catalysts for a cascade reaction with hydrogen auto transfer: Synthesis of 4-phenylbutan-2-ones from 4-methoxybenzyl alcohols
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We report the one-pot tandem synthesis of 4-(4-methoxyphenyl)butan-2-one directly from 4-methoxybenzyl alcohol and acetone using a multifunctional supported AuPd nanoalloy catalyst. This one-pot synthesis involves dehydrogenation, aldol condensation and hydrogenation of CC. In this supported AuPd catalyst, the bimetallic sites catalyse the dehydrogenation and hydrogenation steps and, in combination with the support, catalyse the C-C coupling (aldol) process. This supported bimetallic catalyst is also effective in utilizing hydrogen from the dehydrogenation reaction for the hydrogenation of 4-(4-methoxyphenyl)but-3-en-2-one to 4-(4-methoxyphenyl)butane-2-one via a hydrogen auto transfer route. These multifunctional catalysts were characterised using transmission electron microscopy, X-ray diffraction and X-ray photoelectron spectroscopy.
- Morad, Moataz,Nowicka, Ewa,Douthwaite, Mark,Iqbal, Sarwat,Miedziak, Peter,Edwards, Jennifer K.,Brett, Gemma L.,He, Qian,Morgan, David,Alshammari, Hamed,Bethell, Donald,Knight, David W.,Sankar, Meenakshisundaram,Hutchings, Graham J.
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p. 1928 - 1936
(2017/07/15)
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- A method of preparing alpha,beta-unsaturated ketones
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The invention relates to a method of preparing alpha,beta-unsaturated ketones. The method is characterized by comprising steps of (1) adding a copper catalyst and an alkali into a reaction tube, adding a liquid mixture of a solvent and reactants which are a beta-hydroxy ketone and an aromatic aldehyde under nitrogen protection into the reaction tube and reacting the mixture; (2) performing filtration, extraction, drying, and low-pressure solvent removing after the reaction is finished to obtain an alpha,beta-unsaturated ketone crude product; and (3) performing separation and purification to obtain an alpha,beta-unsaturated ketone product. A copper enolate is generated in situ through a retrograde aldol condensation reaction and is further subjected to aldol condensation with the aromatic aldehyde to obtain the final product. The beta-hydroxy ketone and the aromatic aldehyde are injected through injectors under nitrogen protection, and the reaction is performed under stirring in an oil bath pot having a temperature of 25-120 DEG C for 3-8 h. The method has characteristics of mild conditions, simple operation, easily available raw materials, and environment protection and is hopped to be widely applied in the fine chemical synthesis fields such as medicine intermediates, perfume and pesticides.
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Paragraph 0034; 0035; 0036; 0037; 0038
(2017/07/15)
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- Method for preparing alpha and beta-unsaturated ketone
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The invention provides a method for preparing alpha and beta-unsaturated ketone. The method includes that L-proline is used as a catalyst, secondary amine is used as a cocatalyst, and the alpha and beta-unsaturated ketone can be directly synthesized in alcohol or ketone solution by means of aldol condensation under neutral conditions at one step. Compared with the traditional method, the method has the advantages that raw materials are easily available, the method is low in cost and is environmental friendly, reaction conditions are mild, solvents are clean and environmental friendly, equipment can be protected against corrosion under the neutral conditions, the catalyst is high in acid resistance, and the method is applicable to industrial production.
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Paragraph 0035; 0036
(2016/10/31)
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- Kinetic and Mechanistic Examination of Acid-Base Bifunctional Aminosilica Catalysts in Aldol and Nitroaldol Condensations
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The kinetic and mechanistic understanding of cooperatively catalyzed aldol and nitroaldol condensations is probed using a series of mesoporous silicas functionalized with aminosilanes to provide bifunctional acid-base character. Mechanistically, a Hammett analysis is performed to determine the effects of electron-donating and electron-withdrawing groups of para-substituted benzaldehyde derivatives on the catalytic activity of each condensation reaction. This information is also used to discuss the validity of previously proposed catalytic mechanisms and to propose a revised mechanism with plausible reaction intermediates. For both reactions, electron-withdrawing groups increase the observed rates of reaction, though resonance effects play an important, yet subtle, role in the nitroaldol condensation, in which a p-methoxy electron-donating group is also able to stabilize the proposed carbocation intermediate. Additionally, activation energies and pre-exponential factors are calculated via the Arrhenius analysis of two catalysts with similar amine loadings: one catalyst had silanols available for cooperative interactions (acid-base catalysis), while the other was treated with a silanol-capping reagent to prevent such cooperativity (base-only catalysis). The values obtained for activation energies and pre-exponential factors in each reaction are discussed in the context of the proposed mechanisms and the importance of cooperative interactions in each reaction. The catalytic activity decreases for all reactions when the silanols are capped with trimethylsilyl groups, and higher temperatures are required to make accurate rate measurements, emphasizing the vital role the weakly acidic silanols play in the catalytic cycles. The results indicate that loss of acid sites is more detrimental to the catalytic activity of the aldol condensation than the nitroaldol condensation, as evidenced by the significant decrease in the pre-exponential factor for the aldol condensation when silanols are unavailable for cooperative interactions. Cooperative catalysis is evidenced by significant changes in the pre-exponential factor, rather than the activation energy for the aldol condensation.
- Collier, Virginia E.,Ellebracht, Nathan C.,Lindy, George I.,Moschetta, Eric G.,Jones, Christopher W.
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p. 460 - 468
(2016/01/12)
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- Discovery of New Monocarbonyl Ligustrazine-Curcumin Hybrids for Intervention of Drug-Sensitive and Drug-Resistant Lung Cancer
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The elevation of oxidative stress preferentially in cancer cells by inhibiting thioredoxin reductase (TrxR) and/or enhancing reactive oxygen species (ROS) production has emerged as an effective strategy for selectively targeting cancer cells. In this study, we designed and synthesized 21 ligustrazine-curcumin hybrids (10a-u). Biological evaluation indicated that the most active compound 10d significantly inhibited the proliferation of drug-sensitive (A549, SPC-A-1, LTEP-G-2) and drug-resistant (A549/DDP) lung cancer cells but had little effect on nontumor lung epithelial-like cells (HBE). Furthermore, 10d suppressed the TrxR/Trx system and promoted intracellular ROS accumulation and cancer cell apoptosis. Additionally, 10d inhibited the NF-κB, AKT, and ERK signaling, P-gp-mediated efflux of rhodamine 123, P-gp ATPase activity, and P-gp expression in A549/DDP cells. Finally, 10d repressed the growth of implanted human drug-resistant lung cancer in mice. Together, 10d acts a novel TrxR inhibitor and may be a promising candidate for intervention of lung cancer.
- Ai, Yong,Zhu, Bin,Ren, Caiping,Kang, Fenghua,Li, Jinlong,Huang, Zhangjian,Lai, Yisheng,Peng, Sixun,Ding, Ke,Tian, Jide,Zhang, Yihua
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p. 1747 - 1760
(2016/03/25)
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- Iron(III) phthalocyanine chloride-catalyzed oxidation-aromatization of α,β-unsaturated ketones with hydrazine hydrate: Synthesis of 3,5-disubstituted 1H-pyrazoles
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We have developed an iron(III) phthalocyanine chloride-catalyzed oxidation-aromatization of α,β-unsaturated ketones with hydrazine hydrate. Various 3,5-disubstituted 1H-pyrazoles were obtained in good to excellent yields. This method offers several advantages, including room-temperature conditions, short reaction time, high yields, simple work-up procedure, and use of air as an oxidant. The catalyst can be recovered and reused five times without loss of activity.
- Zhao, Junlong,Qiu, Jun,Gou, Xiaofeng,Hua, Chengwen,Chen, Bang
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p. 571 - 578
(2016/04/20)
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- Synthesis and neuroprotective evaluation of (E)-3,4-dihydroxystyryl p-substituted-phenethyl ketone derivatives against inflammatory and oxidative injury
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(E)-3,4-dihydroxystyryl p-substituted-phenethyl ketones and their 3,4-diacetylated derivatives were synthesized and examined their neuroprotective activities to further study the effect of p-substituents on the aromatic ring. The results revealed that steric hindrance effect of p-substituents has impact on neuroprotective activities against inflammatory and oxidative injury. Introduction of the bulkier groups are more beneficial to improve the neuroprotective activities than smaller groups. Compounds (4–5h, 4–5i and 4–5e) with p-substituted trifluoromethyl, isopropyl and t-butyl groups exhibited the best effects among all the target compounds.
- Cheng, Can,Ning, Xianling,Luo, Yongming,Tian, Chao,Wang, Xiaowei,Guo, Ying,Liu, Junyi,Zhang, Zhili
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p. 1678 - 1685
(2016/07/30)
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- NMR and DFT Insight into the Synergistic Role of Bovine Serum Albumin–Ionic Liquid for Multicomponent Cascade Aldol/Knoevenagel–thia-Michael/Michael Reactions in One Pot
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The synergistic combination of two catalysts is an emerging strategy towards the formation of unprecedented complex molecules, and herein bovine serum albumin (BSA) and the neutral ionic liquid 1-butyl-3-methylimidazolium bromide ([bmim]Br) are used together for the first time towards multiple C?C and C?S bond-formation reactions in one pot under metal-free, acid-free, and base-free conditions by merging two classical named reactions, that is, aldol condensation (AC) and thia-Michael addition (TMA) for the cascade chemoselective generation of β-aryl-β-sulfido carbonyl compounds from aliphatic ketones, aromatic aldehydes, and thiols. NMR spectroscopy and DFT calculations studies provided insight into the synergism, progress, and mechanism of the reaction, and control experiments highlighted that the single catalysts (BSA or IL) alone did not allow even the first AC step to proceed. Moreover this synergistic BSA–[bmim]Br catalytic system offers the step-economical synthesis of the anticoagulant warfarin through sequential aldol–Michael addition reactions and potent pyridine analogues through a Knoevenagel–Michael route. Besides, the recyclability of the catalytic system (up to 5 times) with the generation of water as a byproduct makes our one-pot protocol more economically efficient and synthetically attractive than traditional methods.
- Thopate, Yogesh,Singh, Richa,Sinha, Arun K.,Kumar, Vikash,Siddiqi, Mohammad Imran
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p. 3050 - 3056
(2016/10/11)
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- A multicomponent pathway-inspired regioselective synthesis of 2,3,4-trisubstituted 1H-pyrroles via [3+2] cycloaddition reaction
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A copper catalyzed regioselective synthesis of 2,3,4-trisubstituted 1H-pyrroles using a novel three-component coupled domino reaction of aldehydes, ketones and alkyl isocyanoacetates is reported. This transformation proceeds through the formation of a chalcone followed by a [3+2] cycloaddition reaction to obtain α-cuprioisocyanide, a cyclic organocopper intermediate, which on copper-hydrogen exchange followed by oxidation exclusively offers 2,3,4-trisubstituted 1H-pyrrole.
- Kalmode, Hanuman P.,Vadagaonkar, Kamlesh S.,Murugan, Kaliyappan,Chaskar, Atul C.
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p. 4631 - 4639
(2015/06/16)
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- Synthesis of α-Tertiary Amine Derivatives by Intermolecular Hydroamination of Unfunctionalized Alkenes with Sulfamates under Trifluoromethanesulfonic Acid Catalysis
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An efficient and mild trifluoromethanesulfonic acid-catalyzed hydroamination of unfunctionalized alkenes to afford α-tertiary amine derivatives at temperatures as low as room temperature is reported. 2,2,2-Trifluoroethyl sulfamate was found to be the optimal nitrogen source because its good solubility in both organic solvents and water facilitated both conversion and purification. The reaction conditions were compatible with a variety of substrate functional groups and afforded moderate to good yields. The desired amine compounds could be obtained easily by means of a mild, one-pot, redox-neutral deprotection procedure. Caryolane amine was synthesized with excellent chemo- and regioselectivities by means of a cascade hydroamination reaction of β-caryophyllene.
- Fei, Jun,Wang, Zhen,Cai, Zheren,Sun, Hao,Cheng, Xu
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supporting information
p. 4063 - 4068
(2016/01/25)
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- Palladium nanoparticles supported on copper oxide as an efficient and recyclable catalyst for carbon(sp2)-carbon(sp2) cross-coupling reaction
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A convenient, mild and cost-effective synthesis of Pd/CuO nanoparticles by arc discharge of Cu in deionized (DI) water and electroless deposition of palladium was reported. The obtained nanoparticles were thoroughly characterized by using techniques like TEM, XRD, FE-SEM and EDS. The synthesized nanoparticles demonstrated excellent catalytic activity in Heck coupling reaction under aerobic conditions. The effects of catalyst composition, solvent and bases, aryl halides or olefins species on corresponding products were systematically investigated. High product yields, elimination of ligand and homogeneous catalysts, broad substrate scope and easy work up are important features of this method. In addition, the catalyst could be reused for five more consecutive recycles.
- Nasrollahzadeh, Mahmoud,Sajadi, S. Mohammad,Rostami-Vartooni, Akbar,Azarian, Abbas
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p. 150 - 154
(2015/04/14)
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- Palladium nanoparticles stabilised by PTA derivatives in glycerol: Synthesis and catalysis in a green wet phase
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Palladium nanoparticles stabilised by N-substituted 1,3,5-triaza-7-phosphaadamantane ionic ligands were synthesised from Pd(II) precursors and characterised in neat glycerol, observing an important effect of the phosphine nature in the dispersion of the nanoclusters in solution. The most homogeneously dispersed nanoparticles (Pd1a) led to the best catalytic behaviour in the benchmark Suzuki-Miyaura reaction. From this screening, Pd1a was applied in different CC cross-couplings and hydrogenation reactions, isolating the expected products in high yields (> 90%). An efficient catalyst immobilisation in glycerol was attained (up to ten runs without any sign of activity loss).
- Chahdoura, Faouzi,Favier, Isabelle,Pradel, Christian,Mallet-Ladeira, Sonia,Gómez, Montserrat
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- Synthesis of Polysubstituted Pyridines via a One-Pot Metal-Free Strategy
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An efficient strategy for the one-pot synthesis of polysubstituted pyridines via a cascade reaction from aldehydes, phosphorus ylides, and propargyl azide is reported. The reaction sequence involves a Wittig reaction, a Staudinger reaction, an aza-Wittig reaction, a 6π-3-azatriene electrocyclization, and a 1,3-H shift. This protocol provides quick access to the polysubstituted pyridines from readily available substrates in good to excellent yields.
- Wei, Hongbo,Li, Yun,Xiao, Ke,Cheng, Bin,Wang, Huifei,Hu, Lin,Zhai, Hongbin
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supporting information
p. 5974 - 5977
(2016/01/09)
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- Graphene based material as a base catalyst for solvent free Aldol condensation and Knoevenagel reaction at room temperature
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Graphene oxide (GO) acts as a highly active heterogeneous base catalyst for a wide variety of reactions. Here we have described the catalytic activities of GO in the condensation reaction of various substituted benzaldehydes with acetophenone (aldol condensation) and with active methylene compound malononitrile (Knoevenagel reaction) at room temperature under solvent free condition. GO is characterized by powder X-ray diffraction (XRD), UV-visible spectra, Fourier transform infrared spectroscopy (FT-IR) and AFM. The experimental results showed that the GO had higher catalytic activity and it can be recycled without significant loss of its activity.
- Islam, Sk Manirul,Roy, Anupam Singha,Dey, Ram Chandra,Paul, Sumantra
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- Carbon quantum dots with photoenhanced hydrogen-bond catalytic activity in aldol condensations
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Carbon quantum dots (CQDs) were synthesized by an electrochemical etching method. The CQDs are well-dispersed with uniform size about 5 nm. FT-IR spectra suggest the presence of many hydroxyl groups on the surface of CQDs. Here, CQDs with diameter approximately 5 nm, directly used as effective heterogeneous nanocatalysts for H-bond catalysis in aldol condensations, show excellent photoenhanced catalytic ability (89% yields when 4-cyanobenzaldehyde is used). It demonstrated that aldol condensation between acetone and aromatic aldehydes resulted in higher yields with visible light irradiation than in the dark, confirming visible light is necessary for good conversion. The H-bond catalytic activities of CQDs can be significantly enhanced with visible light irradiation. The high catalytic activities of CQDs are due to highly efficient electron-accepting capabilities. Repeated catalytic experiments suggest that the CQD catalyst can be easily recycled as a heterogeneous catalyst with a long catalyst life.
- Han, Yuzhi,Huang, Hui,Zhang, Hengchao,Liu, Yang,Han, Xiao,Liu, Ruihua,Li, Haitao,Kang, Zhenhui
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p. 781 - 787
(2014/04/03)
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- Catalytic microwave-promoted direct aldol condensation using resin-bound secondary amine
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A series of polystyrene-supported imino group-bearing catalysts were prepared. A highly efficient combination of recyclable catalysts and microwave irradiation was developed as a green protocol for the direct aldol reaction. Notably, microwaves greatly shorten the reaction times to only 20 min and improve the yield significantly. Catalyst loading was reduced as well. Different aromatic aldehydes as aldol donors were subjected to our catalyst system and afforded the corresponding products in satisfactory yields. Additionally, the polymer-supported catalysts could be recovered by simple filtration and were reusable for at least four times without significant loss of reactivity. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]
- Liao, Fu Xu,Wang, Yu Guang,Zhu, Qing
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supporting information
p. 161 - 169
(2013/12/04)
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- Reduced graphene oxide supported piperazine in aminocatalysis
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Reduced graphene oxide (rGO) has been used as a support for piperazine to provide a heterogeneous bifunctional organocatalyst (rGO-NH) that is able to efficiently promote vintage organic transformations such as Knoevenagel, Michael and aldol reactions. The obtained results suggest a significant role of the support in the course of these reactions. This journal is the Partner Organisations 2014.
- Rodrigo, Eduardo,García Alcubilla, Beatriz,Sainz, Raquel,Fierro, J. L. García,Ferritto, Rafael,Cid, M. Belén
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supporting information
p. 6270 - 6273
(2014/06/09)
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- Wacker-type oxidation and dehydrogenation of terminal olefins using molecular oxygen as the sole oxidant without adding ligand
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An efficient and economical palladium-catalyzed oxidation system has been identified. The oxidation system, characterized by not adding ligand and using molecular oxygen as the sole oxidant, can realize the Tsuji-Wacker oxidation of terminal olefins and especially styrenes to methyl ketones; in addition, this system can achieve tandem Wacker oxidation-dehydrogenation of terminal olefins to α,β-unsaturated ketones.
- Wang, Yu-Fei,Gao, Ya-Ru,Mao, Shuai,Zhang, Yan-Lei,Guo, Dong-Dong,Yan, Zhao-Lei,Guo, Shi-Huan,Wang, Yong-Qiang
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supporting information
p. 1610 - 1613
(2014/04/17)
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- FLAVONE DERIVATIVES AND THEIR PREPARATIVE METHOD AND MEDICAL USE
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Flavone derivatives, preparative method of the derivatives and use thereof as medicaments for treating diabetes. The structure of the derivatives is presented by formula 1: In the structure, R1 and R2, which are identical or not, represent hydrogen atom, halogen, cyano, hydroxyl, trifluoromethyl, thio-methyl, benzyloxy, C1-C8 linear chain or branch chain alkyl, C1-C8 linear chain or branch chain alkoxy. The pharmacological test indicates that the flavone derivatives can significantly increase the glucose consumption of Hep-G2 cell with insulin resistance activity, promote translocation of glucose transporter 4 of skeletal muscle cells (L6GLUT4myc) at different level, and significantly increase glucose intake and utilization by cells. The test proves the fact for the first time that the flavone derivatives can significantly promote translocation of glucose transporter 4 of skeletal muscle cells, and one of the mechanisms for treating diabetes is activating the cell AMPK phosphorylation and phosphorylating the downstream ACC.
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Paragraph 0028
(2013/09/12)
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