- Regioselectivity of Friedlaender quinoline syntheses
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Optically active, bicyclic ketones were submitted to Friedlaender quinoline syntheses with 2-aminobenzaldehyde to yield regioisomeric linear or angular products. When starting from trans-configured ketones, the linear products are the major isomers (ratio
- Diedrich, Claas Lueder,Haase, Detlev,Saak, Wolfgang,Christoffers, Jens
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- Synthesis of an unusual quinazoline alkaloid: Theoretical and experimental investigations of its structural, electronic, molecular and biological properties
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An unusual quinazoline alkaloid (1) was obtained when 2-aminobenzaldehyde was refluxed with pyrrolidine in ethanol for 12 h. The synthesized compound was characterized using spectral data analysis augmented with X-ray and literature precedent. Single crys
- Lone, Shabir H.,Jameel, Salman,Bhat, Muzzaffar A.,Lone, Rayees A.,Butcher, Ray J.,Bhat, Khursheed A.
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- Tailored routes for home-made Bi-doped ZnO nanoparticles. Photocatalytic performances towards o-toluidine, a toxic water pollutant
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Herein we report the photodegradation of highly toxic o-toluidine in aqueous media (under UV irradiation), by using home-made bare and bismuth-doped ZnO nanoparticles. The latter powder was prepared by both a traditional impregnation method and by an innovative sol-gel synthesis, obtained using bismuth nitrate as precursor. Moreover, synthetic conditions (such as zinc salts and medium acidity) were varied in order to obtain different semiconductor nanopowders with diverse physico-chemical properties and, hence, photocatalytic performances. Both the disappearance and the mineralization of the pollutant molecule were followed by Linear Sweep Voltammetry and Total Organic Carbon techniques, respectively. Photocatalysis by-products were then identified by HPLC–MS (on eluates, after 3 h and 6 h) and ATR-FTIR (on used nanopowders) analyses. Thus, a new photodegradation pathway (with azo dimer derivatives in the first step) has been proposed. Bi-impregnated samples show high degree of mineralization, reducing the stability of the intermediates.
- Mostoni,Pifferi,Falciola,Meroni,Pargoletti,Davoli,Cappelletti
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- Visible-Light-Induced Morphological Changes of Giant Vesicles by Photoisomerization of a Ruthenium Aqua Complex
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Visible- and red-light responsive vesicles were prepared by incorporating a ruthenium aqua complex having two alkyl chains on tridentate and asymmetrical bidentate ligands (proximal-2: [Ru(C10tpy)(C10pyqu)OH2]2+, C10tpy=4′-decyloxy-2,2′;6′,2"-terpyridine, C10pyqu=2-[2′-(6′-decyloxy)-pyridyl]quinoline). The ruthenium complex of proximal-2 with closed alkyl chain geometry and a cylinder-like molecular shape exhibited photoisomerization to distal-2 with an open alkyl chain geometry and a cone-like shape, both in an aqueous solution and in vesicle dispersions. We observed that light irradiation of giant vesicles containing proximal-2 induced diverse morphological changes.
- Hirahara, Masanari,Tsukamoto, Akira,Goto, Hiroki,Tada, Shigeru,Yagi, Masayuki,Umemura, Yasushi
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- Non-covalent aggregation of discrete metallo-supramolecular helicates into higher assemblies by aromatic pathways: Structural and chemical studies of new aniline-based neutral metal(II) dihelicates
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Neutral manganese(II), iron(II), cobalt(II), nickel(II), zinc(II) and cadmium(II) complexes with an N-tosyl-substituted N4-donor Schiff base containing a 4,4′-methylenedianiline residue as spacer [H 2La: N,N′-bis(2-tosylaminobenzylidene)-4,4′- methylenedianiline], and the zinc(II) complex with an analogous ligand [H 2Lb: N,N′-bis(2-tosylaminobenzylidene)-4,4′- oxodianiline] have been prepared by an electrochemical procedure. FAB and ESI mass spectra of the complexes show peaks due to species corresponding to a general formula [M2(La,b)2 + H]+, thereby suggesting their dinuclear nature. A detailed study of the crystal packing in the unit cell of the zinc(II) complex with H2La shows that the helicates aggregate to form discrete prismatic moieties containing three molecules held together by π-π and σ-π interactions. Moreover, the ZnII neutral dihelicate with H 2Lb forms a 3D network in the solid state due to intermolecular π-stacking interactions. 1H NMR studies of the diamagnetic compounds reported herein have been performed. Finally, the ligand H2La and its ZnII and CdII complexes have been studied by spectrophotometric and spectrofluorimetric techniques in order to get a better understanding of the formation mechanisms of the complexes and of the nature of their fluorescence emission. Emission studies show that the ZnII and CdII dihelicates with H2L a display a green fluorescence in acetonitrile solution (λ = 473 nm, Φ = 0.03 and λ = 476 nm, Φ = 0.01, respectively). Wiley-VCH Verlag GmbH & Co. KGaA 2005.
- Vazquez, Miguel,Bermejo, Manuel R.,Licchelli, Maurizio,Gonzalez-Noya, Ana M.,Pedrido, Rosa M.,Sangregorio, Claudio,Sorace, Lorenzo,Garcia-Deibe, Ana M.,Sanmartin
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- Total synthesis of the cytotoxic alkaloid luotonin A
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The structure of luotonin A was unambiguously confirmed by total synthesis. Deprotonation of 3-oxo-1H-pyrrolo[3,4-b]quinoline gave an anion which was coupled with 2-sulfinylaminobenzoyl chloride (prepared by reaction of anthranilic acid with thionyl chlor
- Wang, Haishan,Ganesan
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- Synthesis, characterization, and application of a manganese Schiff base complex containing salicylaldehyde-poly(vinylamine)/SBA-15 as a novel heterogeneous hybrid catalyst
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A manganese Schiff base complex containing salicylaldehyde-poly(vinylamine) /SBA-15 (Mn-SA-PVAm/SBA-15) composite was prepared as a novel heterogeneous catalyst through in situ polymerization of vinylamine within the nano-channels of mesoporous silica SBA-15 without using any organo silica precursors. The catalyst was characterized well by elemental analysis, FT-IR, AAS, DRS UV-Vis, XRD, BET, SEM and TGA techniques. The catalytic activity of the supported metal complex was studied in the selective oxidation of benzyl alcohols using t-butyl hydroperoxide as an oxidant. The effects of reaction temperature, solvent and the amount of catalyst as well as the recyclability of the catalyst were investigated. The Royal Society of Chemistry 2013.
- Massah, Ahmad Reza,Kalbasi, Roozbeh Javad,Kaviyani, Somayeh
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- Copper-catalyzed Reaction of Anthranils with Methyl Ketones: Site-Selective C5-Dicarbonylation of Anthranils
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A copper-catalyzed site-selective C5-dicarbonylation reaction of anthranils has been developed for synthesis of 1,2-dicarbonyl compounds using methyl ketone as a commercially available carbonylation reagent. This process represents the first example to implement the C5-dicarbonylation of anthranils, which involves an oxidative Csp3-H/Csp2-H cross-coupling reaction along with thermolytic N?O bond cleavage. (Figure presented.).
- Zhuang, Shi-Yi,Tang, Yong-Xing,He, Cai,Chen, Xiang-Long,Xue, Wei-Jian,Wu, Yan-Dong,Wu, An-Xin
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- Fe3O(OAc)6(Py)3 Mediated Reduction of Aromatic Nitro Compounds with 2-Mercaptoethanol
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Aromatic nitro compounds were selectively reduced by 2-mercaptoethanol in the presence of Fe3O(OAc)6(Py)3 to give the corresponding amines in good yields.
- Murata, Satoru,Miura, Masahiro,Nomura, Masakatsu
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- Discovery of seneciobipyrrolidine derivatives for the amelioration of glucose homeostasis disorders through 4E-BP1/Akt/AMPK signaling activation
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Modulating the glucose transport in skeletal muscle is a promising strategy for ameliorating glucose homeostasis disorders. However, the complicated mechanisms of glucose transport make it difficult to find compounds therapeutically relevant molecular mechanisms of action, while phenotypic screening is thought to be an alternative approach to mimic the cell state of interest. Here, we report (±)-seneciobipyrrolidine (1a) is first found to enhance glucose uptake in L6 myotubes through phenotype-based screening. Further SAR investigation led to the identfication of compound A27 (EC50 = 2.7 μM). Proteomiic analysis discloses the unique function mechanism of A27 through upregulating the level of the eukaryotic translation initiation factor 4E-binding protein 1 (4E-BP1), subsequently enhancing the Akt and AMPK phosphorylation, thereby promoting the glucose uptake. Chronic oral administration of A27 significantly lowers blood glucose and improves glucose tolerance in db/db mice. This work is new research on seneciobipyrrolidine derivatives, providing a promising avenue for ameliorating glucose homeostasis.
- Che, Jinxin,Ma, Canliang,Lu, Jialiang,Chen, Binhui,Shi, Qiuqiu,Jin, Xinxin,Song, Rui,Xu, Fan,Gan, Lishe,Li, Jingya,Hu, Yongzhou,Dong, Xiaowu
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- Augmenting Adaptive Machine Learning with Kinetic Modeling for Reaction Optimization
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We combine random sampling and active machine learning (ML) to optimize the synthesis of isomacroin, executing only 3% of all possible Friedl?nder reactions. Employing kinetic modeling, we augment machine intuition by extracting mechanistic knowledge and
- Almeida, A. Filipa,Ataíde, Filipe A. P.,Loureiro, Rui M. S.,Moreira, Rui,Rodrigues, Tiago
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p. 14192 - 14198
(2021/07/28)
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- NaI/PPh3-Mediated Photochemical Reduction and Amination of Nitroarenes
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A mild transition-metal- and photosensitizer-free photoredox system based on the combination of NaI and PPh3 was found to enable highly selective reduction of nitroarenes. This protocol tolerates a broad range of reducible functional groups such as halogen (Cl, Br, and even I), aldehyde, ketone, carboxyl, and cyano. Moreover, the photoredox catalysis with NaI and stoichiometric PPh3 provides also an alternative entry to Cadogan-type reductive amination when o-nitrobiarenes were used.
- Qu, Zhonghua,Chen, Xing,Zhong, Shuai,Deng, Guo-Jun,Huang, Huawen
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supporting information
p. 5349 - 5353
(2021/07/21)
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- Exploiting novel rotors with auxochromic dynamic motors for monitoring lysosomal viscosity
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Organelles like lysosomes usually exhibit dynamic changes of locations, morphologies, and components, which could be reflected by the local viscosity. For monitoring lysosomal viscosity, a novel rotor P7-B was introduced with an improved auxochromic dynam
- Xu, Jian-Fei,Gu, Jin,Qi, Ya-Lin,Zhang, Meng,Chen, Jian,Li, Dong-Dong,Yang, Yu-Shun,Lv, Peng-Cheng,Zhu, Hai-Liang
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- A highly effective green catalyst Ni/Cu bimetallic nanoparticles supported by dendritic ligand for chemoselective oxidation and reduction reaction
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The highly active Ni/Cu bimetallic nanoparticles (NPs) of the different molar ratios of Ni and Cu (1:1, 1:3, 3:1) assisted by dendritic ligand 2,4,6-Tris (di-4-chlorobenzamido)-1,3-diazine were synthesized successfully confirmed by Scanning Electron Microscopy (SEM), Electron Diffraction X-ray (EDX), X-ray fluorescence spectroscopy (XRF), X-ray diffraction (XRD), and Transmission Electron Microscopy (TEM) analysis. These NPs were studied as a heterogeneous catalyst for the chemoselective oxidation of alcohol to the corresponding aldehyde at 30?min and chemoselective reduction of aromatic nitro substituents to the corresponding amino substituents at 20?min, while the Ni/Cu (3:1) NPs were found to be the most effective among other Ni/Cu?(1:1)?and Ni/Cu?(1:3)?NPs at room temperature under mild conditions. The Ni/Cu (3:1) NPs can be recycled for at least five successive runs with no perceptible decrease in catalytic activity. Graphic abstract: [Figure not available: see fulltext.]
- Islam, Md. Sayedul,Khan, Md. Wahab
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p. 2353 - 2369
(2021/01/07)
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- Silver-Catalyzed Three-Component Coupling Reaction of Amines, 2-Isocyanobenzaldehydes, and 2,2,2-Trifluorodiazoethane and Synthesis of Trifluoromethyl-Substituted Indolo[1,2-c]quinazolines
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A silver-catalyzed three-component coupling reaction of amines, 2-isocyanobenzaldehydes, and 2,2,2-trifluorodiazoethane has been developed. This reaction provides an efficient method for the construction of CF3-containing dihydroquinazolines. On the basis of this reaction, using trifluorodiazoethyl-substituted dihydroquinazolines as synthons, trifluoromethyl-substituted indolo[1,2-c]quinazolines were prepared in high yields via a TBHP/KI-mediated sequential intramolecular cyclization and aromatization process. (Figure presented.).
- Meng, Xiang-He,Peng, Ju-Yin,Yang, Ming,Zhao, Yu-Long
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supporting information
p. 244 - 250
(2020/12/01)
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- PPTS-Catalyzed Bicyclization Reaction of 2-Isocyanobenzaldehydes with Various Amines: Synthesis of Diverse Fused Quinazolines
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A PPTS (pyridinium p-toluenesulfonate)-catalyzed bicyclization reaction of 2-isocyanobenzaldehydes as 1,5-dielectrophiles with various amines has been developed. The reaction not only provides a simple and efficient strategy for the assembly of structurally diverse fused quinazoline derivatives from readily available substrates under metal-free and mild conditions in a single step with only water and hydrogen as the by-products, but also opens the way to the application of o-formyl arylisocyanides in the synthesis of nitrogen-containing heterocycles. (Figure presented.).
- Meng, Xiang-He,Wu, Dan-Ni,Zhang, Yu-Jia,Zhao, Yu-Long
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supporting information
p. 1923 - 1929
(2021/02/26)
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- Activated Mont K10-Carbon supported Fe2O3: A versatile catalyst for hydration of nitriles to amides and reduction of nitro compounds to amines in aqueous media
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The iron oxide was successfully supported on activated clay/carbon through an experimentally viable protocol for both hydrations of nitrile to amide and reduction of nitro compounds to amines. The as-prepared catalyst has been extensively characterised by XPS, SEM-EDX, TEM, TGA, BET surface area measurements and powdered X-ray diffraction (PXRD). A wide variety of substrates could be converted to the desired products with good to excellent yields by using water as a green solvent for both the reactions. The catalyst was recyclable and reusable up to six consecutive cycles without compromising its catalytic proficiency. Graphical abstract: Activated Mont K10 carbon-supported Fe2O3 is a very efficient and versatile heterogeneous catalytic system for hydration of nitriles to amides and reduction of nitro compounds to amines and can be reused up to six consecutive cycles without significant loss in catalytic activity.[Figure not available: see fulltext.].
- Rahman, Taskia,Borah, Geetika,Gogoi, Pradip K
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- Synthesis of CoFe2O4@Pd/Activated carbon nanocomposite as a recoverable catalyst for the reduction of nitroarenes in water
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Efficient reduction of nitro compounds into amines is an important industrial transformation. So, it is a great deal to design new catalysts for efficient reduction of the nitro compounds especially in water. In this work, a new magnetic Pd/activated carbon nanocomposite (CoFe2O4@Pd/AC) was synthesized via metal-impregnation-pyrolysis method. The CoFe2O4@Pd/AC was fully characterized by FT-IR, PXRD, FESEM, TEM, VSM, EDX-mapping and BET techniques. The results showed that CoFe2O4@Pd/AC is a highly reactive and easily recoverable magnetic catalyst for the reduction of the nitro compounds by using NaBH4 in water. For instance, aniline was obtained in high yield (99%) after 75 ?min at 25 ?C by using just 6 ?mg of the catalyst. In addition, CoFe2O4@Pd/AC was recovered by a simple magnetic decantation and it exhibits stable activity and remains intact during the catalytic process with no significant loss in activity (8 cycles).
- Hamadi, Hosein,Kazeminezhad, Iraj,Mohammadian, Sara
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- Silver nanoparticles supported on P, Se-codoped g-C3N4 nanosheet as a novel heterogeneous catalyst for reduction of nitroaromatics to their corresponding amines
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P, Se-codoped g-C3N4 (PSeCN) nanosheet was in situ prepared by facile thermal polymerization of melamine, phosphonitrilic chloride trimer, and selenium black powder as the precursors. It was found as a suitable support for the immobilization of silver nanoparticles (Ag NPs). The prepared nanocatalyst was fully characterized via standard analysis methods including EDX, ICP-OES, XRD, FT-IR, SEM, TEM, and BET. This PSeCN/Ag nanocatalyst with a higher specific surface area compared with CN, showed excellent catalytic activity towards the reduction of several nitroaromatic compounds using sodium borohydride (NaBH4) in short reaction times with high efficiency and good selectivity in water as a green solvent. Significantly, the above-mentioned nanocomposite could be reused six times without appreciable loss of its catalytic activity.
- Elhampour, Ali,Heravi, Majid M.,Nemati, Firouzeh,Piri, Mohadese
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- Metal-Free Annulation of 2-Nitrobenzyl Alcohols and Tetrahydroisoquinolines toward the Divergent Synthesis of Quinazolinones and Quinazolinethiones
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A simple metal-free method for the synthesis of quinazolinones from commercially available 2-nitrobenzyl alcohols and tetrahydroisoquinolines is developed. The reaction conditions were tolerant of an array of functionalities such as halogen, tertiary amine, protected alcohol, and ester groups. Under nearly identical conditions, quinazolinethiones were obtained in the presence of elemental sulfur and suitable mediators.
- Le, Nhan T. H.,Ly, Duc,Nguyen, Khang X.,Nguyen, Thao T.,Nguyen, Tung T.,Nguyen, Vy P. T.,Pham, Phuc H.,Phan, Nam T. S.,Tran, Cam T. H.
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supporting information
(2022/01/03)
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- Iron(III) Nitrate/TEMPO-Catalyzed Aerobic Alcohol Oxidation: Distinguishing between Serial versus Integrated Redox Cooperativity
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Aerobic alcohol oxidations catalyzed by transition metal salts and aminoxyls are prominent examples of cooperative catalysis. Cu/aminoxyl catalysts have been studied previously and feature "integrated cooperativity", in which CuII and the aminoxyl participate together to mediate alcohol oxidation. Here we investigate a complementary Fe/aminoxyl catalyst system and provide evidence for "serial cooperativity", involving a redox cascade wherein the alcohol is oxidized by an in situ-generated oxoammonium species, which is directly detected in the catalytic reaction mixture by cyclic step chronoamperometry. The mechanistic difference between the Cu- and Fe-based catalysts arises from the use iron(III) nitrate, which initiates a NOx-based redox cycle for oxidation of aminoxyl/hydroxylamine to oxoammonium. The different mechanisms for the Cu- and Fe-based catalyst systems are manifested in different alcohol oxidation chemoselectivity and functional group compatibility.
- Mao, Kaining,Nutting, Jordan E.,Stahl, Shannon S.
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supporting information
p. 10565 - 10570
(2021/07/28)
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- Copper-catalyzed synthesis of pyrido-fused quinazolinones from 2-aminoarylmethanols and isoquinolines or tetrahydroisoquinolines
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Pyrido-fused quinazolinones were synthesizedviacopper-catalyzed cascade C(sp2)-H amination and annulation of 2-aminoarylmethanols with isoquinolines or pyridines. The transformation proceeded readily in the presence of a commercially available CuCl2catalyst with molecular oxygen as a green oxidant. Moreover, the dehydrogenative cross-coupling of 2-aminoarylmethanols with tetrahydroisoquinolines was explored, in which CuBr exhibited higher catalytic activity than CuCl2. Broad substrate scope with good tolerance of functionalities was observed under the optimized reaction conditions. The bioactive naturally occurring alkaloid rutaecarpine could be obtained by this strategy. The remarkable feature of this protocol is that complicated heterocyclic structures are readily achieved in a single synthetic step from easily accessible reactants and catalysts. This pathway to pyrido-fused quinazolinones would be complementary to existing protocols.
- Ly, Duc,Nguyen, Duyen K.,Nguyen, Khang X.,Nguyen, Khoa D.,Nguyen, Thao T.,Nguyen, Tung T.,Pham, Phuc H.,Phan, Nam T. S.
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supporting information
p. 4726 - 4732
(2021/06/09)
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- Mild and efficient copper-catalyzed oxidative cyclization of oximes with 2-aminobenzyl alcohols at room temperature: synthesis of polysubstituted quinolines
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A simple and efficient ligand-free Cu-catalyzed protocol for the synthesis of polysubstituted quinolinesviaoxidative cyclization of oxime acetates with 2-aminobenzyl alcohols at room temperature has been developed. The presented approach provides a new synthetic pathway leading to polysubstituted quinolines with good functional group tolerance under mild conditions. Moreover, this transformation can be applied for the preparation of quinolines on a gram scale. Oxime acetates serve as the internal oxidants in the reactions, thus making this method very attractive.
- Liu, Yan-Yun,Wei, Yang,Huang, Zhi-Hui,Liu, Yilin
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supporting information
p. 659 - 666
(2021/02/06)
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- BTP-Rh@g-C3N4 as an efficient recyclable catalyst for dehydrogenation and borrowing hydrogen reactions
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Highly active catalysts play an important role in modern catalysis. A novel and efficient ligand benzotriazole-pyrimidine (BTP) and the corresponding rhodium composite on C3N4 were successfully synthesized. The resulting rhodium composite was fully characterized by scanning electron microscopy (SEM), transmission electron microscopy (TEM), x-ray diffraction (XRD), thermogravimetric analysis (TGA), and x-ray photoelectron spectroscopy (XPS). The obtained composite exhibited good catalytic activity and good recovery performance in the synthesis of quinoxaline from 2-aminobenzyl alcohol and benzonitrile, and more than 20 quinoxalines were obtained in good yields. Additionally, it also showed that rhodium composite could achieved good catalytic performance in the synthesis of functionalized ketone through borrowing hydrogen strategy.
- Hu, Wenkang,Liu, Hongqiang,Luo, Lan,Wang, Dawei,Zeng, Wei
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- Unexpected Annulation between 2-Aminobenzyl Alcohols and Benzaldehydes in the Presence of DMSO: Regioselective Synthesis of Substituted Quinolines
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An unexpected annulation among 2-aminobenzyl alcohols, benzaldehydes, and DMSO to quinolines has been disclosed. For the reported annulation between 2-aminobenzyl alcohols and benzaldehydes, the change of the solvent from toluene to DMSO led to the change of the product from the diheteroatomic cyclic benzoxazines to monoheteroatomic cyclic quinolines. This annulation can be used to synthesize regioselectively different substituted quinolines by the choice of different 2-amino alcohols, aldehydes, and sulfoxides as substrates. Interestingly, introducing substituent groups to the α-position of sulfoxides resulted in the interchange of the positions between benzaldehydes and sulfoxides in the product quinolines. On the basis of the control experiments and literatures, a plausible mechanism for this annulation was proposed.
- Yang, Tonglin,Nie, Zhi-Wen,Su, Miao-Dong,Li, Hui,Luo, Wei-Ping,Liu, Qiang,Guo, Can-Cheng
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p. 15228 - 15241
(2021/10/25)
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- Efficient synthesis of quinazolines by the iron-catalyzed acceptorless dehydrogenative coupling of (2-aminophenyl)methanols and benzamides
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The acceptorless dehydrogenation coupling (ADC) of (2-aminophenyl)methanols with benzamides was achieved with catalytic FeCl2·4H2O in an efficient synthesis of quinazolines. This simple catalytic system is atom-economical, environmentally benign and suited to a variety of substrates.
- Zhang, Shi-Qi,Cui, Yao,Guo, Bin,Young, David J.,Xu, Ze,Li, Hong-Xi
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- Designed pincer ligand supported Co(ii)-based catalysts for dehydrogenative activation of alcohols: Studies onN-alkylation of amines, α-alkylation of ketones and synthesis of quinolines
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Base-metal catalystsCo1,Co2andCo3were synthesized from designed pincer ligandsL1,L2andL3having NNN donor atoms respectively.Co1,Co2andCo3were characterized by IR, UV-Vis. and ESI-MS spectroscopic studies. Single crystal X-ray diffraction studies were investigated to authenticate the molecular structures ofCo1andCo3. CatalystsCo1,Co2andCo3were utilized to study the dehydrogenative activation of alcohols forN-alkylation of amines, α-alkylation of ketones and synthesis of quinolines. Under optimized reaction conditions, a broad range of substrates including alcohols, anilines and ketones were exploited. A series of control experiments forN-alkylation of amines, α-alkylation of ketones and synthesis of quinolines were examined to understand the reaction pathway. ESI-MS spectral studies were investigated to characterize cobalt-alkoxide and cobalt-hydride intermediates. Reduction of styrene by evolved hydrogen gas during the reaction was investigated to authenticate the dehydrogenative nature of the catalysts. Probable reaction pathways were proposed forN-alkylation of amines, α-alkylation of ketones and synthesis of quinolines on the basis of control experiments and detection of reaction intermediates.
- Singh, Anshu,Maji, Ankur,Joshi, Mayank,Choudhury, Angshuman R.,Ghosh, Kaushik
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supporting information
p. 8567 - 8587
(2021/06/30)
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- Cascade Reaction of α, β-Unsaturated Ketones and 2-Aminoaryl Alcohols for the Synthesis of 3-Acylquinolines by a Copper Nanocatalyst
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3-Acylquinolines possess widespread applications in functional chemicals. However, the convenient and selective synthesis of such important substructures has to date remained a challenge. Herein, we report a method to access 3-acylquinolines from α, β-unsaturated ketones and 2-aminoaryl alcohols in one pot with a copper nanocatalyst supported on nitrogen-silica-doped carbon (Cu/N?SiO2?C). Mechanistically, the construction of the product involves a cascade procedure including radical-type oxidation of 2-aminoaryl alcohols, aza-Michael addition and annulation. This developed protocol proceeds with merits of mild reaction conditions, good functional group tolerance, earth-abundant and reusable copper catalyst, easily available stocks and O2 as the sole oxidant, which provides an alternative way for the sustainable synthesis of quinoline derivatives. (Figure presented.).
- Liu, Yuan,Wang, Chen,Tong, Yixin,Ling, Yong,Zhou, Changjian,Xiong, Biao
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supporting information
p. 4422 - 4429
(2021/08/07)
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- Hierarchical CeO2@N-C Ultrathin Nanosheets for Efficient Selective Oxidation of Benzylic Alcohols in Water
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A monodisperse CeO2@N-C ultrathin nanosheet self-assembled hierarchical structure (USHR) has been prepared by metal-organic framework template methods. The uniform coating of nitrogen-doped carbon (N-C) layers could play an important role in the adsorption and activation of benzylic alcohol. The unique 3D hierarchical structure self-assembled by ultrathin nanosheets provided enough active sites for the catalytic reaction. Therefore, the CeO2@N-C USHR can afford excellent catalytic performance for selective oxidation of benzylic alcohols in water.
- Han, Xiguang,Hao, Juan,Long, Zhouyang,Sun, Liming,Wang, Xiaojun,Zhan, Wenwen
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supporting information
p. 7732 - 7737
(2021/06/27)
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- Palladium-catalyzed carbonylative cyclization of benzyl chlorides with anthranils for the synthesis of 3-arylquinolin-2(1: H)-ones
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An efficient carbonylative procedure for the synthesis of 3-arylquinoin-2(1H)-ones has been established. Through a palladium-catalyzed aminocarbonylation of benzyl chlorides with anthranils, a variety of 3-arylquinoin-2(1H)-one products were obtained in moderate to excellent yields with good functional group tolerance. This journal is
- Liu, Jian-Li,Xu, Ren-Rui,Wang, Wei,Qi, Xinxin,Wu, Xiao-Feng
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supporting information
p. 3584 - 3588
(2021/05/04)
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- Non-alkylator anti-glioblastoma agents induced cell cycle G2/M arrest and apoptosis: Design, in silico physicochemical and SAR studies of 2-aminoquinoline-3-carboxamides
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Malignant gliomas are the most common brain tumors, with generally dismal prognosis, early clinical deterioration and high mortality. Recently, 2-aminoquinoline scaffold derivatives have shown pronounced activity in central nervous system disorders. We herein reported a series of 2-aminoquinoline-3-carboxamides as novel non-alkylator anti-glioblastoma agents. The synthesized compounds showed comparable activity to cisplatin against glioblastoma cell line U87 MG in vitro. Among them, we found that 6a displayed good inhibitory activity against A172 and U118 MG glioblastoma cell lines and induced cell cycle arrest in the G2/M phase and apoptosis in U87 MG by flow cytometry analysis. Additionally, 6a displayed low cytotoxicity to several normal human cell lines. In silico study showed 6a had promising physicochemical properties and was predicted to cross the blood–brain barrier. Moreover, preliminary structure–activity relationships are also investigated, shedding light on further modifications towards more potent agents on this series of compounds. Our results suggest this compound has a promising potential as an anti-glioblastoma agent with a differential effect between tumor and non-malignant cells.
- Gu, Xiangyu,Liu, Jianwen,Ni, Xintong,Qi, Yingxue,Qian, Xuhong,Shao, Xusheng,Xu, Xiaoyong,Yuan, Pengtao
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- Ambient reductive synthesis of N-heterocyclic compounds over cellulose-derived carbon supported Pt nanocatalyst under H2atmosphere
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N-heterocyclic compounds are important chemicals, and their reductive synthesis using H2 under mild conditions is attractive but challenging. Herein, we report chemoselective hydrogenation of 2-nitroacylbenzenes to 2,1-benzisoxazoles under ambient conditions for the first time, wihch is achieved over cellulose-derived carbon (c-C) supported Pt nanocatalyst (Pt/c-C), and a series of 2,1-benzisoxazoles can be obtained in excellent yields. Pt/c-C also shows high performance for ambient reductive amination of levulinic acid with H2, accessing various pyrrolidones in excellent yields. The systematic studies indicated that the c-C support played multiple roles in catalysis with enhancing electron density of the Pt nanoparticles and activating reactant molecules. Especially, the O-containing groups on the c-C surface provided the c-C support with both acid and base features, thus endowing Pt/c-C with high performances. This work provides an accessible and highly efficient catalyst for reductive synthesis of N-heterocycles using H2 under ambient conditions, which may have promising applications.
- Wu, Yunyan,Wu, Yunyan,Zhao, Yanfei,Zhao, Yanfei,Wang, Huan,Wang, Huan,Zhang, Fengtao,Zhang, Fengtao,Li, Ruipeng,Li, Ruipeng,Xiang, Junfeng,Wang, Zhenpeng,Han, Buxing,Liu, Zhimin
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p. 3820 - 3826
(2020/07/06)
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- Cobalt oxide NPs immobilized on environmentally benign biological macromolecule-derived N-doped mesoporous carbon as an efficient catalyst for hydrogenation of nitroarenes
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Highly nitrogen-doped mesoporous carbon (N-mC) material incorporated cobalt oxide nanoparticles was synthesized through simple pyrolysis of environmentally friendly chitosan-polyaniline-Co(OAc)2 precursor in one-step. The as-prepared catalyst named CoO&at;N-mC with 14.65 ?wtpercent nitrogen content was characterized by different analysis techniques. The heterogeneous catalyst exhibits outstanding catalytic activity for the reduction of a variety of nitroaromatic compounds in the presence of NaBH4 as a reducing agent in water as a green solvent at 75 ?°C. Utilization of natural biological macromolecules such as chitosan as green and cheap starting material with harmless aniline and earth-abundant cobalt salt, facile synthesis, excellent product yield, short reaction time, high chemoselectivity, sustainable and mild reaction condition, and reusability of catalyst for at least five cycles without any significant decline in the catalytic efficiency are some prominent merits of this new nanocatalyst.
- Elhampour, Ali,Nanadegani, Zahra Soleimani,Nemati, Firouzeh,Rangraz, Yalda
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- OLIGOAZAFLUORENE MONOMER
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PROBLEM TO BE SOLVED: To provide an oligoazafluorene monomer that exhibits optical properties, heat resistance, thermal stability and good solubility. SOLUTION: The oligoazafluorene monomer is represented by the general formula (1) in the figure. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT
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Paragraph 0234-0236
(2020/09/05)
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- Synthesis process of 2-aminoquinazoline compound
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The invention discloses a synthesis process of a 2-aminoquinazoline compound. A purpose of the invention is to solve the problems of high cost, difficult purification, low yield and the like in the prior art. The process comprises the following two steps of: 1, synthesizing o-aminobenzaldehyde, wherein the yield is 96%, the purity is about 95%, and the synthesized o-aminobenzaldehyde can be directly applied to the next step without purification; 2, synthesizing 2-aminoquinazoline, wherein the yield is 50%, the purity is 97.2%, and the comprehensive yield of the reaction in the two steps reaches 48%. The method is simple in process, convenient to operate, stable in reaction, good in reproducibility, low in cost and convenient to purify, and has outstanding substantive features and remarkable progress compared with the prior art.
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Paragraph 0019; 0022; 0025
(2020/06/17)
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- NOVEL PROBE COMPOUNDS FOR FLUORESCENCE AND/OR CIRCULAR DICHROISM SENSOR FOR AMINE COMPOUNDS INCLUDING AMINO ALCOHOLS, AND SIMULTANEOUS ANALYSIS METHOD OF FLUORESCENCE AND CIRCULAR DICHROISM
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The present disclosure relates to a novel probe compound, i.e., 1-(ortho-benzophenylaminoalkyl)-phenylboric acid, or its derivative for a fluorescence and/or circular dichroism (CD) sensor for amine compounds containing aminoalcohols. Also, the present disclosure relates to a simultaneous analysis method of fluorescence and CD of amine compounds containing aminoalcohols using the novel probe compound.
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Paragraph 0109-0110
(2020/12/01)
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- Solvent-free oxidation of benzyl alcohols catalysed by a tetrazole-saccharinate Zn(II) complex under microwave radiation: The role of the ligand and the reaction mechanism
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Herein we present an efficient methodology for the microwave-assisted peroxidative oxidation of benzyl alcohols to the corresponding aldehydes by using a novel and stable tetrazole-saccharinate zinc(II) catalyst, along with some insights into the reaction mechanism. This methodology is distinguished by the use of easily available and cheap reagents on the genesis of the zinc catalyst, mild reaction conditions, very short reaction periods (5–20 min) and no need to add an organic solvent. Furthermore, the use of TBHP (70percent. aq.) as oxidizing agent turn this protocol a convenient one for benzyl alcohol oxidation in yields up to 98percent.
- Cristiano, M. Lurdes S.,Fernandes, André L.,Frija, Luís M. T.,Pombeiro, Armando J. L.
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- Manganese(I)-Catalyzed Sustainable Synthesis of Quinoxaline and Quinazoline Derivatives with the Liberation of Dihydrogen
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Direct synthesis of N-heterocycles via the acceptorless dehydrogenative coupling is very challenging and scarcely reported under 3d transition-metal catalysis. Here, we have developed an efficient Mn(I)-catalyzed sustainable synthesis of various quinoxalines from 1,2-diaminobenzenes and 1,2-diols via the acceptorless dehydrogenative coupling reaction. Further, this strategy was successfully applied for the unprecedented synthesis of quinazolines by the reaction of 2-aminobenzyl alcohol with primary amides. The present protocol provides an atom-economical and sustainable route for the synthesis of various quinoxaline and quinazoline derivatives by employing an earth-abundant manganese salt and simple phosphine-free NNN-tridentate ligand.
- Mondal, Akash,Sahoo, Manoj Kumar,Subaramanian, Murugan,Balaraman, Ekambaram
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p. 7181 - 7191
(2020/07/21)
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- Ionic liquid [Bmim][AuCl4] encapsulated in ZIF-8 as precursors to synthesize N-decorated Au catalysts for selective aerobic oxidation of alcohols
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Here we report a novel approach to synthesize Au NPs immobilized on N-doped carbon materials. In this strategy, an ionic liquid (IL) [Bmim][AuCl4] was selected as the precursor for Au NPs and porous framework of ZIF-8 as the host for the IL. Raman spectroscopy, transmission electron microscopy, N2 physical absorption and Fourier infrared spectra confirmed that the IL was successfully incorporated in the ZIF-8 pores. Followed by a thermal treatment under inert atmosphere, highly dispersed Au NPs were obtained and stabilized by nitrogen species from the carbonization of organic ligand in the metal-organic frameworks (MOFs). The [Bmim][AuCl4]@ZIF-8-6.25percent-T materials exhibited high catalytic activity for the selective aerobic oxidation of alcohols, affording excellent yields (up to >99percent) under atmospheric air and base-free conditions. Catalytic reaction along with catalyst characterization results revealed a strong interaction between Au NPs and N species. TEM, XRD and XPS characterization results further suggested that the N species could not only prevent the Au NPs from aggregation, but also further enhance the reaction activity.
- Chen, Fengfeng,Lu, Qingwen,Fan, Ting,Fang, Ruiqi,Li, Yingwei
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- Self-assembly of mixed-valence and heterometallic metallocycles: efficient catalysts for the oxidation of alcohols to aldehydes in ambient air
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Two mixed-valence CuII/CuIand two heterometallic CuII/AgImetallocycles have been synthesized by the assembly of designed metalloligands and CuI/AgIions, respectively. The CuII/CuImetallocycle can catalyze the oxidation of alcohols to aldehydes mediated by a co-catalyst, TEMPO (2,2,6,6-tetramethylpiperdine-1-oxyl), with ambient air as an oxidant, while the CuII/AgImetallocycle has no catalytic effect.
- Dai, Rui-Rong,Huang, Yong-Liang,Lai, Ya-Liang,Li, Dan,Wang, Xue-Zhi,Zhou, Xian-Chao,Zhou, Xiao-Ping
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supporting information
p. 7304 - 7308
(2020/06/21)
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- Homogeneous Nickel-Catalyzed Sustainable Synthesis of Quinoline and Quinoxaline under Aerobic Conditions
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Dehydrogenative coupling-based reactions have emerged as an efficient route toward the synthesis of a plethora of heterocyclic rings. Herein, we report an efficacious, nickel-catalyzed synthesis of two important heterocycles such as quinoline and quinoxaline. The catalyst is molecularly defined, is phosphine-free, and can operate at a mild reaction temperature of 80 °C. Both the heterocycles can be easily assembled via double dehydrogenative coupling, starting from 2-aminobenzyl alcohol/1-phenylethanol and diamine/diol, respectively, in a shorter span of reaction time. This environmentally benign synthetic protocol employing an inexpensive catalyst can rival many other transition-metal systems that have been developed for the fabrication of two putative heterocycles. Mechanistically, the dehydrogenation of secondary alcohol follows clean pseudo-first-order kinetics and exhibits a sizable kinetic isotope effect. Intriguingly, this catalyst provides an example of storing the trapped hydrogen in the ligand backbone, avoiding metal-hydride formation. Easy regeneration of the oxidized form of the catalyst under aerobic/O2 oxidation makes this protocol eco-friendly and easy to handle.
- Bains, Amreen K.,Singh, Vikramjeet,Adhikari, Debashis
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supporting information
p. 14971 - 14979
(2020/11/30)
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- Self-assembly of a Mixed Valence Copper Triangular Prism and Transformation to Cage Triggered by an External Stimulus
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A triangular prismatic metal-organic cage based on mixed valence copper ions has been designed and synthesized by using metallocycle panels and pillar ligands. The triangular prism will be quickly transformed to a 10-nuclear cage upon an external chemical stimulus, which features a bicapped square antiprism structure. This prismatic cage can act as a catalyst for oxidation of aromatic alcohols to their corresponding aromatic aldehydes with high yields at room temperature under O2 atmosphere.
- Dai, Rui-Rong,Lai, Ya-Liang,Li, Dan,Wang, Xue-Zhi,Zhou, Xian-Chao,Zhou, Xiao-Ping
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p. 17374 - 17378
(2020/11/30)
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- NOVEL PROBE COMPOUNDS FOR FLUORESCENCE AND/OR CIRCULAR DICHROISM SENSOR FOR AMINE COMPOUNDS INCLUDING AMINO ALCOHOLS, AND SIMULTANEOUS ANALYSIS METHOD OF FLUORESCENCE AND CIRCULAR DICHROISM
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The present disclosure relates to a novel probe compound, i.e., 1-(ortho-benzophenylaminoalkyl)-phenylboric acid, or its derivative for a fluorescence and/or circular dichroism (CD) sensor for amine compounds containing aminoalcohols. Also, the present disclosure relates to a simultaneous analysis method of fluorescence and CD of amine compounds containing aminoalcohols using the novel probe compound.
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Paragraph 0142-0145
(2020/12/19)
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- Toward the Rational Design of Universal Dual Polarity Matrix for MALDI Mass Spectrometry
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A series of novel anthranilic acid derivatives I-IV, of which COOH-NH2 (I) and COOH-NHMe (IV) are endowed with acid and base bifunctionality, were designed and synthesized for matrix-assisted laser desorption/ionization time-of-flight (MALDI-TOF) mass spectrometry applications in dual polarity molecular imaging of biological samples, particularly for lipids. The heat of protonation, deprotonation, and proton transfer reaction as well as the capability of analyzing biomolecules in both positive and negative ion modes for I-IV were systematically investigated under standard 355 nm laser excitation. The results indicate correlation between dual polarity and acid-base property. Further, COOH-NHMe (IV) showed a unique performance and was successfully applied as the matrix for MALDI-TOF mass spectrometry imaging (MSI) for studying the mouse brain. Our results demonstrate the superiority of COOH-NHMe (IV) in detecting more lipid and protein species compared to commercially available matrices. Moreover, MALDI-TOF MSI results were obtained for lipid distributions, making COOH-NHMe (IV) a potential next generation universal matrix.
- Chou, Pi-Tai,Hsu, Cheng-Chih,Huang, Chun-Ying,Huang, Penghsuan,Lee, Chuping,Lin, Li-En,Lin, Ta-Chun,Yang, Ethan
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p. 7139 - 7145
(2020/07/21)
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- Rational Design of Phosphorescent Iridium(III) Complexes for Selective Glutathione Sensing and Amplified Photodynamic Therapy
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It is a huge challenge to avoid irreversible damage to normal tissues during irradiation in photodynamic therapy (PDT) for cancer. An effective strategy is to develop smart photosensitizers, which exhibit amplified generation of reactive oxygen species (ROS) through triggering specific reaction in the tumor microenvironment. In this work, we designed a class of glutathione (GSH)-activatable photosensitizers (Ir1 and Ir4) based on an effective strategy of GSH-induced nucleophilic substitution reaction. The addition of GSH, induced changes in both phosphorescence intensity and lifetime of photosensitizers with high sensitivity. Importantly, the amount of singlet oxygen generated was increased significantly by GSH-induced activation reaction. Hence, the photosensitizers can selectively distinguish cancer cells from normal cells through luminescence and lifetime imaging, and can amplify PDT effects in cancer cells, owing to the evidently higher level of GSH compared to normal cells. This work presents a novel paradigm for GSH-amplified PDT against cancer cells and provides a new avenue for smart-responsive theranostic systems that can avoid nonspecific damage to normal cells.
- Huang, Tianci,Yu, Qi,Liu, Shujuan,Zhang, Kenneth Yin,Huang, Wei,Zhao, Qiang
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p. 576 - 586
(2018/11/23)
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- A concise Friedl?nder/Buchwald-Hartwig approach to the total synthesis of quindoline, a bioactive natural indoloquinoline alkaloid, and toward the unnatural 10-methylquindoline
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A new approach toward the synthesis of quindoline, a recognized indoloquinoline alkaloid, is reported. The sequence comprises the synthesis of 2-(2-nitrophenyl)quinoline through an optimized Friedl?nder condensation of 2-amino benzaldehyde with 2-nitroacetophenone, followed by the selective C-3 bromination of the quinoline moiety to direct the cyclization, reduction of the nitro group and a final Buchwald-Hartwig cyclization. In addition, quindoline was also converted to the unnatural 10-methylquindoline by reaction with dimethyl carbonate under DBU promotion. It was found that the non-directed reductive cyclization of 2-(2-nitrophenyl)quinoline results in indazolo[2,3-a]quinoline, instead of yielding quindoline. DFT calculations were employed to explain this reaction outcome; this finding suggested that the result of a previously reported total synthesis of quindoline should be revised.
- Méndez, María V.,Simonetti, Sebastian O.,Kaufman, Teodoro S.,Bracca, Andrea B. J.
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p. 10803 - 10813
(2019/07/15)
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- A novel approach towards chemoselective reduction of nitro to amine
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Chemo selective reduction of a wide range of aromatic nitro compound has been performed by using inexpensive Zn powder and CuSO4 system in water medium at room temperature. This system has high tolerance to other highly reducible groups present in nitro substance along with high conversation and selectivity. This chemo-selective reduction also provides a facile root for the synthesis of other industrially important fine chemicals or biologically important compounds where other highly reducible groups are present in close proximity to the targeted nitro groups.
- Dasgupta, Hridoydip Ranjan,Mukherjee, Suvodip,Ghosh, Pranab
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supporting information
(2019/08/13)
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- Chemoselective reduction of nitroarenes with hydrazine over a highly active alumina-supported cobalt nanocatalyst
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A green and efficient procedure is reported for the chemoselective reduction of nitroarenes catalyzed by a highly active alumina-supported cobalt nanocatalyst in the presence of hydrazine hydrate. The nanocatalyst can be applied under mild reflux conditions for the synthesis of arlyamines in high yields. Moreover, the catalyst can be easily recovered by simple filtration and reused several times without obvious loss in its catalytic activity.
- Albadi, Jalal,Samimi, Heshmat Allah,Jalali, Mehdi
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p. 740 - 744
(2019/10/14)
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- NNN pincer Ru(II)-catalyzed dehydrogenative coupling of 2-aminoarylmethanols with nitriles for the construction of quinazolines
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An efficient NNN pincer Ru(II)-catalyzed preparation of quinazolines via acceptorless dehydrogenative strategy has been developed. Under the optimized conditions, a broad range of substituted o-aminobenzyl alcohols and (hetero)aryl or alkyl nitriles were well tolerated to afford various 2-substituted quinazolines in high yields. Subsequently, a set of control experiments have been performed to elucidate the reaction mechanism, which underwent alcohol oxidation, nitrile hydration, and cyclocondensation steps. The current protocol is featured with several advantages, such as environmental benignity, operational simplicity, broad substrate scope (compatible with aliphatic nitriles, up to 87% yield), and short reaction time (mostly in 2 h).
- Wan, Xiao-Min,Liu, Zi-Lin,Liu, Wan-Qing,Cao, Xiao-Niu,Zhu, Xinju,Zhao, Xue-Mei,Song, Bing,Hao, Xin-Qi,Liu, Guoji
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p. 2697 - 2705
(2019/04/04)
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- A novel nano-cotton-like bismuth oxyfluoride (NC-BiOF) and a novel nanosheet heterogeneous compound BiOF@ZIF-8 as catalyst for the selective and green oxidation of benzylic alcohols
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We describe here for the first time a new morphology of BiOF nanoparticles with a cotton-like structure, made using a hydrothermal synthesis method. We also prepared heterogeneous nanosheets of BiOF@ZIF-8 by a one-pot synthesis under hydrothermal conditions. We demonstrate that in this method the morphology of BiOF and one-pot synthesis conditions are the main factors for the preparation of the nanosheet BiOF@ZIF-8. Fourier transform infrared (FTIR), X-ray diffraction (XRD), scanning electron microscopy (SEM), energy-dispersive X-ray (EDX), thermogravimetry-differential thermal analysis (TG-DTA), and BET surface area were used to characterize the samples prepared. XRD, SEM, and adsorption–desorption analysis showed that the structure of ZIF-8 and BiOF form intact only in one-pot synthesis of BiOF (with nano-cotton-like morphology) with Zn(NO3)3, while spectral techniques show the successful encapsulation of the sheet BiOF on ZIF-8. Nanosheet BiOF@ZIF-8 was found to be a highly efficient heterogeneous catalyst for the selective oxidation of alcohols. BiOF@ZIF-8 could be reused several times although it got less active with recycling.
- Ghayoumian, Narges,Aliyan, Hamid,Fazaeli, Razieh
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p. 363 - 370
(2018/10/26)
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- Copper Nanoparticles Immobilized on Nanocellulose: A Novel and Efficient Heterogeneous Catalyst for Controlled and Selective Oxidation of Sulfides and Alcohols
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In this work, we have described the versatility of low metal loading copper nanoparticles immobilized on nanocellulose for the controlled and selective oxidation of sulfides to sulfoxides and primary alcohols to aldehydes using green oxidant at room temperature. Aromatic, aliphatic and heterocyclic sulfides were oxidized to their corresponding sulfoxides with high yields without formation of over oxidized sulfones. Similarly, benzylic, allylic and aliphatic alcohols were selectively oxidized to aldehydes without traces of carboxylic acids in good to excellent yields.
- Dutta, Apurba,Chetia, Mitali,Ali, Abdul A.,Bordoloi, Ankur,Gehlot, Praveen S.,Kumar, Arvind,Sarma, Diganta
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p. 141 - 150
(2018/12/13)
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- H2-Generation from Alcohols by the MOF-Based Noble Metal-Free Photocatalyst Ni/CdS/TiO2@MIL-101
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The synthesis of important classes of chemical compounds from alcohols helps to conserve Earth's fossil carbon resources, since alcohols can be obtained from indigestible and abundantly available biomass. The utilisation of visible light for the activation of alcohols permits alcohol-based C-N and C-C bond formation under mild conditions inaccessible with thermally operating hydrogen liberation catalysts. Herein, we report on a noble metal-free photocatalyst able to split alcohols into hydrogen and carbonyl compounds under inert gas atmosphere without the requirement of electron donors, additives, or aqueous reaction media. The reusable photocatalyst mediates C-N multiple bond formation using the oxidation of alcohols and subsequent coupling with amines. The photocatalyst consists of a CdS/TiO2 heterojunction decorated with co-catalytic Ni nanoparticles and is prepared on size-optimised colloidal metal-organic framework (MOF) crystallites.
- Tilgner, Dominic,Klarner, Mara,Hammon, Sebastian,Friedrich, Martin,Verch, Andreas,De Jonge, Niels,Kümmel, Stephan,Kempe, Rhett
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p. 842 - 847
(2019/08/26)
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- PdO nanoparticles supported on triazole functionalized porous triazine polymer as an efficient heterogeneous catalyst for carbonylation of aryl halides
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A well-defined triazole functionalized porous triazine based polymers act as solid heterogeneous catalyst after incorporating palladium oxide nanoparticles (PdO@TTAS) have been synthesized and thoroughly characterized by various techniques such as, FT-IR, UV-DRS, solid state 13C CP-MAS, XPS, powder X-ray diffraction, TGA, SEM and TEM analysis has been detailed illustrated. It is important to note that synthesized catalytic performance for carbonylation of aryl halides (X?=?I, Br) with EDC.HCl (N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride), and formic acid was found to be an effective CO source in the presence of triethylamine as a base and DMF as a solvent medium at 80?°C for about 3?hr. The PdO@TTAS catalyst exhibits superior catalytic performance and along with good yield (up to 90%). Moreover, studying the heterogeneity and reusability of the environmentally friendly solid catalyst can be easily separated by simple filtration and then recycled for several times. In this reaction method, we avoided ligand, additive, promoters and CO gas, due to additional problem arise by using gaseous CO, highly toxic greenhouse gases and high pressurized reaction setup.
- Sadhasivam, Velu,Balasaravanan, Rajendran,Siva, Ayyanar
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supporting information
(2019/07/03)
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- Copper-Catalyzed Synthesis of 3-NO2 Quinolines from o-Azidobenzaldehyde and Nitro-olefins and its Application in the Concise Synthesis of Quindolines
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An efficient copper-catalyzed cyclization of o-azidobenzaldehyde and nitro-olefins was developed. This reaction proceeds under solvent-free conditions and displays broad functional group compatibility and affords 3-nitroquinolines in good to excellent yields. The synthetic utility of this strategy is illustrated by the concise construction of quindolines in only three steps, which renders the reaction more practical. (Figure presented.).
- Zheng, Lei,Zeng, Zhigang,Yan, Qiong,Jia, Fengcheng,Jia, Lihui,Chen, Yunfeng
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p. 4037 - 4042
(2018/09/14)
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- Simple and Practical Synthesis of Various New Nickel Boride-Based Nanocomposites and their Applications for the Green and Expeditious Reduction of Nitroarenes to Arylamines under Wet-Solvent-Free Mechanochemical Grinding
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In this paper, we report a simple synthesis of four new nickel boride-based nanocomposites, namely Ni2B@ZrCl4, Ni2B@Cu2O, Ni2B@CuCl2 and Ni2B@FeCl3, from commercially available and cheap starting materials. All of the new Ni2B-based nanocomposites were well characterized by Fourier-transform infrared spectroscopy, X-ray diffraction, scanning electron microscopy, and energy-dispersive X-ray spectroscopy. Further, the catalytic applications of these new nanocomposites were successfully evaluated in the wet-solvent-free reduction of aromatic nitro compounds to arylamines with sodium borohydride (NaBH4) at room temperature by a mechanochemical grinding technique. All the introduced catalytic systems provide excellent yields of arylamines in very short reaction times for a wide range of substrates. Also, recoverability and reusability of the new nanocomposites were investigated.
- Mousavi, Hossein,Zeynizadeh, Behzad,Younesi, Reza,Esmati, Mozhgan
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p. 595 - 609
(2018/09/10)
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- Synthesis method of medical intermediate o-amino benzaldehyde
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The invention discloses a synthesis method of a medical intermediate o-amino benzaldehyde. The synthesis method mainly comprises the following steps: adding 2 mol of o-nitrobenzaldehyde, 50 L of water, 3-4 mol of cuprous chloride and 5-6 mol of 2-aminotol
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Paragraph 0010-0015
(2018/09/08)
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- A high-efficient, rapid synthesis of O-aminobenzaldehyde method
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The invention relates to a method for efficiently and rapidly synthesizing o-amino benzaldehyde from ortho-nitrotoluene under the mild reaction condition by using an environmental-friendly catalyst. The method comprises the step of synthesizing the o-amino benzaldehyde from the ortho-nitrotoluene by taking functionalized ionic liquid as the catalyst and alcohol as solvent under the normal pressure condition and the existence of sodium polysulfide; the ionic liquid has a remarkable catalytic effect; the method is simple in operation and high in yield, and has mild conditions of a catalytic reaction system and a broad industrial application prospect.
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Paragraph 0023-0054
(2018/03/01)
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