- Tertiary amine derivatives and organic electroluminescent device including the same
-
A UV-region high-energy external light source is effectively absorbed to minimize damage to organic materials in the organic electroluminescent device. 1 Is a cross-sectional view of an organic electroluminescence device according to the present invention. O-2 electrode 1 Or more organic material layers disposed between the (2) and (1) th electrodes. A capping layer is included. The organic material layer and/or the capping layer may include the 1 st amine derivative represented by Formula 3. Chemical Formula 1. Wherein each substituent in Formula 1 is as defined in the description of the invention.
- -
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Paragraph 0144-0148
(2021/06/01)
-
- Photocatalytic green synthesis of benzazoles from alcohol oxidation/toluene sp3C-H activation over metal-free BCN: effect of crystallinity and N-B pair exposure
-
Porous borocarbonitride (P-BCN), with the characteristics of enhanced crystallinity and improved N-B pair exposure, was prepared with a simple KCl-assisted molten salt strategy. Efficient heterogeneous photocatalytic tandem synthesis of benzazoles from alcohol oxidation/toluene sp3C-H activation was achieved firstly over the metal-free P-BCN using visible light and the green oxidant O2, with only water as a by-product. Variouso-thio/hydroxy/aminoanilines and alcohols or toluenes could be converted to the corresponding 2-substituted benzothiazoles, benzoxazoles and benzimidazoles with good to excellent photocatalytic performance. The improved photocatalytic performance in comparison to bulk BCN should be due to the crystallinity-enhancement-induced improvement in charge separation and transmission. The increased N-B pair exposure promoted superoxide radical generation due to the electron-enriched N atoms, as well as improved oxidation ability due to the valence band constructed by the B 2p orbital. This work presents a green and efficient synthetic strategy towards benzazoles and other fine chemicalsviametal-free heterogeneous photocatalysis.
- Cheng, Hongmei,Gao, Xue,Jiang, Heyan,Sun, Bin,Zang, Cuicui
-
p. 7955 - 7962
(2021/12/27)
-
- A TEMPO-Functionalized Ordered Mesoporous Polymer as a Highly Active and Reusable Organocatalyst
-
The properties of high stability, periodic porosity, and tunable nature of ordered mesoporous polymers make these materials ideal catalytic nanoreactors. However, their application in organocatalysis has been rarely explored. We report herein for the first time the incorporation of a versatile organocatalyst, 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO), into the pores of an FDU-type mesoporous polymer via a pore surface engineering strategy. The resulting FDU-15-TEMPO possesses a highly ordered mesoporous organic framework and enhanced stability, and shows excellent catalytic activity in the selective oxidation of alcohols and aerobic oxidative synthesis of 2-substituted benzoxazoles, benzimidazoles and benzothiazoles. Moreover, the catalyst can be easily recovered and reused for up to 7 consecutive cycles.
- Guo, Ying,Wang, Wei David,Li, Shengyu,Zhu, Yin,Wang, Xiaoyu,Liu, Xiao,Zhang, Yuan
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p. 3689 - 3694
(2021/09/29)
-
- Delivering 2-Aryl Benzoxazoles through Metal-Free and Redox-Neutral De-CF3Process
-
An unexpected cleavage of the Csp3-CF3 bond of CF3-hydrobenzoxazoles has been disclosed, affording a range of 2-aryl benzoxazoles under metal-free and redox-neutral conditions. This transformation has demonstrated broad substrate scope and good compatibility of functional groups. 2-Aryl benzothiazole and 2-aryl benzoimidazole could be smoothly assembled in the same manner. On the basis of preliminary mechanistic studies, base initiated and aromatization driven β-carbon elimination was considered to be the key step for the formation of 2. This reaction offers an alternative, facile, and sustainable route to access important 2-aryl benzoxazole motifs.
- Qiao, Xinxin,Zhao, Yong-De,Rao, Mingru,Bu, Zhan-Wei,Zhang, Guangwu,Xiong, Heng-Ying
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p. 13548 - 13558
(2021/10/01)
-
- Acetyl nitrate mediated conversion of methyl ketones to diverse carboxylic acid derivatives
-
The development of a novel acetyl nitrate mediated oxidative conversion of methyl ketones to carboxylic acid derivatives is described. By analogy to the haloform reaction and supported by experimental and computational investigation we propose a mechanism for this transformation.
- Bernard, Josephine,Capilato, Joseph N.,Hoy, Erik P.,Mattiucci, Joseph,Pellegrinelli, Peter J.,Perez, Lark J.,Philippi, Shane,Schnorbus, Logan
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p. 5298 - 5302
(2021/06/30)
-
- Organic compound taking carbazole as core and organic electroluminescent device containing organic compound
-
The invention relates to an organic compound taking carbazole as a core and an organic electroluminescent device containing the organic compound. The compound provided by the invention has relativelyhigh glass transition temperature and molecular thermal stability; the refractive index in the field of visible light is high, and the light extraction efficiency of an OLED device can be effectivelyimproved after the compound is applied to a CPL layer of the OLED device; and the organic electroluminescent device is higher in light-emitting efficiency, better in visual declination angle, better in inhibition of angle dependence of emergent light wavelength and high in yield.
- -
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Paragraph 0070-0073
(2021/02/10)
-
- An electroluminescent compound and an electroluminescent device comprising the same
-
The present invention relates to a novel organic light emitting compound represented by chemical formula I, which is used as a material of an organic material layer such as a light emitting layer, a hole transport layer, an electron transport layer, an electron blocking layer, and a light efficiency improvement layer in an organic light emitting device, and thus can realize luminous properties such as remarkably excellent luminous efficiency and quantum efficiency. The present invention also relates to the organic light emitting device comprising the novel organic light emitting compound.
- -
-
Paragraph 0215; 0220-0222
(2021/02/05)
-
- An efficient rapid synthesis of benzoxazoles and benzothiazoles using pma.Sio2 at room temperature under heterogeneous conditions
-
Treatment of 2-aminophenol (or 2-aminothiophenol) with aromatic aldehydes in the presence of phosphomolybdic acid on silica at room temperature affords the corresponding benzoxazoles (or benzothiazoles) in excellent yields (88-96%) under heterogeneous conditions. Benzoxazoles and benzothiazoles are formed in less than 10 min.
- Sudhakar, Chithaluri,Shekhar, Vanam,Shyamsunder, Manchi,Suryakumari, Adurthi,Manojkumar, Vala
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p. 583 - 587
(2021/09/30)
-
- Dowex 50W: A green mild reusable catalyst for the synthesis of 2-aryl benzoxazole derivatives in aqueous medium
-
In this work simple efficient, one pot and environmentally friendly method was developed for the synthesis of 2-Aryl-1H-benzoxazole derivatives at 80oC using ortho-aminophenol and various aldehydes. It has been found that Dowex 50W is an effective catalyst to prepare moderate to high yield of a variety of benzoxazole derivatives through a clean and simple process. Aqueous medium, green methodology, rapid reaction, reusability of heterogeneous catalyst are the great advantages of this protocol.
- Datta, Arup
-
p. 341 - 347
(2021/05/19)
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- Heterogeneous palladium (II)-complexed dendronized polymer: A rare palladium catalyst for the one-pot synthesis of 2-arylbenzoxazoles
-
The palladium complex of dendronized amine polymer (EG–Gn–Pd, n = 0, 1 and 2) having ethylene glycol-initiated polyepichlorohydrin as core was synthesized on a Merrifield resin support and was well characterized. Generally, palladium catalysts are known for carbon–carbon coupling reactions. Here, a developed catalyst was found to be good for benzoxazole synthesis. Higher generation dendronized polymer (EG–G2–Pd) was found to be better catalyst over lower generation dendronized polymers. Moreover, dendronized polymers were found to be a better catalyst over dendrigraft polymers. The catalyst reusability was checked and good yield was obtained for five cycles.
- George, Smitha,Sreekumar, Krishnapillai
-
-
- Syntheses, characterization, and catalytic potential of novel vanadium and molybdenum Schiff base complexes for the preparation of benzimidazoles, benzoxazoles, and benzothiazoles under thermal and ultrasonic conditions
-
A new ONO-tridentate Schiff base ligand (H2L) derived from 3-methoxysalicylaldehyde and nicotinic hydrazide was synthesized and characterized by elemental analysis, FT-IR, 1H NMR, 13C NMR, UV–Vis, and powder XRD studies. Then, oxovanadium(V) and dioxomolybdenum(VI) Schiff base complexes, VOL and MoO2L, were also prepared and characterized by different techniques. Moreover, the catalytic activities of both complexes were investigated for the synthesis of benzimidazoles, benzoxazoles, and benzothiazoles under reflux conditions as well as through ultrasonic irradiation. The results revealed several advantages of this procedure, including high product yields, short reaction times, facile work-up procedure, simplicity in operation, eco-friendly reaction conditions, and green aspects by avoiding toxic catalysts and solvents. Graphic abstract: [Figure not available: see fulltext.]
- Kargar, Hadi,Kargar, Khadijeh,Fallah-Mehrjardi, Mehdi,Munawar, Khurram Shahzad
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p. 593 - 605
(2021/06/21)
-
- 4-benzo five-membered ring-phenyl ketoxime ester compound as well as preparation method and application thereof
-
The invention discloses a 4-benzo five-membered ring- phenyl ketoxime ester compound as well as a preparation method and application thereof. The invention relates to a 4-benzo five-membered ring-phenyl oxime ester derivative shown as a formula (I), a photocuring composition and a preparation method of the 4-benzo five-membered ring-phenyl ketoxime ester derivative shown as the formula (I). The 4-benzo five-membered ring-phenyl ketoxime ester derivative molecule represented by the formula (I) has the advantages of red shift of absorption wavelength, good photoinitiation efficiency, simple synthesis steps, and wide application prospect in the field of UV-Vis-LED excitable photocureable coating or ink industrialization.
- -
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Paragraph 0126-0129
(2021/02/10)
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- Facile access to libraries of diversely substituted 2-aryl-benzoxazoles/benzothiazoles from readily accessible aldimines via cyclization/cross coupling in imidazolium-ILs with Pd(OAc)2 or NiCl2 (dppp) as catalyst
-
A two-step protocol involving Pd-catalyzed cyclization of readily accessible p-bromophenyl-aldimines to 2-bromophenyl-benzoxazole/benzothiazole in [BMIM][PF6] or [BMIM][BF4] as solvent, followed by the Suzuki, Heck, and Sonogashira cross-coupling reactions catalyzed by Pd or Ni is described that generates libraries of diversely substituted 2-aryl-/heteroaryl-benzoxazoles/benzothiazoles in respectable isolated yields under mild reaction conditions. The feasibility to perform the two-steps in sequence in one-pot starting from the aldimines is also demonstrated and the potential for recycling/reuse of the IL solvent is also shown.
- Malunavar, Shruti S.,Sutar, Suraj M.,Savanur, Hemantkumar M.,Kalkhambkar, Rajesh G.,Laali, Kenneth K.
-
supporting information
(2019/12/24)
-
- ORGANIC ELECTROLUMINESCENT COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE INCLUDING THE SAME
-
Disclosed is a novel organic electroluminescent compound represented by Formula (I): The organic electroluminescent compound is employed as a material for at least one organic layer of an organic electroluminescent device such as a light emitting layer, a hole transport layer, an electron transport layer, an electron blocking layer, and/or a capping layer, achieving excellent luminescent properties (including high luminous efficiency and quantum efficiency) of the device. Also disclosed is an organic electroluminescent device including the organic electroluminescent compound.
- -
-
Paragraph 0092-0093
(2020/12/13)
-
- Visible Light-Induced Copper-Catalyzed C—H Arylation of Benzoxazoles?
-
A general method for visible light-induced copper-catalyzed arylation of sp2 C—H bonds of azoles has been developed. The method employs aryl halide as the coupling partner, lithium alkoxide as base. A variety of azoles including benzooxazole and benzothiazole can be arylated. Furthermore, electron-poor heterocycles such as thiophene possessing one electron-withdrawing group can also be arylated.
- Ma, Xiaodong,Zhang, Guozhu
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p. 1299 - 1303
(2020/08/05)
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- Iron(0)-Catalyzed Transfer Hydrogenative Condensation of Nitroarenes with Alcohols: A Straightforward Approach to Benzoxazoles, Benzothiazoles, and Benzimidazoles
-
The iron-catalyzed hydrogen transfer strategy has been applied to the redox condensation of o-hydroxynitrobenzene with alcohol, leading to the formation of benzoxazole derivatives. A wide range of 2-substituted benzoxazoles were synthesized in good to excellent yields without the addition of an external redox agent. A series of control experiments provided a plausible mechanism. Furthermore, the reaction system was successfully extended to the synthesis of benzothiazoles and benzimidazoles.
- Putta, Ramachandra Reddy,Chun, Simin,Choi, Seung Hyun,Lee, Seok Beom,Oh, Dong-Chan,Hong, Suckchang
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p. 15396 - 15405
(2020/12/02)
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- Efficient Cu-catalyzed intramolecular: O -arylation for synthesis of benzoxazoles in water
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An efficient method was developed for synthesis of benzoxazoles by Cu-catalyzed intramolecular O-arylation of o-halobenzanilides in water. This strategy provides several advantages, such as high yields, water as a green solvent and functional groups tolerance.
- Gao, Hui,Li, Minxin,Mao, Zewei,Rao, Gaoxiong,Tang, Yanling
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p. 14317 - 14321
(2020/04/23)
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- Compound constituting a hole transfer layer and an electron transfer layer of an organic light emitting diode or a method for producing the same
-
The present invention relates to a compound constituting a hole transport layer and an electron transport layer of an organic light emitting diode, or a method for manufacturing the same. According to the present invention, it is possible to provide a plurality of compounds having excellent yields and excellent purity constituting the hole transport layer and the electron transport layer. An object of the present invention is to provide the compound constituting the hole transport layer and the electron transport layer of the organic light emitting diode, or the method for manufacturing the same.(AA) HPLC analysis result of a final productCOPYRIGHT KIPO 2020
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Paragraph 0132-0134
(2020/09/16)
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- Development of homogeneous polyamine organocatalyst for the synthesis of 2-aryl-substituted benzimidazole and benzoxazole derivatives
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A new polyamine was prepared by the ring opening polymerization of epichlorohydrin and properly characterized. The catalytic property of the prepared polymer was assessed by synthesizing 2-aryl-substituted benzimidazole and benzoxazole derivatives by the conjugation of o-phenylenediamine/o-aminophenol with various aromatic aldehydes in the presence of atmospheric oxygen. Significant attributes of the present synthesis include short reaction time, good to excellent yield, high purity, easy reusability, and room temperature reaction. The reaction was carried out in the absence of any metal catalyst and other cooxidants.
- Kottayil, Hiba,Machingal, Shaibuna,Parackal B., Sherly mole,Alungal M., Shebitha,Theresa, Letcy V.,Govindan, Avudaiappan,Krishnapillai, Sreekumar
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p. 3310 - 3317
(2020/07/17)
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- Synthesis and X-ray crystal structures of three new nickel(II) complexes of benzoylhydrazones: Catalytic applications in the synthesis of 2-arylbenzoxazoles
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Three new complexes of nickel(II), having general formula [Ni(L1)(PPh3)] (1), [Ni(L1)(4-picoline)] (2), and [Ni(L2)(4-picoline)] (3) were synthesized by the reaction of Ni(OAc)2·4H2O with corresponding benzolyhydrazine-derived Schiff base ligands i.e. [4-(diethylamino)-2-hydroxybenzylidene]-benzohydrazonic acid (H2L1) or [2-(hydroxynaphthalen-1-yl)methylene]-benzohydrazonic acid (H2L2) and PPh3/4-picoline as co-ligand in 1:1:1 ratio in methanol. All the three complexes were air-stable, isolated as reddish brown solids and characterized by Elemental analysis, FT-IR, 1H, 13C{1H}, 31P{1H} NMR spectroscopy and mass spectrometry. The structures of all three complexes were determined by single crystal X-ray diffraction studies which revealed the distorted square planar geometry of the complexes. In these complexes, three coordination sites were occupied by ONO pincer type Schiff base ligand and the fourth site was blocked by phosphorus (P) or nitrogen (N) atom of the co-ligand. The catalytic potential of all three complexes was explored in the synthesis of a series of 2-arylbenzoxazoles from aldehydes and 2-aminophenol, using low catalyst loading (0.5 mol%). Complex 1 was found to be the best catalyst among three complexes, for the synthesis of a series of 2-aryl benzoxazoles. The ease of synthesis, air-stability and robustness of the catalyst, and good TONs are some of the key characteristics of the described catalytic system.
- Layek, Samaresh,Agrahari, Bhumika,Kumar, Akash,Dege, Necmi,Pathak, Devendra D.
-
-
- Sulfur-Promoted Synthesis of Benzoxazoles from 2-Aminophenols and Aldehydes
-
Elemental sulfur (S8) was found to be an excellent stoichiometric oxidant to promote oxidative condensation of 2-aminophenols with a wide range of aldehydes, including aliphatic aldehyde such as cyclohexanecarboxaldehyde. The reactions were catalyzed by sodium sulfide in the presence of DMSO as an additive. The benzoxazole products were obtained in satisfactory yields. The reaction conditions could be applied to larger syntheses (10–50 mmol).
- Nguyen, Le Anh,Dang, Thai Duy,Ngo, Quoc Anh,Nguyen, Thanh Binh
-
supporting information
p. 3818 - 3821
(2020/06/10)
-
- Oxidative NHC catalysis for base-free synthesis of benzoxazinones and benzoazoles by thermal activated NHCs precursor ionic liquid catalyst using air as oxidant
-
A reusable thermal activated NHC precursor ionic liquid catalyst ([BMIm]2[WO4]) has been prepared and developed for the synthesis of nitrogen-containing heterocycles such as benzoxazinones and benzoazoles through imines activation. [BMIm]2[WO4] exhibited the good activity for the base-free condensation and oxidative NHC catalysis tandem under air atmosphere. The catalyst can be recovered and reused for at least five runs in gram scale synthesis without any decrease in catalytic activity. Furthermore, the control experiments demonstrated that the reaction involved formation of aromatic aldimines, NHC-catalyzed oxidative formation of imidoyl azoliums and intramolecular cyclization to generate the product.
- Guan, Jiali,Liu, Wei,Liu, Yuchen,Song, Zhibin,Tao, Duan-Jian,Yan, Jieying,Yuan, Jian-Jun,Zhou, Youkang
-
-
- In-vitro Anti-cancer assay and apoptotic cell pathway of newly synthesized benzoxazole-N-heterocyclic hybrids as potent tyrosine kinase inhibitors
-
A series of benzoxazole-N-heterocyclic hybrids have been synthesized by a one-pot strategy. Molecular docking study revealed that such compounds have the ability to inhibit enzyme protein tyrosine kinase. The findings of this work have been the successful synthesis of benzoxazole scaffolds, featuring hybrids of benzoxazole with quinoline and quinoxaline respectively. The molecular docking studies have showed these compounds to be inhibitors of tyrosine kinase enzyme which triggers growth of cancer cells. The cytotoxicity study of compounds 4a-f showed better potency against breast cancer cell lines MCF-7 and MDA-MB-231 in contrast to oral and lung cancer cell lines KB and A549. The tyrosine kinase activity was measured using Universal Tyrosine Kinase Assay kit using horseradish peroxide (HRP)-conjugated anti-phosphotyrosine kinase solution as a substrate. The compounds 4c exhibited maximum inhibition in the activity of enzyme tyrosine kinase with IC50 value 0.10 ± 0.16 μM, than other compounds which were studied and thus proved to be inhibitors of enzyme tyrosine kinase. The selective index of all four compounds was found out to be greater than two, indicating the non-toxic behaviour, i.e. good anti-cancer activity. Further, fluorescence microscopic study helped to characterize the mode of cell death, which was found to be late apoptosis as indicated by the orange fluorescence. The SAR analysis has also been carried out.
- Desai, Sulaksha,Desai, Vidya,Shingade, Sunil
-
supporting information
(2019/11/13)
-
- Method for synthesizing benzoxazole through microwave radiation of benzamide compound in water phase
-
The invention discloses a method for synthesizing benzoxazole through microwave radiation of a benzamide compound in a water phase. The benzamide compound is added into the water phase under the microwave condition to be subjected to a cyclization reaction for generating the benzoxazole under the alkali condition, and the method for preparing the benzoxazole is environmentally friendly, easy and convenient to operate, safe, low in cost and efficient. Compared with the prior art, the method can be applied to a large number of functional groups, the yield is high, the number of by-products is small, and the method is easy to operate, safe, low in cost and environmentally friendly. (Please see the specifications for the formula).
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-
Paragraph 0057
(2019/03/08)
-
- Method used for rapid preparation of benzo-heterocycle compound with physical grinding under solvent-free room temperature conditions
-
The invention discloses a method used for rapid preparation of benzo-heterocycle compound with physical grinding under solvent-free room temperature conditions. According to the method, glacial aceticacid is taken as a catalyst; at solvent-free room temperature conditions, physical grinding is adopted, reaction of 2-substituted arylamines (2-mercapto arylamine, 2-aminophenol, and o-phenylenediamine) and aromatic aldehydes is carried out using physical grinding. The method is friendly to the environment, is simple in operation, is safe, is low in cost, and is high in efficiency. Compared withthe prior art, the advantages are that: the method is suitable for a large amount of functional groups, yield is high, less by-product is generated, operation is simple, the method is safe, cost is low, and the method is friendly to the environment.
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-
Paragraph 0062; 0075
(2019/01/21)
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- Tribenzazole amine derivatives and organic electroluminescent device including the same
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The present invention provides a tribenzazole amine derivative which contributes to substantial life improvement of an organic electroluminescent device by effectively absorbing a high energy external light source of an UV area and minimizing the damage of organic materials in the organic electroluminescent device. The organic electroluminescent device according to the present invention includes: a first electrode; a second electrode; an organic material layer disposed between the first electrode and the second electrode; and a capping layer disposed on the second electrode. The capping layer includes a tribenzazole amine derivative represented by chemical formula 1. In chemical formula 1, R^1, R^2 and R^3 are the same as or different from each other and are respectively and independently hydrogen and an alkyl group having 1 to 10 carbon atoms. l, n, and m are integers of 0 to 4.COPYRIGHT KIPO 2020
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Paragraph 0136; 0140
(2020/01/31)
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- Tertiary amine derivatives and organic electroluminescent device including the same
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Provided is a tertiary amine derivative which contributes to a substantial increase in service life of an organic electroluminescent device by minimizing damages to organic matter inside the organic electroluminescent device via effective absorption of a high-energy external light source in the UV region. According to the present invention, the organic electroluminescent device comprises: a first electrode and a second electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein the organic material layers comprise a tertiary amine derivative represented by chemical formula 1. In the chemical formula 1, Z_1, Z_2, and Z_3 are each independently O or S.COPYRIGHT KIPO 2020
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Paragraph 0178; 0179; 0182
(2020/02/01)
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- Aryl amine derivatieves and organic electroluminescent device including the same
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Provided is an arylamine derivative that effectively absorbs a high-energy external light source in a UV region and minimizes damage to organic matter inside an organic electroluminescent device, thereby contributing to a substantial improvement in the lifespan of the organic electroluminescent device. An organic electroluminescent device according to the present invention comprises a first electrode, a second electrode, and one or more organic material layers provided between the first electrode and the second electrode. The organic material layer contains an arylamine derivative representedby chemical formula 1. In the chemical formula 1, the definition of each substituent is the same as the definition in the specific embodiment of the invention.
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-
Paragraph 0131; 0132; 0134
(2019/08/12)
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- Aryl amine derivatieves and organic electroluminescent device including the same
-
Provided is an arylamine derivative effectively absorbing a high energy external light source of an ultraviolet (UV) region to minimize damage to organic materials in an organic electroluminescent device so as to contribute to substantial life extension of the organic electroluminescent device. According to the present invention, the organic electroluminescent device comprises: a first electrode; an organic film disposed on the first electrode; a second electrode disposed on the organic film; and a capping layer disposed on the second electrode. Moreover, the organic film and/or the capping layer include an arylamine derivative represented by chemical formula 1, wherein each substituent is the same as in the detailed description.COPYRIGHT KIPO 2019
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Paragraph 0209; 0210; 0213
(2019/12/25)
-
- Iodine Promoted One-Pot Synthesis of 2-Aryl Benzoxazoles from Amidoximes via Oxidative Cyclization and Ring Contraction
-
A molecular I2-promoted one-pot synthesis of 2-aryl benzoxazoles has been developed by using amidoximes rather than the limited 2-aminophenols or 2-haloamides as substrates. The amidoxime substrates provided unique and efficient strategies for converting readily available aniline and benzaldehyde precursors into valuable chemicals. This transformation proceeded smoothly under transition-metal-free conditions through a sequential oxidative cyclization and ring contraction, and provided a potential route for introducing certain groups at any site of the scaffold.
- Zhang, Yong,Ji, Min
-
supporting information
p. 7506 - 7510
(2019/11/28)
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- Transition-Metal-Free Alkylation/Arylation of Benzoxazole via Tf2O-Activated-Amide
-
A transition-metal-free approach to the alkylation/arylation of benzoxazole was developed by employing Tf2O-activated-amide as the alkylating/arylating reagent. The mild reaction conditions, and particularly insensitivity to air and water, further enhance the synthetic potential in pharmaceutical synthesis. (Figure presented.).
- Niu, Zhi-Jie,Li, Lian-Hua,Liu, Xue-Yuan,Liang, Yong-Min
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p. 5217 - 5222
(2019/11/13)
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- Preparation method of 2-(4-bromophenylacetone)-1,3-benzoxazole
-
The invention discloses a preparation method of 2-(4-bromophenylacetone)-1,3-benzoxazole, and belongs to the field of organic synthesis. According to the preparation method of the 2-(4-bromophenylacetone)-1,3-benzoxazole, the synthesis path is shown in the specification. According to the preparation method of the 2-(4-bromophenylacetone)-1,3-benzoxazole, adopted raw materials are cheap and easy to obtain, the cost is low, the technologic operation is convenient, no ultrahigh temperature special equipment needs to be adopted, safety is high, the total yield is high, and the method is environmentally friendly.
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-
-
- A New Pathway to 2-Arylbenzoxazoles and 2-Arylbenzothiazoles Via One-Pot Oxidative Cyclization Reactions Under Iron-Organic Framework Catalysis
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Iron-organic framework MOF-235 was synthesized, and consequently utilized as a productive heterogeneous catalyst for the synthesis of 2-arylbenzoxazoles and 2-arylbenzothiazoles via one-pot oxidative cyclization reactions between 2-aminophenols or 2-aminothiophenols and alcohols. The transformation was considerably controlled by the oxidant and the nature of solvent, and the system of di-tert-butylperoxide with xylene led to best yield of major products. The MOF-235 catalyst presented higher catalytic efficiency for the synthesis of 2-arylbenzoxazoles and 2-arylbenzothiazoles than a number of MOF-based catalysts and established homogeneous catalysts. Recovering and reutilizing the framework catalyst for the cyclization transformation was possible while its catalytic activity was retained. To the best of our knowledge, this iron-catalyzed one-pot oxidative transformation to produce 2-arylbenzoxazoles and 2-arylbenzothiazoles under heterogeneous catalysis conditions was not previously reported in the literature.
- Doan, Son H.,Tran, Chau B.,Cao, An. L. N.,Le, Nhan T. H.,Phan, Nam T. S.
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p. 2053 - 2063
(2019/04/25)
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- Organic light-emitting material, preparing method thereof and organic light-emitting device
-
The invention discloses an organic light-emitting material, a preparing method thereof and an organic light-emitting device. The organic light-emitting material comprises oxadiazole benzodioxazole. The organic light-emitting material comprises the oxadiazole benzodioxazole, has high planarity and strong visible pi-pi* absorption capacity and meanwhile has high-quantum-yield fluorescent transmission capacity; thus, the oxadiazole benzodioxazole with a large pi conjugation system has the efficient electronic transmission characteristic, can increase the charge migration efficiency as an efficient electron withdrawing group and effectively improves the light-emitting efficiency of the organic light-emitting device.
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-
Paragraph 0033-0034
(2019/10/01)
-
- Synthesis of Benz-Fused Azoles via C-Heteroatom Coupling Reactions Catalyzed by Cu(I) in the Presence of Glycosyltriazole Ligands
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Glycosyl triazoles are conveniently accessible and contain multiple metal-binding units that may assist in metal-mediated catalysis. Azide derivatives of d-glucose have been converted to their respective aryltriazoles and screened as ligands for the synthesis of 2-substituted benz-fused azoles and benzimidazoquinazolinones by Cu-catalyzed intramolecular Ullmann type C-heteroatom coupling. Good to excellent yields for a variety of benz-fused heterocyles were obtained for this readily accessible catalytic system.
- Mishra, Nidhi,Singh, Anoop S.,Agrahari, Anand K.,Singh, Sumit K.,Singh, Mala,Tiwari, Vinod K.
-
supporting information
p. 389 - 399
(2019/05/06)
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- Oxidative NHC Catalysis for the Generation of Imidoyl Azoliums: Synthesis of Benzoxazoles
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N-Heterocyclic carbene (NHC)-catalyzed intramolecular cyclization of aldimines generated from 2-amino phenols and aromatic aldehydes leading to the synthesis of 2-arylbenzoxazoles under mild conditions is presented. The reaction proceeds via the generation of the aza-Breslow intermediates from imines and NHC, which under oxidative conditions form the key imidoyl azoliums and a subsequent intramolecular cyclization furnishes the product. The reaction tolerates a broad range of functional groups, and the products are formed in generally good yields.
- Patra, Atanu,James, Anjima,Das, Tamal Kanti,Biju, Akkattu T.
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p. 14820 - 14826
(2019/01/03)
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- Synthesis and characterization of a novel oxo-bridged binuclear iron(iii) complex: Its catalytic application in the synthesis of benzoxazoles using benzyl alcohol in water
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In the present work, the synthesis and characterization of a novel binuclear oxo-bridged iron(iii) complex, (FeLAPIP)2O, where LAPIP is the deprotonated form of a tetradentateo-aminophenol-iminopyridine ligand, is described. The iron complex was characterized using different techniques including X-ray crystallography, infrared spectroscopy, UV-Vis, magnetic susceptibility and cyclic voltammetry. The X-ray structure analysis revealed that in the structure of the (FeLAPIP)2O complex, each iron(iii) is coordinated in a distorted square pyramidal arrangement by an oxo group, three amine nitrogens and one oxygen atom of the o-aminophenolate ligand. The variable-temperature magnetic measurement exhibits strong antiferromagnetic coupling between two iron(iii) centers. Cyclic voltammetry measurements showed two kinds of quasireversible events, suggesting the formation of a phenoxyl radical species in the region of the anodic peaks and a metal-centered redox (FeIII/FeII) process at low potential. The catalytic activity of this Fe-complex was evaluated in coupling of 2-aminophenol and benzyl alcohols for the one-pot synthesis of benzoxazoles. The catalyst system showed high catalytic activity in this transformation and benzoxazole derivatives were obtained in good to excellent yields. tert-Butyl hydroperoxide was used as an oxidant and 1.2 mol% of catalyst was needed to accomplish the reaction in water as the green solvent.
- Safaei, Elham,Alaji, Zahra,Panahi, Farhad,Wojtczak, Andrzej,Jagli?i?, Janez Zvonko
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supporting information
p. 7230 - 7236
(2018/05/07)
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- Synthesis and characterization of amino glucose-functionalized silica-coated NiFe2O4 nanoparticles: A heterogeneous, new and magnetically separable catalyst for the solvent-free synthesis of 2,4,5–trisubstituted imidazoles, benzo[d]imidazoles, benzo[d] oxazoles and azo-linked benzo[d]oxazoles
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Amino glucose-functionalized silica-coated NiFe2O4 nanoparticles (NiFe2O4@SiO2@amino glucose) were chemically synthesized and characterized by transmission electron microscope (TEM), X-ray diffraction (XRD), thermal gravimetric analysis (TGA), energy dispersive X-ray analysis (EDX), vibrating sample magnetometer (VSM), Zetasizer and Fourier transform infrared spectroscopy (FT-IR) instruments. NiFe2O4@SiO2@amino glucose supply an environmentally friendly procedure for the synthesis of 2,4,5-trisubstituted imidazoles through one-pot multicomponent condensation of benzil or benzoin, ammonium acetate with aryl aldehydes and for the synthesis of benzoxazoles using condensation reaction of 2-aminophenol with aryl aldehydes under solvent free condition. In the other study, this synthesized magnetically reusable catalyst was introduced as a new avenue for the synthesis of benzo[d]imidazoles using the reaction between aryl aldehydes and 1,2-diaminobenzene. These compounds were obtained in high yields and short reaction times. The catalyst could be easily recovered and reused for five cycles with almost consistent activity. Synthesized compounds were characterized by their physical constant, comparison with authentic samples, FT-IR, 1H NMR, 13C NMR spectroscopy and elemental analysis.
- Fekri, Leila Zare,Nikpassand, Mohammad,Shariati, Shahab,Aghazadeh, Behnaz,Zarkeshvari, Reza,Norouz pour, Nahid
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- N-Heterocyclic Carbene (NHC)-Catalyzed One-Pot Aerobic Oxidative Synthesis of 2-Substituted Benzo[ d ]oxazoles, Benzo[ d ]thiazoles and 1,2-Disubstituted Benzo[ d ]imidazoles
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N-Heterocyclic carbene (NHC), generated in situ from easily available N-heterocyclic imidazolium salt with air as terminal oxidant, has successfully been utilized as a cheap and efficient catalyst for one-pot aerobic oxidative synthesis of 2-arylbenzo[ d ]oxazoles, 2-substituted benzo[ d ]thiazoles, and 1,2-disubstituted benzo[ d ]imidazoles.
- Zhou, Quan,Liu, Shu,Ma, Ming,Cui, He-Zhen,Hong, Xi,Huang, Shuang,Zhang, Jing-Fan,Hou, Xiu-Feng
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supporting information
p. 1315 - 1322
(2018/03/10)
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- OMS-2/H2O2/Dimethyl Carbonate: An Environmentally-Friendly Heterogeneous Catalytic System for the Oxidative Synthesis of Benzoxazoles at Room Temperature
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A manganese octahedral molecular sieve (OMS-2) was found to be an efficient and recyclable heterogeneous catalyst for the oxidative synthesis of benzoxazoles in the gram-scale from phenolic imines at room temperature. H2O2 and biobased reagent dimethyl carbonate (DMC) were successfully employed as the environmentally friendly oxidant and solvent, respectively, in an OMS-2-catalysted redox reaction for the first time. Benzoxazoles could also be obtained from N-substituted 2-aminophenols via Cu(OH)x/OMS-2-catalyzed sequential oxidative transformation at elevated temperatures.
- Meng, Xu,Wang, Yuanguang,Chen, Baohua,Chen, Gexin,Jing, Zhenqiang,Zhao, Peiqing
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supporting information
p. 2018 - 2024
(2017/12/26)
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- pyrimidine derivatives substituted with aryl- or heteroaryl- substituted fluorene group, and organic electroluminescent device including the same
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Aryl group or a heteroaryl group substituted pyrimidine derivatives of formula 1 is coupled to polyarylenic backbone containing encoded ball number. [Formula 1] [In said formula 1, Ar1 And Ar2 Are each independently a hydrogen, methyl or phenyl, The C L6 - C24 C aryl of reflector3 - C24 It will be biting and heteroatoms, N is an integer 0 or 1 and, Ar3 The C6 - C30 C aryl of reflector3 - C30 A variety of printers] (by machine translation)
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Paragraph 0151; 0152; 0155; 0156
(2017/10/28)
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- Fused phenanthridine derivatives substituted with aryl or heteroaryl, and organic electroluminescent device including the same
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Aryl group or a heteroaryl group substituted [...] phenanthridine derivatives of formula 1 to ball number encoded. [Formula 1] [In said formula 1, Ar1 Is phenyl or pyridyl [...], Z1 And the O or S, L is a phenyl or pyridyl [...], Ar2 To is selected from the group represented by either formula 3] [Formula 3] , , , , (by machine translation)
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Paragraph 0361-0362; 0365-0366
(2018/03/28)
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- Synthesis of Benzoxazoles Using Electrochemically Generated Hypervalent Iodine
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The indirect ("ex-cell") electrochemical synthesis of benzoxazoles from imines using a redox mediator based on the iodine(I)/iodine(III) redox couple is reported. Tethering the redox-active iodophenyl subunit to a tetra-alkylammonium moiety allowed for anodic oxidation to be performed without supporting electrolyte. The mediator salt can be easily recovered and reused. Our "ex-cell" approach toward the electrosynthesis of benzoxazoles is compatible with a range of redox-sensitive functional groups. An unprecedented concerted reductive elimination mechanism for benzoxazole formation is proposed on the basis of control experiments and DFT calculations.
- Koleda, Olesja,Broese, Timo,Noetzel, Jan,Roemelt, Michael,Suna, Edgars,Francke, Robert
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p. 11669 - 11681
(2017/11/24)
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- Oxidative Synthesis of Benzimidazoles, Quinoxalines, and Benzoxazoles from Primary Amines by ortho-Quinone Catalysis
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The bioinspired ortho-quinone catalysts have been applied to heterocycles synthesis. Without any metal cocatalysts, a sole ortho-quinone catalyst enables the oxidative synthesis of benzimidazoles, quinoxalines and benzoxazoles from primary amines in high yields under mild conditions with oxygen as the terminal oxidant.
- Zhang, Ruipu,Qin, Yan,Zhang, Long,Luo, Sanzhong
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supporting information
p. 5629 - 5632
(2017/10/25)
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- Anti-bacterial, catalytic and docking behaviours of novel di/trimeric imidazolium salts
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Flexible di/trimeric substituted imidazolium salts are prepared under conventional/solvent free silica supported approaches. Solid supported approaches are superior than the conventional method like environment friendly, higher yield, shorter reaction time and easy workup procedure. We have studied the catalytic activities of our synthesized di/trimeric imidazolium salts for one-pot preparation of benzoxazole derivatives under conventional/Muffle furnace conditions. We have monitored the efficiency of recycled flexible di/trimeric imidazolium salts up to fourth cycles showed excellent responses. We have studied the MIC and MBC of our di/trimeric imidazolium salts against Gram positive/negative microorganisms under micro dilution method. Nitro substituted imidazolium salts showed excellent screening responses than the unsubstituted compounds. Computer assisted docking analysis is carried out for all our synthesized compounds. The host-guest interaction via hydrogen bonding between standard and our drug molecules against various human Gram positive and negative pathogens are compared. From the docking analysis, our drug molecules showed effective interaction against test pathogens.
- Ganapathi, Pandurangan,Ganesan, Kilivelu
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p. 452 - 464
(2017/03/24)
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- KMnO4/HOAc system promoted one-pot synthesis of benzoxazoles from o-aminophenols or oxidative cyclization of o-hydroxyarylidene anilines at room temperature
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1,3-Benzoxazoles via oxidative cyclization of corresponding o-hydroxyarylidene anilines was synthesized in the presence of KMnO4/HOAc system. This system also was applied for the one-pot synthesis of 1,3-benzoxazoles from o-amino phenols and aldehydes. The both protocols were processed at room temperature under solvent-free conditions with good to excellent yields.
- Mirjalili,Bamoniri,Bagheri
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p. 809 - 814
(2016/04/05)
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- Copper-catalyzed synthesis of benzoxazoles: Via tandem cyclization of 2-halophenols with amidines
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This work reports a simple, efficient and alternative synthetic route for the preparation of benzoxazoles via tandem cyclization of 2-halophenols with amidines. The developed methodology is free from ligands and uses inexpensive and easily available CuCl as a catalyst. This protocol avoids the use of any oxidant or inorganic acids. Various benzoxazole derivatives were synthesized in good to excellent yields. To the best of our knowledge, this is the first time that the synthesis of benzoxazoles from 2-halophenols with both aromatic and aliphatic amidines is reported. Owing to the simplicity of this protocol, the preparation of benzoxazoles could be achieved at a gram scale level.
- Tiwari, Abhishek R.,Bhanage, Bhalchandra M.
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p. 7920 - 7926
(2016/08/30)
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- S8-Mediated Cyclization of 2-Aminophenols/thiophenols with Arylmethyl Chloride: Approach to Benzoxazoles and Benzothiazoles
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A metal-free approach to benzazoles from arylmethyl chlorides and 2-mercaptan/2-hydroxyanilines using elemental sulfur as a traceless oxidizing agent has been developed. The reactions proceeded in good to excellent yields, exhibiting good functional groups tolerance and gram-scale ability. A key mechanistic investigation indicated that the key intermediate trisulfide 6, which was characterized by NMR, HRMS and crystal X-ray crystallography, was separated in the reaction prior to the formation of the product.
- Gan, Haifeng,Miao, Dazhuang,Pan, Qiang,Hu, Renhe,Li, Xiaotong,Han, Shiqing
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supporting information
p. 1770 - 1774
(2016/07/07)
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- Sustainable Synthesis of 2-Arylbenzoxazoles over a cobalt-based nanocomposite catalyst
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A new cobalt-based heterogeneous catalyst was prepared by adsorbing in situ produced nitrogen-ligated cobalt(II) acetate complexes on commercially available SiO2 and subsequent pyrolysis at 800 °C for 2 h under N2 atmosphere. By applying this catalyst under the O2 balloon, the aerobic oxidation of phenolic imines proceeded smoothly and gave various 2-arylbenzoxazoles in good yields. Meanwhile, on the basis of the experimental results, a plausible reaction pathway was described to elucidate the reaction mechanism.
- He, Jian,Lin, Fu,Yang, Xufang,Wang, Di,Tan, Xiaohua,Zhang, Shujun
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supporting information
p. 1093 - 1096
(2017/01/16)
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- A comparative study of the catalytic activity of Co- and CoFe2O4-NPs in C-N and C-O bond formation: synthesis of benzimidazoles and benzoxazoles from o-haloanilides
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Nanoparticles of cobalt ferrite (CoFe2O4-NPs) and pure cobalt (Co-NPs) were synthesized, and after characterization, their catalytic activities for dehalogenative intramolecular C-O and C-N bond formation reactions were investigated and compared. These inexpensive and efficient catalysts enabled creation of new methods for the synthesis of benzimidazoles and benzoxazoles in green media, with ligand-free and mild reaction conditions. All the reactions resulted in moderate to excellent yields under the optimized reaction conditions; however, the reactions using Co-NPs as the catalyst were completed in relatively shorter reaction times. Furthermore, analysis showed that the reusability of the two catalytic systems is approximately comparable.
- Hajipour, Abdol R.,Khorsandi, Zahra
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p. 10474 - 10481
(2016/12/07)
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