- Electrochemical oxidation-induced benzyl C–H carbonylation for the synthesis of aromatic α-diketones
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Electrochemical oxidation-induced direct carbonylation of benzyl C–H bond for the synthesis of aromatic α-diketones is described. In this process, tetrabutylammonium iodide (nBu4NI) not only acts as an electrolyte, but its iodine anion is oxidized to an iodine radical at the anode, acting as a hydrogen atom transfer agent. The iodine radical extracts the benzyl hydrogen atom and causes the carbonylation of the benzyl position, where O2 in the air is used as an oxygen source.
- Tan, Yu-Fang,Chen, Yuan,Li, Rui-Xue,Guan, Zhi,He, Yan-Hong
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- 1-butyl-3-methylimidazol-2-ylidene as an efficient catalyst for cross-coupling between aromatic aldehydes and N-aroylbenzotriazoles
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Cross-coupling of aromatic aldehydes with N-aroylbenzotriazoles in [Bmim]Br in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) provided an efficient procedure for the synthesis of 1,2-diarylethane-1,2-diones.
- Phungpis, Baramee,Hahnvajanawong, Viwat
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p. 651 - 657
(2021/02/27)
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- Synthesis of 1,2-diketones by mercury-catalyzed alkyne oxidation
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The first mercury-catalyzed synthesis of 1,2-diketones by alkyne oxidation has been developed. This inexpensive method extends the potential of mercury catalysis and allows the rapid construction of various 1,2-diketones and α-carbonyl amides in good yields with high functional group tolerance.
- Mei, Xiaochuan,Hu, Weican,Gao, Kexin,Gao, Haotian,Wang, Chaoyang,Qian, Guoying,Rong, Zhouting
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supporting information
p. 2661 - 2667
(2021/07/09)
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- Catalyst-Free and Transition-Metal-Free Approach to 1,2-Diketones via Aerobic Alkyne Oxidation
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A catalyst-free and transition-metal-free method for the synthesis of 1,2-diketones from aerobic alkyne oxidation was reported. The oxidation of various internal alkynes, especially more challenging aryl-alkyl acetylenes, proceeded smoothly with inexpensive, easily handled, and commercially available potassium persulfate and an ambient air balloon, achieving the corresponding 1,2-diketones with up to 85% yields. Meanwhile, mechanistic studies indicated a radical process, and the two oxygen atoms in the 1,2-diketons were most likely from persulfate salts and molecular oxygen, respectively, rather than water.
- Shen, Duyi,Wang, Hongyan,Zheng, Yanan,Zhu, Xinjing,Gong, Peiwei,Wang, Bin,You, Jinmao,Zhao, Yulei,Chao, Mianran
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p. 5354 - 5361
(2021/05/05)
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- Visible-Light-Induced Photocatalytic Oxidative Decarboxylation of Cinnamic Acids to 1,2-Diketones
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A concerted metallophotoredox catalysis has been realized for the efficient decarboxylative functionalization of α,β-unsaturated carboxylic acids with aryl iodides in the presence of perylene bisimide dye to afford 1,2-diketones.
- Chand, Shiv,Pandey, Anand Kumar,Singh, Rahul,Singh, Krishna Nand
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p. 6486 - 6493
(2021/05/06)
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- One-pot cascade synthesis of α-diketones from aldehydes and ketones in water by using a bifunctional iron nanocomposite catalyst
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A new methodology for the synthesis of α-diketones was reportedviaa one-pot cascade process from aldehydes and ketones catalyzed by a bifunctional iron nanocomposite using H2O2as a green oxidant in water. The one-pot strategy showed excellent catalytic stability, comprehensive suitability of substrates and important practical utility for directly synthesizing biologically active and medicinally valuable N-heterocyclesviaan intermittent process.
- Song, Tao,Zhou, Xin,Wang, Xiaoxue,Xiao, Jianliang,Yang, Yong
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supporting information
p. 1955 - 1959
(2021/03/26)
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- One-pot synthesis, structural analysis, and oxidation applications of a series of diaryltellurium dicarboxylates
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This paper presents a concise and efficient one-pot synthesis of a variety of functionalized diaryltellurium dicarboxylates. The method is based on a mild photosensitized oxygenation of cheap and readily available carboxylic acids. The molecular structures of the diaryltellurium dicarboxylates were determined unambiguously using single-crystal X-ray diffraction analysis. The thus obtained diaryltellurium dicarboxylates were used to study the oxidation of benzoin derivatives.
- Higashikawa, Go,Koguchi, Shinichi,Ohmura, Shiori,Shibuya, Yuga,Toyoda, Anna
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p. 32837 - 32840
(2021/12/07)
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- Dimethyl Sulfoxide as an Oxygen Atom Source Enabled Tandem Conversion of 2-Alkynyl Carbonyls to 1,2-Dicarbonyls
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A tandem transformation of 2-alkynyl carbonyl compounds by means of a CuBr2/I2/DMSO/water system is developed, enabling the fromation of various functionalized 1,2-dicarbonyl compounds, including 1,2-diketones, α-keto amides and α-keto ester. This Cu-promoted iodine-mediated tandem procedure employs DMSO as the oxygen atom source of the formed carbonyl group through iodonium ion formation, nucleophilic DMSO addition and C?C bond cleavage cascades. (Figure presented.).
- Hu, Ming,Li, Jin-Heng,Li, Yang,Lu, Yuan,Luo, Mu-Jia
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supporting information
(2020/05/01)
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- Copper/Iodine-Cocatalyzed C-C Cleavage of 1,3-Dicarbonyl Compounds Toward 1,2-Dicarbonyl Compounds
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A new, general oxidative route to transformations of 1,3-dicarbonyl compounds to 1,2-dicarbonyl compounds by merging copper and I2 catalysis is described. This method is applicable to broad 1,3-dicarbonyl compounds, including 1,3-diketones, 1,3-keto esters and 1,3-keto amides. Mechanistical studies show that the reaction is achieved via the C–C bond cleavage and CO release cascades.
- Chen, Li-Sha,Zhang, Lu-Bing,Tian, Yue,Li, Jin-Heng,Liu, Yong-Quan
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supporting information
p. 5523 - 5526
(2020/09/02)
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- Synthesis of unsymmetrical benzilsviapalladium-catalysed a-arylation-oxidation of 2-hydroxyacetophenones with aryl bromides
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A diverse set of unsymmetrically substituted benzils were facilely synthesised by a cross-coupling reaction between 2-hydroxyacetophenones and aryl bromides in the presence of a palladium catalyst. Experimental studies suggested a reaction mechanism involving a one-pot tandem palladium-catalysed a-arylation and oxidation, where aryl bromides play a dual role as mild oxidants as well as arylating agents.
- Matsuda, Takanori,Oyama, Souta
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supporting information
p. 3679 - 3683
(2020/06/03)
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- Synthetic method and application of diphenylglyoxal compound
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The invention provides a preparation method of a synthetic diphenylglyoxal compound. A methylbenzene compound is oxidized by oxygen under the co-catalysis action of cuprous bromide, sodium nitrite, DDQ and protonic acid, and the diphenylglyoxal compound is prepared by a one-step method. Through suitable selectivity and collaboration of a catalyst and a reaction condition, a target product with high yield is realized, the efficiency is high in the preparation process, the cost is low, very outstanding technical significance and application value are achieved in the field of medical intermediatesynthesis, and market prospects are wide.
- -
-
Paragraph 0017-0019
(2019/11/20)
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- Preparation method of bibenzoyl compound and application
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The invention provides a preparation method for synthesizing dibenzoyl compounds. Under the co catalysis of cuprous bromide, sodium nitrite, DDQ and protonic acid, a benzyl alcohol compound is oxidized by oxygen, and a bibenzoyl compound is obtained by a one-step method. Through the appropriate selection and coordination of the catalyst, reaction conditions and the like, target products with highyield are obtained, and in the preparation process, the efficiency is good, and the cost is low; and the technical significance and application value in the field of pharmaceutical intermediates synthesis are significant, and the market prospect is wide.
- -
-
Paragraph 0018-0020
(2019/11/20)
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- ICl/AgNO3 Co-catalyzed radical oxidation of diaryl- A nd alkylarylalkynes into 1,2-diketones
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A novel ICl/AgNO3 co-catalyzed radical oxidation of diaryl- A nd alkylarylalkynes into 1,2-diketones is reported. The reaction proceeded smoothly under mild conditions and generated 1,2-diketones in moderate to good yields with a good tolerance of functional groups. Furthermore, the obtained C4-(1,2-diketoaryl)isoxazoles could react smoothly with 1,2-diaminobenzene to form C4-(3-arylquinoxalin-2-yl)isoxazoles. At last, a new one-pot strategy for the synthesis of quinoxalines from 1,2-diphenylethynes and 1,2-diaminobenzene is also reported.
- Yang, Wen,Chen, Yu,Yao, Yongqi,Yang, Xin,Lin, Qifu,Yang, Dingqiao
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p. 11080 - 11090
(2019/09/09)
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- Sequentially Pd/Cu-Catalyzed Alkynylation-Oxidation Synthesis of 1,2-Diketones and Consecutive One-Pot Generation of Quinoxalines
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We report a simple and efficient one-pot synthesis of 1,2-diketones by concatenation of two Pd/Cu-catalyzed processes: Pd0/CuI-catalyzed Sonogashira coupling of terminal alkynes with aryl (pseudo)halides furnishes internal alkynes, which are directly transformed by PdII/CuII-catalyzed Wacker-type oxidation with DMSO and oxygen as dual oxidants to furnish 1,2-diketones. With this efficient, catalyst economical process, various aryl iodides and triflates are efficiently transformed in high yields into symmetrically and unsymmetrically substituted 1,2-diketones with various functional groups. This process can be readily extended to a consecutive one-pot synthesis of quinoxalines in a diversity-oriented fashion.
- Niesobski, Patrik,Martínez, Ivette Santana,Kustosz, Sebastian,Müller, Thomas J. J.
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supporting information
p. 5214 - 5218
(2019/07/31)
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- Ring Closing Metathesis Approach for the Synthesis of o-Terphenyl Derivatives
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A linear synthesis of o-terphenyl derivatives has been delineated using ring closing metathesis (RCM) as the key step. In this approach, benzil derivatives upon allyl Grignard addition provides diphenyl-1,2-diallyl dihydroxy derivatives which undergo ring closing metathesis to afford tetrahydro terphenyl derivatives. Aromatization-driven dehydration then leads to a diverse set of electron rich and electron deficient o-terphenyls. Furthermore, oxidative coupling of electron rich o-terphenyls provides the corresponding triphenylene derivatives.
- Karmakar, Shilpi,Mandal, Tirtha,Dash, Jyotirmayee
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p. 5916 - 5924
(2019/08/21)
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- Method for synthesizing benzil derivatives
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The invention discloses a method for synthesizing benzil derivatives. The method comprises the steps that a diphenyl acetylene compound, halogenated ammonium salt or iodine chloride and a sulfur source serve as reactants, the reactants react in a solvent for a period of time, purification is conducted, and then the benzil derivatives are obtained. According to the method, a metal catalyst and toxic iodine are not used, the applied reactants are low in price, poisonless and tasteless, the operation method is simple, the yield is high, aftertreatment is easy, and the method is suitable for industrial production.
- -
-
Paragraph 0079; 0080; 0081; 0082
(2019/01/23)
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- Substituent Effect in the Synthesis of α,α-Dibromoketones, 1,2-Dibromalkenes, and 1,2-Diketones from the Reaction of Alkynes and Dibromoisocyanuric Acid
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Internal alkynes reacted with dibromoisocyanuric acid/H2O to afford α,α-dibromoketone and 1,2-diketone derivatives. Diarylalkynes with activating groups provided 1,2-diketone derivatives as the major products, whereas diarylalkynes with a non-activating group or alkylarylalkynes gave α,α-dibromoketone derivatives as the major products. In addition, diarylalkynes with deactivating groups provided 1,2-dibromoalkenes. The reaction was conducted at room temperature and showed good yields in most cases. Reaction pathways have been proposed on the basis of experimental observations and density functional theory (DFT) calculations. (Figure presented.).
- Cho, Eunjeong,Jayaraman, Aravindan,Lee, Junseong,Ko, Kyoung Chul,Lee, Sunwoo
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p. 1846 - 1858
(2019/03/07)
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- B2pin2-mediated copper-catalyzed oxidation of alkynes into 1,2-diketones using molecular oxygen
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An intriguing aerobic oxidation of alkynes through copper catalysis is described, in which bis(pinacolato)diboron (B2pin2) played a dominant intermediary role in the formation 1,2-diketones. This novel protocol, which can be performed at room temperature, is versatile for various substituted alkynes, including diarylalkynes and arylalkylalkynes. The mechanism of this reaction was preliminarily investigated by control experiments.
- Zhai, Yadong,Su, Zhenni,Jiang, Hao,Rong, Jing,Qiu, Xianfan,Tao, Chuanzhou
-
supporting information
p. 843 - 846
(2019/02/19)
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- Electrochemical synthesis of 1,2-diketones from alkynes under transition-metal-catalyst-free conditions
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We report an electrochemical protocol for the direct oxidation of internal alkynes in air to provide 1,2-diketones. A variety of functional groups and heterocycle-containing substrates can be tolerated well under mild conditions.
- Zhou, Jie,Tao, Xiang-Zhang,Dai, Jian-Jun,Li, Chen-Guang,Xu, Jun,Xu, Hong-Mei,Xu, Hua-Jian
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supporting information
p. 9208 - 9211
(2019/08/07)
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- Synthesis, anti-proliferative evaluation, and molecular docking studies of 3-(Alkylthio)-5,6-diaryl-1,2,4-triazines as tubulin polymerization inhibitors
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Background: The role of microtubules in cell division and signaling, intercellular transport, and mitosis has been well known. Hence, they have been targeted for several anti-cancer drugs. Methods: A series of 3-(alkylthio)-5,6-diphenyl-1,2,4-triazines were prepared and evaluated for their cytotoxic activities in vitro against three human cancer cell lines; human colon carcinoma cells HT-29, human breast adenocarcinoma cell line MCF-7, human Caucasian gastric adenocarcinoma cell line AGS as well as fibroblast cell line NIH-3T3 by MTT assay. Docking simulation was performed to insert these compounds into the crystal structure of tubulin at the colchicine binding site to determine a probable binding model. Compound 5d as the most active compound was selected for studying of microtubule disruption. Results: Compound 5d showed potent cytotoxic activity against all cell lines. The molecular modeling study revealed that some derivatives of triazine strongly bind to colchicine binding site. The tubulin polymerization assay kit showed that the cytotoxic activity of 5d may be related to inhibition of tubulin polymerization. Conclusion: The cytotoxicity and molecular modeling study of the synthesized compounds with their inhibition activity in tubulin polymerization demonstrate the potential of triazine derivatives for development of new anti-cancer agents.
- Saravani, Farhad,Moghadam, Ebrahim Saeedian,Salehabadi, Hafezeh,Ostad, Seyednasser,Hamedani, Morteza Pirali,Amanlou, Massoud,Faramarzi, Mohammad Ali,Amini, Mohsen
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p. 1194 - 1201
(2019/11/22)
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- Silver-Catalyzed Decarboxylative Couplings of Acids and Anhydrides: An Entry to 1,2-Diketones and Aryl-Substituted Ethanes
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Silver-catalyzed oxidative decarboxylative couplings of carboxylic acids and anhydrides to produce 1,2-diketones and substituted ethanes were developed. This reaction allows the generation of acyl or alkyl radicals by decarboxylation of the corresponding α-keto acids, alkyl acids and anhydrides, which are sequentially coupled to efficiently construct a new C?C bond. This reaction represents a carboxylic acid decarboxylative alternative that employs a radical termination strategy. (Figure presented.).
- Zou, Hua-Xu,Li, Yang,Yang, Yuan,Li, Jin-Heng,Xiang, Jiannan
-
supporting information
p. 1439 - 1443
(2018/02/26)
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- Two-Step One-Pot Synthesis of Unsymmetrical (Hetero)Aryl 1,2-Diketones by Addition-Oxygenation of Potassium Aryltrifluoroborates to (Hetero)Arylacetonitriles
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An efficient one-pot two-step procedure for the synthesis of unsymmetrical (hetero)aryl 1,2-diketones has been developed. The reaction proceeds through a palladium-catalyzed nucleophilic addition of potassium aryltrifluoroborates to aliphatic nitriles followed by a copper-catalyzed aerobic benzylic C–H oxygenation using molecular oxygen as a green oxidant. This represents the first example of the direct synthesis of unsymmetrical diaryl 1,2-diketones from arylacetonitriles. This method utilizes inexpensive, stable, nontoxic, and readily available starting materials, is highly effective in the presence of both electron-rich and electron-poor nitriles and aryltrifluoroborates, and tolerates a wide variety of functional groups. The synthetic utility of this transformation was shown by increasing the scale of the reaction and by carrying out the one-pot protocol for the preparation of quinoxaline and benzimidazole derivatives. A plausible reaction mechanism has also been proposed.
- Kumar, Yogesh,Jaiswal, Yogesh,Kumar, Amit
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p. 494 - 505
(2018/02/09)
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- NH4I/EtOCS2K promoted synthesis of substituted benzils from diphenylacetylene derivatives
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A facile protocol is described for the synthesis of benzil derivatives from readily accessible diarylacetylene derivatives using the NH4I/EtOCS2K system. This novel protocol results in excellent chemoselectivity and provided good to excellent yields. A control experiment indicated that the reaction proceeds via NH4I promoted EtOCS2K dimerization to give the corresponding dixanthogen and subsequent dixanthogen assisted oxidation.
- Jiang, Shaohua,Li, Yibiao,Luo, Xianglin,Huang, Guoling,Shao, Yan,Li, Dongli,Li, Bin
-
supporting information
p. 3249 - 3252
(2018/07/21)
-
- Synthesis of a new class of cationic Pd(II) complexes with 1,2,3-triazol-5-ylidene ligand and their catalytic application in the conversion of internal alkynes to 1,2-diketones
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A new class of cationic Pd(II) complexes of the type [Pd(Tz)(Cl)(bipy)]+Cl? and [Pd (Tz)(Cl)(phen)]+Cl? (Tz = 1,4-diaryl-3-methyl-1,2,3-triazol-5-ylidene, bipy = 2,2′-bipyridine and phen = 1,10-phenanthroline) with various wing tip groups were synthesized from the corresponding 1,2,3-triazolium iodide via the corresponding chloro bridged dinuclear complexes [(Tz)(Cl)Pd(μ-Cl)2Pd(Cl)(Tz)]. The synthesized cationic complexes were screened for their catalytic activity of hydration of alkynes and found to be excellent towards the selective conversion of internal alkynes to the corresponding 1,2-diketones in good yields. A plausible mechanism was proposed for this conversion.
- Shaik, Jeelani Basha,Ramkumar, Venkatachalam,Sankararaman, Sethuraman
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supporting information
p. 1 - 8
(2018/02/19)
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- Magnetic magnetite nanoparticals catalyzed selective oxidation of Α-hydroxy ketones with air and one-pot synthesis of benzilic acid and phenytoin derivatives
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A clean and efficient protocol for selective oxidation of α-hydroxy ketones using magnetic magnetite nanoparticals (Fe3O4·MNPs) as catalyst with air as green oxidant has been developed. Application of Fe3O4·MNPs was also proved to be successful in one-pot synthesis of benzilic acid and phenytoin derivatives. The facile one-pot procedure enhanced the production efficiency, shortened the reaction time and minimized the chemical waste. Notably, the catalyst can be reused at least for five times without any appreciable loss of its activity.
- Li, Xiaona,Xia, Dandan,Wen, Zhiyong,Gong, Bowen,Sun, Maolin,Wu, Yue,Zhang, Jie,Sun, Jun,Wu, Yang,Bao, Kai,Zhang, Weige
-
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- A manganese Schiff base complex immobilized on copper–ferrite magnetic nanoparticles as an efficient and recyclable nanocatalyst for selective oxidation of alcohols
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A magnetically recoverable nanocatalyst was synthesized by covalent binding of a Schiff base ligand, namely N,N′-bis(Salicylidene)-1,3-diaminopropane-2-ol (H2salpn), onto the surface of silica-coated magnetic CuFe2O4 nanoparticles, followed by complexation with MnCl2. The resulting core–shell nanoparticles were characterized by spectroscopic and microscopic methods, including FTIR, XRD, VSM, TGA elemental analysis, TEM, and SEM. The Mn content was determined by ICP analysis. The nanoparticles were investigated as a catalyst for the selective oxidation of alcohols to the corresponding carbonyl compounds with tertiary-butyl hydrogen peroxide. The catalyst can be magnetically separated for reuse, with no noticeable loss of activity in subsequent reaction cycles. FTIR, VSM, and leaching experiments after three successive cycles confirmed that the catalyst was strongly anchored to the magnetic nanoparticles. A suitable mechanism for the reaction is proposed.
- Tavakoli Hafshejani, Mahmood,Saeednia, Samira,Hatefi Ardakani, Mehdi,Pakdin Parizi, Zahra
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p. 579 - 589
(2018/05/15)
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- Copper-catalyzed TEMPO oxidative cleavage of 1,3-diketones and β-keto esters for the synthesis of 1,2-diketones and α-keto esters
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A copper-catalyzed efficient and practical method has been developed for the synthesis of 1,2-diketones and α-keto esters. TEMPO was used as a radical initiator and scavenger, oxidizing the cleavage of α-methylene of 1,3-diketones and β-keto esters to form 1,2-diketones and α-keto esters. This method provided a general way for the formation of 1,2-dicarbonyl compounds.
- Zhou, Peng-Jun,Li, Cheng-Kun,Zhou, Shao-Fang,Shoberu, Adedamola,Zou, Jian-Ping
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p. 2629 - 2637
(2017/04/03)
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- NaBrO3/bmim[HSO4]: a versatile system for the selective oxidation of 1,2-diols, α-hydroxyketones, and alcohols
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Abstract: Sodium bromate with bmim[HSO4] has been found to be an excellent oxidizing agent in aqueous medium. NaBrO3:bmim[HSO4] oxidized 1,2-diols, α-hydroxyketones, and alcohols to the corresponding carbonyl compounds in excellent yields. This method offers advantages such as low cost reagents, aqueous reaction conditions, moderate temperatures and short reaction times and hence environmentally benign reaction. Moreover, the ionic liquid bmim[HSO4] could be recycled for at least three times without loss of significant activity. Graphical abstract: [Figure not available: see fulltext.]
- Khurana, Jitender M.,Lumb, Anshika,Chaudhary, Ankita
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p. 381 - 386
(2017/02/10)
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- CO2-assisted synthesis of non-symmetric α-diketones directly from aldehydes: Via C-C bond formation
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CO2-assisted various symmetric and non-symmetric α-diketones have been synthesized directly from the corresponding aldehydes using transition metal-free catalysts. This method can even be applied to synthesize pharmaceuticals directly from aldehydes. The crucial role of CO2 has been investigated in detail and the mechanism is proposed on the basis of experiments and DFT calculations.
- Hirapara, Pradipbhai,Riemer, Daniel,Hazra, Nabanita,Gajera, Jignesh,Finger, Markus,Das, Shoubhik
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supporting information
p. 5356 - 5360
(2017/11/22)
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- Synthesis of smart bimetallic nano-Cu/Ag@SiO2 for clean oxidation of alcohols
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Here, we have demonstrated the synthesis and characterization of silica supported bimetallic copper/silver nanoparticles (Cu/Ag@SiO2 NPs) and their application in the clean oxidation of benzoins/benzyl alcohols in the presence of tert-butyl hydroperoxide as a mild oxidant. All the reactions were very fast (4 h) and high yielding (95-99%), and the Cu/Ag@SiO2 NPs were very stable under the reaction conditions. The catalyst was recovered simply by filtration and reused eight times without loss of its catalytic performance.
- Saha, Arijit,Payra, Soumen,Banerjee, Subhash
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p. 13377 - 13381
(2017/11/27)
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- Reaction control in heterogeneous catalysis using montmorillonite: Switching between acid-catalysed and red-ox processes
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The use of montmorillonite, modified with a super-acid (CF3SO3H), in the presence of hydroquinone as a radical scavenger and under a nitrogen atmosphere, induced the formation of tetrasubstituted furans as the major product from benzoins. In the absence of a radical scavenger, the only products obtained were 1,2-diketones.
- Morales-Serna, José Antonio,Frontana-Uribe, Bernardo A.,Olguín, Rosario,Gómez-Vidales, Virginia,Lomas-Romero, Leticia,Garcia-Ríos, Erendira,Gavi?o, Ruben,Cárdenas, Jorge
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p. 42613 - 42617
(2016/05/19)
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- Preparation method of 1,2-diketone derivative
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The invention discloses a preparation method of a 1,2-diketone derivative. The method comprises the step of enabling a raw material 1,3-diketone derivative to react with a cheap and easily obtained industrial product 2,2,6,6-tetramethyl-1-piperidinyloxy under the catalysis of copper so as to obtain the product 1,2-diketone derivative. According to the preparation method, the 1,3-diketone derivative is used as an initiator, and the raw material is easy to obtain and wide in variety; by utilizing the preparation method, the obtained product types are varied, can be directly used, and can be used for other further reactions; in addition, the reagent dosage in the reaction is less, the pollution is reduced, and the production cost is lowered; moreover the reaction conditions are mild, the reaction operation and the after-treatment process are simple, the reaction time is short, the yield is high, and the preparation method is suitable for industrial production.
- -
-
Paragraph 0023
(2016/10/08)
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- Highly efficient asymmetric hydrogenation of cyano-substituted acrylate esters for synthesis of chiral γ-lactams and amino acids
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A highly efficient and enantioselective synthesis of γ-lactams and γ-amino acids by Rh-catalyzed asymmetric hydrogenation has been developed. Using the Rh-(S,S)-f-spiroPhos complex, under mild conditions a wide range of 3-cyano acrylate esters including both E and Z-isomers and β-cyano-α-aryl-α,β-unsaturated ketones were first hydrogenated with excellent enantioselectivities (up to 98% ee) and high turnover numbers (TON up to 10 000).
- Kong, Duanyang,Li, Meina,Wang, Rui,Zi, Guofu,Hou, Guohua
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p. 1216 - 1220
(2016/02/03)
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- Synthesis and characterization of a magnetically recoverable molybdenum(VI) nanocatalyst for eco-friendly oxidation of alcohols
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A catalyst based on immobilization of a molybdenum(VI) Schiff base complex on γ-Fe2O3 magnetic nanoparticles has been synthesized and characterized. This catalyst was employed for the selective oxidation of alcohols to the corresponding carbonyl compounds in EtOH/H2O2. The catalyst can be easily separated from the reaction mixture by decantation using an external magnet and reused efficiently in five subsequent reaction cycles without any significant decrease in activity or selectivity.
- Saeednia,Ardakani, M. Hatefi,Parizi, Z. Pakdin,Hafshejani, M. Tavakoli
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p. 767 - 774
(2016/09/13)
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- Dendrimer-like core cross-linked micelle stabilized ultra-small gold nanoclusters as a robust catalyst for aerobic oxidation of α-hydroxy ketones in water
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As one of the most general and promising stabilizers, dendrimers have been widely used to prepare ultra-small gold nanoclusters. However, the complex synthesis of dendrimers hinders the further application of protected nanoclusters. Here we report a facile strategy to prepare an alternative material via core cross-linking of self-assembled micelles. The resulting dendrimer-like core cross-linked micelles (DCCMs) retain the main characteristics of dendrimers and avoid complex chemical synthesis. As expected, the DCCMs could easily encapsulate gold nanoparticles within their cores. The ultra-small clusters of Au5 were prepared without the participation of external reductants. Importantly, the DCCM stabilized noble gold clusters furnish excellent catalytic activity and perfect reusability for aerobic oxidation of α-hydroxy ketones in water. Only in open air the oxidation could be repeated up to 48 times with negligible turn-over frequency change. The total turnover number (TON) of the reaction reached unexpectedly >48 000, the highest TON for metal catalysed oxidation of hydroxy ketones so far. The further mechanism study hints that the carboxylic group of substrates might be involved in the catalytic process. The simple catalyst preparation, the environmentally benign reaction conditions, and the excellent catalytic performance and durability make the novel DCCM protected gold nanocluster a green catalyst.
- Yu, Yangyang,Lin, Chenlu,Li, Bing,Zhao, Pengxiang,Zhang, Shiyong
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p. 3647 - 3655
(2016/07/06)
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- PTSA-catalyzed one-pot synthesis of quinoxalines using DMSO as the oxidant
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An efficient p-toluene sulfonic acid–catalyzed, one-pot, two-step oxidative system for cyclization of o-diaminobenzene with 1,2-diaryl-2-hydroxyethanone to quinoxalines was described. A nontoxic, readily available oxidant, dimethylsulfoxide (DMSO), was applied in this process. A broad range of substrates was applied to this method, and target compounds were obtained with good yields.
- Zhang, Zeyuan,Xie, Caixia,Feng, Lei,Ma, Chen
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p. 1507 - 1518
(2016/09/28)
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- Copper-catalyzed base-accelerated direct oxidation of C-H bond to synthesize benzils, isatins, and quinoxalines with molecular oxygen as terminal oxidant
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We describe herein an efficient and general copper (II)-catalyzed base-accelerated oxidation of the C-H bond to synthesize benzils and isatins. With similar oxidation system an efficient one-pot procedure for the synthesis of quinoxaline derivatives was realized. The two protocols feature using molecular oxygen as terminal oxidant, low catalyst loading, wide substrate scope, and high functional-group tolerance.
- Yu, Jing-Wen,Mao, Shuai,Wang, Yong-Qiang
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p. 1575 - 1580
(2015/03/14)
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- Organic inorganic hybrid cobalt phthalocyanine/polyaniline as efficient catalyst for aerobic oxidation of alcohols in liquid phase
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Organic inorganic hybrid catalyst synthesized by doping of cobalt phthalocyanine (CoPc) on polyaniline support (CoPc/PANI) exhibited higher activity for the oxidation of various alcohols to the corresponding carbonyl compounds in high to excellent yield using molecular oxygen as oxidant and isobutyraldehyde as a sacrificial agent. Notably, the synthesized catalyst was found to be truly heterogeneous in nature and could be easily recovered, recycled for several recycling runs without loss of catalytic activity.
- Panwar, Vineeta,Kumar, Pawan,Ray, Siddharth S.,Jain, Suman L.
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p. 3948 - 3953
(2015/06/08)
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- An efficient iodine-DMSO catalyzed synthesis of quinoxaline derivatives
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An efficient iodine-DMSO catalyzed system for the synthesis of quinoxaline derivatives was developed. The construction of this quinoxaline system went through a one-pot oxidation/cyclization process. The reaction afforded a variety of products in good to excellent yields. This methodology has potential applications in the synthesis of biologically and medicinally relevant compounds.
- Xie, Caixia,Zhang, Zeyuan,Yang, Bingchuan,Song, Gaolei,Gao, He,Wen, Leilin,Ma, Chen
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p. 1831 - 1837
(2015/03/04)
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- Copper-catalyzed direct synthesis of diaryl 1,2-diketones from Aryl iodides and propiolic acids
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Benzil derivatives such as diaryl 1,2-diketones are synthesized via the direct decarboxylative coupling reaction of aryl propiolic acids and their oxidation. The optimized conditions are that the reaction of aryl propiolic acids and aryl iodides is conducted at 140°C for 6 h in the presence of 10 mol % CuI/Cu(OTf)2 and Cs2CO3, after which HI (aq) is added and further reacted. The method shows good functional group tolerance toward ester, aldehyde, cyano, and nitro groups. In addition, symmetrical diaryl 1,2-diketones are obtained from aryl iodides and propiolic acid in the presence of palladium and copper catalysts.
- Min, Hongkeun,Palani, Thiruvengadam,Park, Kyungho,Hwang, Jinil,Lee, Sunwoo
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p. 6279 - 6285
(2014/07/21)
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- Stoichiometric reactions of acylnickel(II) complexes with electrophiles and the catalytic synthesis of ketones
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Acylnickel(II) complexes feature prominently in cross-electrophile coupling (XEC) reactions that form ketones, yet their reactivity has not been systematically investigated. We present here our studies on the reactivity of acylnickel(II) complexes with a series of carbon electrophiles. Bromobenzene, α-chloroethylbenzene, bromooctane, and iodooctane were reacted with (dtbbpy)NiII(C(O)C5H11)(Br) (1b) and (dtbbpy)NiII(C(O)tolyl)(Br) (1c) to form a variety of organic products. While reactions with bromobenzene formed complex mixtures of ketones, reactions with α-chloroethylbenzene were highly selective for the cross-ketone product. Reactions with iodooctane and bromooctane also produced the cross-ketone product, but in intermediate yield and selectivity. In most cases the presence or absence of a chemical reductant (zinc) had only a small effect on the selectivity of the reaction. The coupling of 1c with iodooctane (60% yield) was translated into a catalytic reaction, the carbonylative coupling of bromoarenes with primary bromoalkanes (six examples, 60% average yield).
- Wotal, Alexander C.,Ribson, Ryan D.,Weix, Daniel J.
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supporting information
p. 5874 - 5881
(2015/01/09)
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- Copper-mediated aerobic oxidative cleavage of α,β-unsaturated ketones to 1,2-diketones
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The copper-mediated aerobic oxidative cleavage of α,β- unsaturated ketones to synthesize 1,2-diketones by using potassium acetate as a catalyst and sodium iodide as a promoter in acetic acid is described. The protocol has the advantages of using inexpensive and non-toxic raw materials, high yield and simple work-up procedure. the Partner Organisations 2014.
- Li, Zheng,Yin, Junjun,Wen, Gong,Li, Tianpeng,Shen, Xiaoli
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p. 32298 - 32302
(2014/08/18)
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- Unexpected transformation of aldehydes into benzoins with Copper(I)/Samarium
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The reductive coupling of aldehydes to afford pinacolic alcohols using all kinds of reducing agents involving samarium is well known. In this report, however, treatment of aromatic aldehydes with Cu(I)/Sm system produces benoins and/or benzils in good yields. A possible mechanism is proposed where Cu(I) not only activates the Sm metal but also promotes the dehydrogenation of the intermediates, during which a Cu(III) species may be involved. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]
- Liu, Yongjun,Wang, Hui,Fu, Yulong,Qi, Yan,Yang, Kuiwei
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p. 259 - 266
(2013/12/04)
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- Copper-catalyzed aerobic oxidative C-C bond cleavage of 1,3-diaryldiketones to synthesize 1,2-diketones
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An aerobic oxidative C-C bond cleavage of 1,3-diaryldiketones for the synthesis of 1,2-diketones by using O2 as the oxidant has been developed. Control experiments illustrate that the copper catalyst not only assist the aerobic oxidative process of 1,3-diketones, but also catalyze the 1,2-Wagner-Meerwein-type rearrangement process. Georg Thieme Verlag Stuttgart. New York.
- Zhang, Chun,Wang, Xiaoyang,Jiao, Ning
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supporting information
p. 1458 - 1460
(2014/06/23)
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- Lanthanum triflate-catalyzed rapid oxidation of secondary alcohols using hydrogen peroxide urea adduct (UHP) in ionic liquid
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A convenient and efficient protocol for the oxidation of secondary hydroxyl group to ketone using hydrogen peroxide-urea adduct and catalytic (CF 3SO3)3La in ionic liquid has been developed. A number of 1,2-diols, -hydroxyketones, and other aromatic and aliphatic secondary alcohols have been successfully oxidized to the corresponding ketones using this protocol in good yields and short reaction times. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]
- Saluja, Pooja,Magoo, Devanshi,Khurana, Jitender M.
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supporting information
p. 800 - 806
(2014/03/21)
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- Synthesis of ferrocene derivatives with planar chirality via palladium-catalyzed enantioselective C-H bond activation
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The first catalytic and enantioselective C-H direct acylation of ferrocene derivatives has been developed. A series of 2-acyl-1-dimethylaminomethylferrocenes with planar chirality were provided under highly efficient and concise one-pot conditions with up to 85% yield and 98% ee. The products obtained could be easily converted to various chiral ligands via diverse transformations.
- Pi, Chao,Cui, Xiuling,Liu, Xiuyan,Guo, Mengxing,Zhang, Hanyu,Wu, Yangjie
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supporting information
p. 5164 - 5167
(2014/12/11)
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- Selective oxygenation of alkynes: A direct approach to diketones and vinyl acetate
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Arylalkynes can be converted into α-diketones with the use of a copper catalyst, and also be transformed into vinyl acetates under metal-free conditions, both in the presence of PhI(OAc)2 as an oxidant at room temperature. A series of substituted α-diketones were prepared in moderate to good yields. A variety of vinyl halides could be regio- and stereo-selectively synthesized under mild conditions, and I, Br and Cl could be all easily embedded into the alkynes. This journal is
- Xia, Xiao-Feng,Gu, Zhen,Liu, Wentao,Wang, Ningning,Wang, Haijun,Xia, Yongmei,Gao, Haiyan,Liu, Xiang
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supporting information
p. 9909 - 9913
(2015/01/09)
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- Synthesis and anticancer activity of 2,4,5-triaryl imidazole derivatives
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This study describes the synthesis of four 2,4,5-triarylimidazole derivatives and their anticancer activities. The target compounds were prepared from the reaction of benzaldehyde and benzoin derivatives in presence of ammonium acetate and ammonium vanadate. All the synthesized compounds were screened for anticancer activities against T47D and MDA-MB231 cell lines using the MTT assay. However, our obtained results indicated a significant difference between colchicines cytotoxicity and their homologs on treated MDA-MB231 and T47D cells; one compound (4a) showed a significant IC50 on MDA-MB231 cells in cell culture assay.
- Elahian, Fatemeh,Akbari, Morteza,Ghasemi, Maryam,Behtooee, Neda,Taheri, Mohaddeseh,Amini, Mohsen
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p. 840 - 843
(2014/07/21)
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- N-Heterocyclic carbene-catalyzed double acylation of enones with benzils
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Thiazolium carbene-catalyzed reaction of aromatic 1,2-diketones with enones in aprotic solvents gave double acylation products in good yields, whereas hydroacylation products formed by Stetter reaction were not detected at all. These results suggested the generation of aroyloxyenamine species from the 1,2-diketones instead of hydroxyenamines (Breslow intermediates). This journal is
- Takaki, Ken,Ohno, Akira,Hino, Makoto,Shitaoka, Takashi,Komeyama, Kimihiro,Yoshida, Hiroto
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p. 12285 - 12288
(2014/12/11)
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- Co3O4-decorated carbon nanotubes as a novel efficient catalyst in the selective oxidation of benzoins
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An efficient and facile air oxidation of benzoins in the presence of the heterogeneous catalyst, Co3O4-CNTs nanocomposite, has been developed. It thus constitutes a very simple, clean, economical and selective method for the aerobic preparation of benzils from the corresponding benzoins. The catalyst can be re-used a number of times without losing its catalytic activity to a greater extent.
- Safari, Javad,Mansouri Kafroudi, Zahra,Zarnegar, Zohre
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p. 958 - 963
(2014/08/18)
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