- New processes for the synthesis of 2,6-dichloro-3- methylaniline-Ph-UL-14C and methyl 6-chloroanthranilate-Ph-UL-14C
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Two new processes were developed for the synthesis of 2,6-dichloro-3-methylaniline-Ph-UL-14C (1), a key intermediate in the synthesis of a DowElanco experimental product presently being considered for commercialization. Both processes afford product in much higher yields than that previously reported in the literature. One of the processes was subsequenly applied to the synthesis of methyl 6-chloroanthranilate-Ph-14C (12), used as an intermediate for a second potential product.
- McKendry,Stanga
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- Cationic Iridium-Catalyzed Asymmetric Decarbonylative Aryl Addition of Aromatic Aldehydes to Bicyclic Alkenes
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We report an unprecedented catalytic protocol for the enantioselective decarbonylative transformation of aryl aldehydes. In this process, the decarbonylation of aldehydes catalyzed by chiral iridium complexes enabled the formation of asymmetric C?C bonds
- Nonami, Reina,Morimoto, Yusei,Kanemoto, Kazuya,Yamamoto, Yasunori,Shirai, Tomohiko
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- Efficient nitriding reagent and application thereof
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The invention discloses an efficient nitriding reagent and application thereof, wherein the nitriding reagent comprises nitrogen oxide, an active agent, a reducing agent and an organic solvent. By applying the nitriding reagent, nitrogen-containing compounds such as amide, nitrile and the like can be produced, and the method is simple in condition, low in waste discharge amount and simple in reaction equipment.
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Paragraph 0161-0163
(2021/03/31)
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- Chemoselective reduction of nitroarenes, N-acetylation of arylamines, and one-pot reductive acetylation of nitroarenes using carbon-supported palladium catalytic system in water
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Developing and/or modifying fundamental chemical reactions using chemical industry-favorite heterogeneous recoverable catalytic systems in the water solvent is very important. In this paper, we developed convenient, green, and efficient approaches for the chemoselective reduction of nitroarenes, N-acetylation of arylamines, and one-pot reductive acetylation of nitroarenes in the presence of the recoverable heterogeneous carbon-supported palladium (Pd/C) catalytic system in water. The utilize of the simple, effective, and recoverable catalyst and also using of water as an entirely green solvent along with relatively short reaction times and good-to-excellent yields of the desired products are some of the noticeable features of the presented synthetic protocols. Graphic abstract: [Figure not available: see fulltext.].
- Zeynizadeh, Behzad,Mohammad Aminzadeh, Farkhondeh,Mousavi, Hossein
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p. 3289 - 3312
(2021/05/11)
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- Discovery of novel quinoline-based analogues of combretastatin A-4 as tubulin polymerisation inhibitors with apoptosis inducing activity and potent anticancer effect
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A new series of quinoline derivatives of combretastatin A-4 have been designed, synthesised and demonstrated as tubulin polymerisation inhibitors. These novel compounds showed significant antiproliferative activities, among them, 12c exhibited the most potent inhibitory activity against different cancer cell lines (MCF-7, HL-60, HCT-116 and HeLa) with IC50 ranging from 0.010 to 0.042 μM, and with selectivity profile against MCF-10A non-cancer cells. Further mechanistic studies suggest that 12c can inhibit tubulin polymerisation and cell migration, leading to G2/M phase arrest. Besides, 12c induces apoptosis via a mitochondrial-dependant apoptosis pathway and caused reactive oxygen stress generation in MCF-7 cells. These results provide guidance for further rational development of potent tubulin polymerisation inhibitors for the treatment of cancer.Highlights A novel series of quinoline derivatives of combretastatin A-4 have been designed and synthesised. Compound 12c showed significant antiproliferative activities against different cancer cell lines. Compound 12c effectively inhibited tubulin polymerisation and competed with [3H] colchicine in binding to tubulin. Compound 12c arrested the cell cycle at G2/M phase, effectively inducing apoptosis and inhibition of cell migration.
- Ibrahim, Tarek S.,Hawwas, Mohamed M.,Malebari, Azizah M.,Taher, Ehab S.,Omar, Abdelsattar M.,Neamatallah, Thikryat,Abdel-Samii, Zakaria K.,Safo, Martin K.,Elshaier, Yaseen A. M. M.
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p. 802 - 818
(2021/03/29)
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- Novel hybrid conjugates with dual estrogen receptor α degradation and histone deacetylase inhibitory activities for breast cancer therapy
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Hormone therapy targeting estrogen receptors is widely used clinically for the treatment of breast cancer, such as tamoxifen, but most of them are partial agonists, which can cause serious side effects after long-term use. The use of selective estrogen receptor down-regulators (SERDs) may be an effective alternative to breast cancer therapy by directly degrading ERα protein to shut down ERα signaling. However, the solely clinically used SERD fulvestrant, is low orally bioavailable and requires intravenous injection, which severely limits its clinical application. On the other hand, double- or multi-target conjugates, which are able to synergize antitumor activity by different pathways, thus may enhance therapeutic effect in comparison with single targeted therapy. In this study, we designed and synthesized a series of novel dual-functional conjugates targeting both ERα degradation and histone deacetylase inhibiton by combining a privileged SERD skeleton 7-oxabicyclo[2.2.1]heptane sulfonamide (OBHSA) with a histone deacetylase inhibitor side chain. We found that substituents on both the sulfonamide nitrogen and phenyl group of OBHSA unit had significant effect on biological activities. Among them, conjugate 16i with N-methyl and naphthyl groups exhibited potent antiproliferative activity against MCF-7 cells, and excellent ERα degradation activity and HDACs inhibitory ability. A further molecular docking study indicated the interaction patterns of these conjugates with ERα, which may provide guidance to design novel SERDs or PROTAC-like SERDs for breast cancer therapy.
- Zhao, Chenxi,Tang, Chu,Li, Changhao,Ning, Wentao,Hu, Zhiye,Xin, Lilan,Zhou, Hai-Bing,Huang, Jian
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- Z-Selective Fluoroalkenylation of (Hetero)Aromatic Systems by Iodonium Reagents in Palladium-Catalyzed Directed C?H Activation
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The direct and catalytic incorporation of fluorine containing molecular motifs into organic compounds resulting high-value added chemicals represents a rapidly evolving part of synthetic methodologies, thus this area is in the focus of pharmaceutical and agrochemical research. Herein we report a stereoselective procedure for direct fluorovinylation of aromatic and heteroaromatic scaffolds. This methodology development has been realized by palladium-catalyzed ortho C?H activation reaction of aniline derivatives featuring the regioselectivity via directing groups such as secondary of tertiary amides, ureas or ketones. The application of non-symmetrical aryl(fluoroalkenyl)-iodonium salts as fluoroalkenylating agents allowed mild reaction conditions in general for this transformation. The scope and limitations have been thoroughly investigated and the feasibility has been demonstrated by more than 50 examples.
- Bényei, Attila,Domján, Attila,Egyed, Orsolya,Gonda, Zsombor,Novák, Zoltán,Sályi, Gerg?,Tóth, Balázs L.
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supporting information
(2021/11/09)
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- An efficient, economical and eco-friendly acylation of alcohols and amines by alum doped nanopolyaniline under solvent free condition
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We report acylation of alcohols and amines employing acetic acid as an acylating agent in solvent free condition by using alum doped nanopolyaniline (NDPANI) as a catalyst. This environmentally benign method does not use corrosive acid anhydrides and acid chlorides for acylation and does not produce waste product. Also, a non-toxic potash alum was used for doping of polyaniline rather than corrosive acids. The reaction conditions represent an advance over established method not only in omitting the need for expensive catalysts or solvents but also in shortening the reaction time significantly. The advantages of this catalyst are non-hazardous, cheap, reusable, easy to prepare and handling.
- Behera, Satyaranjan,Patra, Braja N.
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- Hybrid quinoline-thiosemicarbazone therapeutics as a new treatment opportunity for Alzheimer’s disease-synthesis, in vitro cholinesterase inhibitory potential and computational modeling analysis
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Alzheimer’s disease (AD) is a progressive neurodegenerative disorder and the leading cause of dementia worldwide. The limited pharmacological approaches based on cholinesterase inhibitors only provide symptomatic relief to AD patients. Moreover, the adverse side effects such as nausea, vomiting, loss of appetite, muscle cramps, and headaches associated with these drugs and numerous clinical trial failures present substantial limitations on the use of medications and call for a detailed insight of disease heterogeneity and development of preventive and multifactorial therapeutic strategies on urgent basis. In this context, we herein report a series of quinoline-thiosemicarbazone hybrid therapeutics as selective and potent inhibitors of cholinesterases. A facile multistep synthetic approach was utilized to generate target structures bearing multiple sites for chemical modifications and establishing drug-receptor interactions. The structures of all the synthesized compounds were fully established using readily available spectroscopic techniques (FTIR, 1H- and 13C-NMR). In vitro inhibitory results revealed compound 5b as a promising and lead inhibitor with an IC50 value of 0.12 ± 0.02 μM, a 5-fold higher potency than standard drug (galantamine; IC50 = 0.62 ± 0.01 μM). The synergistic effect of electron-rich (methoxy) group and ethylmorpholine moiety in quinolinethiosemicarbazone conjugates contributes significantly in improving the inhibition level. Molecular docking analysis revealed various vital interactions of potent compounds with amino acid residues and reinforced the in vitro results. Kinetics experiments revealed the competitive mode of inhibition while ADME properties favored the translation of identified inhibitors into safe and promising drug candidates for pre-clinical testing. Collectively, inhibitory activity data and results from key physicochemical properties merit further research to ensure the design and development of safe and high-quality drug candidates for Alzheimer’s disease.
- Alsaab, Hashem O.,Aqsa, Sehar,Asif, Tahira Tasneem,Ibrar, Aliya,Kausar, Naghmana,Khan, Imtiaz,Munir, Rubina,Shahid, Noorma,Younas, Muhammad Tayyab,Zaib, Sumera
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- Method for catalyzing one-pot hydrogenation and amidation of nitroaromatic hydrocarbon and carboxylic acid by visible light
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The invention discloses a method for catalyzing one-pot hydrogenation and amidation reaction of nitroaromatic hydrocarbon and carboxylic acid by visible light. The method comprises the following steps: preparing Pt nanoparticles uniformly dispersed on an N-doped titanium dioxide/titanium carbide (MXene) heterojunction as a photocatalyst (3% Pt/N-TiO2/Ti3C2), and applying the catalyst to a cascade reaction of an aromatic nitro compound and carboxylic acid to prepare an amide product. The 3% Pt/N-TiO2/Ti3C2 has excellent tandem hydrogenation and amidation activity and chemical selectivity of an aromatic nitro compound and carboxylic acid under the irradiation of visible light. The excellent catalytic performance of 3% Pt/N-TiO2/Ti3C2 is attributed to the close contact of TiO2 and conductive Ti3C2, and the separation efficiency of photo-induced electrons and holes is improved through charge short-range directional transmission. The preparation method of the catalyst is simple and easy to operate, the catalyst can be used for photocatalytic efficient one-pot hydrogenation and amidation reactions, the reaction conditions are mild, and the catalyst is easy to recycle.
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Paragraph 0030
(2021/06/09)
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- Enhanced catalytic activity of one-dimensional CdS @TiO2 core-shell nanocomposites for selective organic transformations under visible LED irradiation
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In this study, we are interested in the photocatalytic activity under visible LED irradiation of one- dimensional (1D) CdS @TiO2 core–shell nanocomposites (CSNs) prepared through a facile and convenient method. For the synthesis of 1D CdS@TiO2 core/shell structure, titania source (Tetrabutyl titanate) was hydrolyzed by water vapor transmission on the surface of CdS nanowires (NWs) which were prepared via solvothermal method. The characterization of 1D CdS@TiO2 core–shell nanocomposites (CdS@TiO2 CSNs) was performed using X-ray diffraction (XRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM), UV–Vis spectroscopy, and UV–Vis diffuse reflectance spectroscopy (DRS). The as-synthesized sample was utilized for the selective reduction of nitro compounds to benzimidazole and anilide, and also the reduction of benzophenones to alcohol under blue LED irradiation. The 1D CdS@TiO2 CSNs exhibited enhanced photoactivity compared with the pure TiO2, CdS nanowires and commercial TiO2-P25. The excellent reusability of the photocatalyst was examined for six runs. The results demonstrated that the prepared sample has the potential to provide a promising visible light-driven photocatalyst for other organic transformations.
- Eskandari, Parvin,Kazemi, Foad,Ramdar, Moosa,Zand, Zahra
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- A novel construction of acetamides from rhodium-catalyzed aminocarbonylation of DMC with nitro compounds
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Dimethyl carbonate (DMC), an environment-friendly compound prepared from CO2, shows diverse reactivities. In this communication, an efficient procedure using DMC as both a C1 building block and solvent in the aminocarbonylation reaction with nitro compounds has been developed. W(CO)6acts both a CO source and a reductant here.
- Bao, Zhi-Peng,Miao, Ren-Guan,Qi, Xinxin,Wu, Xiao-Feng
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supporting information
p. 1955 - 1958
(2021/03/02)
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- Hypervalent Iodine Reagent-Promoted Hofmann-Type Rearrangement/Carboxylation of Primary Amides
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A novel transformation of primary amides to secondary amides promoted by hypervalent iodine reagents was developed. The hypervalent iodine reagent-mediated Hofmann-type rearrangement generated an isocyanate intermediate, which was subsequently trapped by an in situ generated carboxylic acid from the hypervalent iodine reagent to provide the corresponding secondary amides. This method provided a facile and efficient route for the synthesis of secondary amides from primary amides and also revealed novel reactivities of hypervalent iodine reagents.
- Wang, Xia,Yang, Peng,Hu, Bo,Zhang, Qian,Li, Dong
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p. 2820 - 2826
(2021/02/01)
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- Visible-light induced one-pot hydrogenation and amidation of nitroaromatics with carboxylic acids over 2D MXene-derived Pt/N-TiO2/Ti3C2
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Pt nanoparticles supported on N doped titanium dioxide/titanium carbide (MXene) heterojunctions were employed as photocatalysts for the tandem reactions between aromatic nitro compounds and carboxylic acids to produce amide products. The 3%Pt/N-TiO2/Ti3C2 heterojunction was prepared by in situ grew TiO2 on Ti3C2 nanosheets and then N doped TiO2 with melamine, Pt nanoparticles with 3.3 nm mean diameter well dispersed on N-TiO2/Ti3C2. 3%Pt/N-TiO2/Ti3C2 had excellent amidation activity and chemoselectivity under visible-light irradiation. The elevated catalytic performance of 3%Pt/N-TiO2/Ti3C2 was owing to the improvement in photogenerated electron and hole separation efficiency through charge short-range directional transmission caused by the intimate contact between the TiO2 and the conductive Ti3C2. This direct hydrogenation along with amidation between nitroaromatics and carboxylic acids own actual merits in the amides produce with no harmful byproducts. In situ DRIFTS spectra verified that the amidation activation with visible light irradiation at 25 °C was much faster than heating.
- Jiang, Heyan,Hu, Zujie,Gan, Chuan,Sun, Bin,Kong, Shuzhen,Bian, Fengxia
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- Nitromethane as a nitrogen donor in Schmidt-type formation of amides and nitriles
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The Schmidt reaction has been an efficient and widely used synthetic approach to amides and nitriles since its discovery in 1923. However, its application often entails the use of volatile, potentially explosive, and highly toxic azide reagents. Here, we report a sequence whereby triflic anhydride and formic and acetic acids activate the bulk chemical nitromethane to serve as a nitrogen donor in place of azides in Schmidt-like reactions. This protocol further expands the substrate scope to alkynes and simple alkyl benzenes for the preparation of amides and nitriles.
- Jiao, Ning,Liu, Jianzhong,Qiu, Xu,Song, Song,Wei, Jialiang,Wen, Xiaojin,Zhang, Cheng,Zhang, Ziyao
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supporting information
p. 281 - 285
(2020/01/28)
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- Tin(ii) chloride dihydrate/choline chloride deep eutectic solvent: Redox properties in the fast synthesis of: N -arylacetamides and indolo(pyrrolo)[1,2- a] quinoxalines
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In this contribution a physicochemical, IR and Raman characterization for the tin(ii) chloride dihydrate/choline chloride eutectic mixture is reported. The redox properties of this solvent were also studied by cyclic voltammetry finding that it can be successfully used as an electrochemical solvent for electrosynthesis and electroanalytical processes and does not require negative potentials as verified by the reduction of nitrobenzene. The potential use of this eutectic mixture as a redox solvent was further explored in obtaining aromatic amines and N-arylacetamides starting from a wide variety of nitroaromatic compounds. In addition, a fast synthetic strategy for the construction of a series of indolo(pyrrolo)[1,2-a]quinoxalines was developed by reacting 1-(2-nitrophenyl)-1H-indole(pyrrole) with aldehydes. This simple protocol offers a straightforward method for the construction of the target quinoxalines in short reaction times and high yields where the key step involves a tandem one-pot reductive cyclization-oxidation.
- Bejarano, Oscar Rodríguez,Ochoa-Puentes, Cristian,Pe?a-Solórzano, Diana,Trujillo, Sergio Alfonso
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p. 40552 - 40561
(2020/11/18)
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- The immobilized copper species on nickel ferrite (NiFe2O4@Cu): a magnetically reusable nanocatalyst for one-pot and quick reductive acetylation of nitroarenes to N-arylacetamides
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In this study, a green protocol for synthesis of N-arylacetamides was introduced. Magnetically, nanoparticles of the immobilized copper species on nickel ferrite, NiFe2O4@Cu, were synthesized and then characterized using SEM, EDX, XRD, VSM, ICP-OES, BET and XPS analyses. The XPS analysis approved that the immobilized copper species on NiFe2O4 only contain Cu(0) and its oxide form as CuO. The prepared nanocomposite system represented a perfect catalytic activity toward one-pot and quick reductive acetylation of various nitroarenes to the corresponding N-arylacetamides. All reactions were carried out in a mixture of H2O–EtOH (1.5–0.5) within 2–10?min using the combination system of NaBH4 and Ac2O in a one-pot approach and via a two-step procedure. The utilized Cu nanocomposite was magnetically separated from the reaction mixture and reused for 5 consecutive cycles without the significant loss of its catalytic activity.
- Zeynizadeh, Behzad,Shokri, Zahra,Mohammadzadeh, Iman
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p. 859 - 870
(2019/12/24)
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- The immobilized Cu nanoparticles on magnetic montmorillonite (MMT?Fe3O4?Cu): As an efficient and reusable nanocatalyst for reduction and reductive-acetylation of nitroarenes with NaBH4
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In this study, the immobilization of copper nanoparticles on superparamagnetic montmorillonite, MMT?Fe3O4?Cu, was studied. Magnetically nanoparticles (MNPs) of iron oxide (Fe3O4) were primarily prepared by a chemical co-precipitation method. Next, the prepared Fe3O4 MNPs were intercalated within the interlamellar spaces and external surface of sodium-exchanged montmorillonite. Finally, Cu NPs were immobilized on magnetic montmorillonite by a simply mixing of an aqueous solution of CuCl2·2H2O with MMT?Fe3O4 followed by the reduction with NaBH4. Characterization of MMT?Fe3O4 clay system represented that through the immobilization of Fe3O4 MNPs, disordered-layers structure of MMT was easily reorganized to an ordered-layers arrangement. The synthesized composite systems were characterized using FT-IR, SEM, EDX, XRD, VSM, BET and ICP-OES analyses. SEM analysis exhibited that dispersion of Cu NPs, with the size distribution of 15–25 nm, on the surface of magnetic clay was taken place perfectly. BET surface analysis indicated that after the immobilization of Fe3O4 and Cu species, the surface area and total pore volume of MMT?Fe3O4?Cu system was decreased. Next, the Cu-clay nanocomposite system showed a perfect catalytic activity towards reduction of nitroarenes to anilines as well as reductive-acetylation of nitroarenes to acetanilides using NaBH4 and Ac2O in water as a green and economic solvent. The copper magnetic clay catalyst can be easily separated from the reaction mixture by an external magnetic field and reused for six consecutive cycles without the significant loss of its catalytic activity.
- Zeynizadeh, Behzad,Rahmani, Soleiman,Tizhoush, Hengameh
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- An Electrochemical Beckmann Rearrangement: Traditional Reaction via Modern Radical Mechanism
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Abstract: Electrosynthesis as a potential means of introducing heteroatoms into the carbon framework is rarely studied. Herein, the electrochemical Beckmann rearrangement, i. e. the direct electrolysis of ketoximes to amides, is presented for the first time. Using a constant current as the driving force, the reaction can be easily carried out under neutral conditions at room temperature. Based on a series of mechanistic studies, a novel radical Beckmann rearrangement mechanism is proposed. This electrochemical Beckmann rearrangement does not follow the trans-migration rule of the classical Beckmann rearrangement.
- Tang, Li,Wang, Zhi-Lv,He, Yan-Hong,Guan, Zhi
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p. 4929 - 4936
(2020/08/21)
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- Rhodium-Catalyzed Addition of Organozinc Iodides to Carbon-11 Isocyanates
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Amides were prepared using rhodium-catalyzed coupling of organozinc iodides and carbon-11 (11C, t1/2 = 20.4 min) isocyanates. Nonradioactive isocyanates and sp3 or sp2 organozinc iodides generated amides in yields of 13%-87%. Incorporation of cyclotron-produced [11C]CO2 into 11C-amide products proceeded in yields of 5%-99%. The synthetic utility of the methodology was demonstrated through the isolation of [11C]N-(4-fluorophenyl)-4-methoxybenzamide ([11C]6g) with a molar activity of 267 GBq μmol-1 and 12% radiochemical yield in 21 min from the beginning of synthesis.
- Fouad, Moustafa H.,Ismailani, Uzair S.,Mair, Braeden A.,Munch, Maxime,Rotstein, Benjamin H.
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supporting information
p. 2746 - 2750
(2020/04/16)
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- Design, synthesis and biological evaluation of novel 5-((substituted quinolin-3-yl/1-naphthyl) methylene)-3-substituted imidazolidin-2,4-dione as HIV-1 fusion inhibitors
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A series of novel 5-(substituted quinolin-3-yl or 1-naphthyl)methylene)-3-substituted imidazolidin-2,4-dione 9–26 was designed and synthesized. The prepared compounds were identified using 1H NMR, 13C NMR as well as elemental analyses. The inhibitory activity of 9–26 on HIV-1IIIB replication in MT-2 cells was evaluated. Some derivatives showed good to excellent anti-HIV activities as compounds 13, 18, 19, 20, 22 and 23. They showed EC50 of 0.148, 0.460, 0.332, 0.50, 0.271 and 0.420 μM respectively being more potent than compound I (EC50 = 0.70 μM) and II ( EC50 = 2.40 μM) as standards. The inhibitory activity of 9–26 on infected primary HIV-1 domain, 92US657 (clade B, R5) was investigated. All the tested compounds consistently inhibited infection of this virus with EC50 from 0.520 to 11.857 μM. Results from SAR studies showed that substitution on ring A with 6/7/8-methyl group resulted in significant increase in the inhibitory activity against HIV-1IIIB infection (5- >300 times) compared to the unsubstituted analog 9. The cytotoxicity of these compounds on MT-2 cells was tested and their CC50 values ranged from 11 to 85 μM with selectivity indexes ranged from 0.53 to 166. The docking study revealed nice fitting of the new compounds into the hydrophobic pocket of HIV-1 gp41 and higher affinity than NB-64. Compound 13, the most active in preventing HIV-1IIIB infection, adopted a similar orientation to compound IV. Molecular docking analysis of the new compounds revealed hydrogen bonding interactions between the imidazolidine-2,4-dione ring and LYS574 which were missed in the weakly active derivatives.
- AL-Mahmoudy, Amany M. M.,Abdel-Aal, Eatedal H.,AlAwadh, Mohammed A.,Alhakamy, Nabil A.,Asfour, Hany Z.,Bokhtia, Riham M.,Elagawany, Mohamed,Gouda, Ahmed M.,Ibrahim, Tarek S.,Panda, Siva,Taher, Ehab S.,Youssif, Bahaa G. M.
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- Design and synthesis of novel pyrazolo[3,4-d]pyrimidin-4-one bearing quinoline scaffold as potent dual PDE5 inhibitors and apoptotic inducers for cancer therapy
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PDE5 targeting represents a new and promising strategy for apoptosis induction and inhibition of tumor cell growth due to its over-expression in diverse types of human carcinomas. Accordingly, we report the synthesis of series of pyrazolo[3,4-d]pyrimidin-4-one carrying quinoline moiety (11a-r) with potential dual PDE5 inhibition and apoptotic induction for cancer treatment. These hybrids were structurally elucidated and characterized with variant spectroscopic techniques as 1H NMR, 13C NMR and elemental analysis. The assessment of their anticancer activities has been declared. All the rationalized compounds 11a-r have been selected for their cytotoxic activity screening by NCI against 60 cell lines. Compounds 11a, 11b, 11j and 11k were the most active hybrids. Among all, compound 11j was further selected for five dose tesing and it displayed outstanding activity with strong antitumor activity against the nine tumor subpanels tested with selectivity ratios ranging from 0.019 to 8.3 at the GI50 level. Further, the most active targets 11a, b, j and k were screened for their PDE5 inhibitory activity, compound 11j (with IC50 1.57 nM) exhibited the most potent PDE5 inhibitory activity. Moreover, compound 11j is also showed moderate EGFR inhibition with IC50 of 5.827 ± 0.46 μM, but significantly inhibited the Wnt/β-catenin pathway with IC501286.96 ± 12.37 ng/mL. In addition, compound 11j induced the intrinsic apoptotic mitochondrial pathway in HepG2 cells as evidenced by the lower expression levels of the anti-apoptotic Bcl-2 protein, and the higher expression of the pro-apoptotic protein Bax, p53, cytochrome c and the up-regulated active caspase-9 and caspase-3 levels. All results confirmed by western blotting assay. Compound 11j exhibit pre G1 apoptosis and cell cycle arrest at G2/M phase. In conclusion, hybridization of quinoline moiety with the privileged pyrazolo[3,4-d]pyrimidinon-4-one structure resulted in highly potent anticancer agent, 11j, which deserves more study, in particular, in vivo and clinical investiagtions, and it is expected that these results would be applied for more drug discovery process.
- Ibrahim, Tarek S.,Hawwas, Mohamed M.,Taher, Ehab S.,Alhakamy, Nabil A.,Alfaleh, Mohamed A.,Elagawany, Mohamed,Elgendy, Bahaa,Zayed, Gamal M.,Mohamed, Mamdouh F.A.,Abdel-Samii, Zakaria K.,Elshaier, Yaseen A.M.M.
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- Potent quinoline-containing combretastatin a-4 analogues: Design, synthesis, antiproliferative, and anti-tubulin activity
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A novel series of quinoline derivatives of combretastatin A-4 incorporating rigid hydrazone and a cyclic oxadiazole linkers were synthesized and have demonstrated potent tubulin polymerization inhibitory properties. Many of these novel derivatives have shown significant antiproliferative activities in the submicromolar range. The most potent compound, 19h, demonstrated superior IC50 values ranging from 0.02 to 0.04 μM against four cancer cell lines while maintaining low cytotoxicity in MCF-10A non-cancer cells, thereby suggesting 19h’s selectivity towards proliferating cancer cells. In addition to tubulin polymerization inhibition, 19h caused cell cycle arrest in MCF-7 cells at the G2/M phase and induced apoptosis. Collectively, these findings indicate that 19h holds potential for further investigation as a potent chemotherapeutic agent targeting tubulin.
- Ibrahim, Tarek S.,Hawwas, Mohamed M.,Malebari, Azizah M.,Taher, Ehab S.,Omar, Abdelsattar M.,O’boyle, Niamh M.,McLoughlin, Eavan,Abdel-Samii, Zakaria K.,Elshaier, Yaseen A. M. M.
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- Visible Light-Induced Amide Bond Formation
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A metal-, base-, and additive-free amide bond formation reaction was developed under an organic photoredox catalyst. This green approach showed excellent functional selectivity without affecting other functional groups such as alcohols, phenols, ethers, esters, halogens, or heterocycles. This method featured a broad substrate scope, good compatibility with water and air, and high yields (≤95%). The potential utilities were demonstrated by the synthesis of important drug molecules such as paracetamol, melatonin, moclobemide, and acetazolamide.
- Song, Wangze,Dong, Kun,Li, Ming
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supporting information
p. 371 - 375
(2019/11/29)
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- Method for preparing amide by visible light-induced metal-free participation (by machine translation)
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The method for preparing the amide in the, preparation method of the novel amide disclosed by the invention has the advantages that, the reaction: conditions are mild, the 9 - reaction conditions are mild, and the yield 71%. of the reaction conditions is not lower than the reaction conditions . (by machine translation)
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Paragraph 0047-0050
(2020/02/14)
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- Visible-light-induced Beckmann rearrangement by organic photoredox catalysis
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A facile and general strategy for efficient direct conversion of oximes to amides using an inexpensive organic photocatalyst and visible light is described. This radical Beckmann rearrangement can be performed under mild conditions. Various alkyl aryl ketoximes and diaryl ketoximes can be effectively converted into the corresponding amides in excellent yields.
- Tang, Li,Wang, Zhi-Lv,Wan, Hai-Lan,He, Yan-Hong,Guan, Zhi
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supporting information
p. 6182 - 6186
(2020/09/01)
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- Iodine and Br?nsted acid catalyzed C–C bond cleavage of 1,3-diketones for the acylation of amines
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A metal-free N-acylation method of anilines with 1,3-diketones has been developed, by using iodine and p-toluene sulfonic acid as the co-catalysts. The reaction can proceed in 1,4-dioxane at elevated temperature to produce the corresponding amides with 48–89% yields. Further, the gram-scale experiment was carried out under the standard conditions and the possible mechanism was proposed.
- Zhou, Xiao-Yu,Chen, Xia,Yang, Dan
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supporting information
p. 177 - 184
(2019/11/26)
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- New half-sandwich (η6-p-cymene)ruthenium(II) complexes with benzothiazole hydrazone Schiff base ligand: Synthesis, structural characterization and catalysis in transamidation of carboxamide with primary amines
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Few half-sandwich (η6-p-cymene) ruthenium(II) complexes supported by benzothiazole hydrazone Schiff bases were synthesized. The new complexes possess the general formulae [Ru(η6-p-cymene)(L)Cl] (1-3) (L = salicyl((2-(benzothiazol-2-yl)hydrazono)methylphenol) (SAL-HBT), 2-((2-(benzothiazol-2-yl)hydrazono)methyl)-6 methoxyphenol) (VAN-HBT) or naphtyl-2-((2-(benzothiazol-2-yl)hydrazono)methyl phenol) (NAP-HBT). All compounds were fully studied by analytical, spectroscopic techniques (IR, NMR) and also by mass spectrometry. The solid state structure of the complex 3 reveals the coordination of p-cymene moieties with ruthenium(II) in a three-legged piano-stool geometry along with benzothiazole hydrazone Schiff base ligand in a monobasic bidentate fashion. The catalytic properties of the complexes were screened in transamidation of primary amide with amines after optimization with respect to solvent, substituents, time and catalyst loading. The results show that the complex 3 is the most efficient catalyst for the transamidation of carboxamides with amines.
- Vijayapritha, Subbarayan,Viswanathamurthi, Periasamy
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supporting information
(2020/10/18)
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- Acylation of Phenols, Alcohols, Thiols, Amines and Aldehydes Using Sulfonic Acid Functionalized Hyper-Cross-Linked Poly(2-naphthol) as a Solid Acid Catalyst
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Abstract: The hyper-cross-linked porous poly(2-naphthol) fabricated by the Friedel–Crafts alkylation of 2-naphthol has been functionalized with sulfonic acid to obtain a solid acid catalyst. The catalyst is applied for the protection of phenol, alcohols, thiols, amines and aldehydes with acetic anhydride at room temperature. The catalytic protection using the new solid acid is featured by achieving high yield at neat condition, needing no aqueous work-up and/or chromatographic separation, and showing excellent recycling efficiency, suggesting the potential of this sulfonated porous polymers as a new protection protocol in a wide range of sustainable chemical reactions. Graphical Abstract: [Figure not available: see fulltext.].
- Kalla, Reddi Mohan Naidu,Reddy, Sirigireddy Sudharsan,Kim, Il
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p. 2696 - 2705
(2019/05/28)
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- Rhodium(III)-Catalyzed Directed C-H Dienylation of Anilides with Allenes Leads to Highly Conjugated Systems
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Allenes are unique coupling partners in transition-metal-catalyzed C-H functionalization leading to a variety of products via alkenylation, allenylation, allylation, and annulation reactions. The outcome is governed by both the reactivity of the allene and the formation and stability of the organometallic intermediate. An efficient Rh(III)-catalyzed, weakly coordinating group-directed dienylation of electronically unbiased allenes is developed using an N-acyl amino acid as a ligand. Further elaboration of the dienylated products to construct polycyclic compounds is also described.
- Ghosh, Chiranjit,Nagtilak, Prajyot Jayadev,Kapur, Manmohan
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supporting information
(2019/05/08)
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- Method for preparing CLT acid by taking m-toluidine as raw material
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The invention discloses a method for preparing CLT acid by taking m-toluidine as a raw material, and belongs to the field of chemical synthesis. The method solves the problems that existing CLT acid production is low in yield, not environmentally friendly and the like. The method comprises: S01) an acylation step, namely a step of reacting m-toluidine and acetic anhydride to obtain acylation reaction solution; S02) a chlorination step, namely a step of adding acetic acid and concentrated hydrochloric acid into the acylation reaction solution, then adding hydrogen peroxide, and finally adding an aqueous solution containing sodium sulfite to obtain a chlorination reaction solution; S03) a hydrolyzing step to form salt, namely a step of adding concentrated sulfuric acid into the chlorinationreaction solution, and removing the solvent after reaction; S04) a transposition sulfonation step, namely a step of adding chlorobenzene into the solvent-removed reaction solution obtained in the stepS03, heating the mixture, adding dichlorobenzene, heating the mixture again, reacting the mixture for 7-10 hours with the temperature of the system being maintained at a temperature higher than 170 DEG C, and stopping heating; and S05) a step of post-treatment to obtain a finished product that is the CLT acid. The method has the advantages of environmental protection and the like.
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Paragraph 0053-0055
(2019/12/02)
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- Quinoline Based Monocarbonyl Curcumin Analogs as Potential Antifungal and Antioxidant Agents: Synthesis, Bioevaluation and Molecular Docking Study
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In search for new fungicidal and free radical scavenging agents, we synthesized a focused library of 2-chloroquinoline based monocarbonyl analogs of curcumin (MACs). The synthesized MACs were evaluated for in vitro antifungal and antioxidant activity. The antifungal activity was evaluated against five different fungal strains such as Candida albicans, Fusarium oxysporum, Aspergillus flavus, Aspergillus niger, and Cryptococcus neoformans, respectively. Most of the synthesized MACs displayed promising antifungal activity compared to the standard drug Miconazole. Furthermore, molecular docking study on a crucial fungal enzyme sterol 14α-demethylase (CYP51) could provide insight into the plausible mechanism of antifungal activity. MACs were also screened for in vitro radical scavenging activity using butylated hydroxytoluene (BHT) as a standard. Almost all MACs exhibited better antioxidant activity compared to BHT.
- Akolkar, Satish V.,Khedkar, Vijay M.,Nagargoje, Amol A.,Sangshetti, Jaiprakash N.,Shingate, Bapurao B.,Siddiqui, Madiha M.,Subhedar, Dnyaneshwar D.
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- Synthesis of diverse libraries of carboxamides via chemoselective N-acylation of amines by carboxylic acids employing Br?nsted acidic IL [BMIM(SO3H)][OTf]
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Chemoselective N-acylation of amines with carboxylic acids as acyl electrophiles and Br?nsted acidic IL [BMIM(SO3H)][OTf] as promoter is reported under both thermal and microwave irradiation to produce libraries of carboxamides in good to excellent yields after a simple workup. The protocol is compatible with structurally diverse 1° and 2° amines and works in the presence of sensitive functional groups such as thiols and phenols. The potential for recycling and reuse of the IL is also demonstrated.
- Savanur, Hemantkumar M.,Malunavar, Shruti S.,Prabhala, Pavankumar,Sutar, Suraj M.,Kalkhambkar, Rajesh G.,Laali, Kenneth K.
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supporting information
(2019/09/30)
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- The immobilized Ni(II)-thiourea complex on silica-layered copper ferrite: A novel and reusable nanocatalyst for one-pot reductive-acetylation of nitroarenes
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In this study, magnetically nanoparticles of CuFe2O4@SiO2@PTMS@Tu@Ni(II) as novel and reusable catalyst were prepared. Synthesis of the Ni (II)-nanocatalyst was carried out through the complexation of Ni(OAc)2·4H2O with the immobilized thiourea on silica-layered CuFe2O4. The prepared nanocomposite system was then characterized using SEM, EDX, XRD, VSM, ICP-OES, Raman, UV–Vis and FT-IR analyses. Catalytic activity of the Ni(II)-CuFe2O4 system was investigated towards rapid reduction of aromatic nitro compounds to arylamines with sodium borohydride as well as one-pot reductive-acetylation of nitroarenes to acetanilides with NaBH4/Ac2O system without the isolation of intermediate arylamines. All reactions were carried out in H2O within 3–7?min to afford the products arylamines/acetanilides in high to excellent yields. Reusability of the Ni(II)-nanocatalyst was examined for seven consecutive cycles without the significant loss of the catalytic activity.
- Zeynizadeh, Behzad,Shokri, Zahra,Hasanpour Galehban, Morteza
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- Visible Light-Promoted Beckmann Rearrangements: Separating Sequential Photochemical and Thermal Phenomena in a Continuous Flow Reactor
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The Beckmann rearrangement of oximes to amides typically requires strong acids or highly reactive, hazardous electrophiles and/or elevated temperatures to proceed. A very attractive alternative is the in situ generation of Vilsmeier–Haack reagents, by means of photoredox catalysis, as promoters for the thermal Beckmann rearrangement. Investigation of the reaction parameters for this light-induced method using a one-pot strategy has shown that the reaction is limited by the different temperatures required for each of the two sequential steps. Using a continuous flow reactor, the photochemical and thermal processes have been separated by integrating a flow photoreactor unit at low temperature for the electrophile generation with a second reactor unit, at high temperature, where the rearrangement takes place. This strategy has enabled excellent conversions and yields for a diverse set of oximes, minimizing the formation of side products obtained with the original one-pot method.
- Chen, Yuesu,Cantillo, David,Kappe, C. Oliver
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supporting information
p. 2163 - 2171
(2019/03/14)
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- Amide Synthesis from Thiocarboxylic Acids and Amines by Spontaneous Reaction and Electrosynthesis
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Amide bond formation is one of the most important basic reactions in chemistry. A catalyst-free approach for constructing amide bonds from thiocarboxylic acids and amines was developed. The mechanistic studies showed that the disulfide was the key intermediate for this amide synthesis. Thiobenzoic acids could be automatically oxidized to disulfides in air, thioaliphatic acids could be electro-oxidized to disulfides, and the resulting disulfides reacted with amines to give the corresponding amides. By this method, various amides could be easily synthesized in excellent yields without using any catalyst or activator. The successful synthesis of bioactive compounds also highlights the synthetic utility of this strategy in medicinal chemistry.
- Tang, Li,Matuska, Jack H.,Huang, Yu-Han,He, Yan-Hong,Guan, Zhi
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p. 2570 - 2575
(2019/06/13)
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- Copper-Catalyzed Acetylation of Electron-Rich Phenols and Anilines
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An approach has been developed for the copper-catalyzed acetylation of phenols and anilines with potassium thioacetate as an acetylating reagent. Although only electron-rich phenols and anilines are compatible with this protocol, the reaction can provide moderate to high yields under mild conditions. Compared with other acetylating reagents, the current reagent has certain advantages, such as its low cost, easy availability, stability, insensitivity to water or air, and ease of storage.
- Zhang, Jieyu,Ke, Qiumin,Tian, Feitao,Jiang, Bei,Ji, Chang-An,Zhang, Lingling,Yu, Jian,Huang, Dayun,Yan, Guobing
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supporting information
p. 726 - 730
(2019/03/26)
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- Potassium tert-Butoxide Prompted Highly Efficient Transamidation and Its Coordination Radical Mechanism
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A simple and highly efficient protocol was developed for the transamidation of N,N-disubstituted amides with primary amines in the presence of tBuOK, affording desired products in good to excellent yields. This reaction proceeded under nitrogen atmosphere and featured extensive substrate tolerance. Experimental investigation suggested that a coordination radical process enhanced this transformation.
- Tan, Zhiyong,Li, Zhenhua,Ma, Yao,Qin, Jinjing,Yu, Chuanming
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p. 4538 - 4545
(2019/07/18)
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- Synthesis of acetamides from aryl amines and acetonitrile by diazotization under metal-free conditions
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An efficient and metal-free coupling reaction has been developed that affords acetamides from the corresponding aryl amines and acetonitrile. This method tolerates a wide range of functional groups and is selective toward aryl amines. Preliminary mechanistic studies were conducted.
- Duan, Pan,Guo, Yu,Kang, Huan,Li, Yi-Na,Wen, Xianghao,Xiao, Fang,Zeng, Yao-Fu,Zhang, Na-Na
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supporting information
p. 2169 - 2172
(2019/11/25)
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- METHOD FOR PRODUCING AMIDE COMPOUND
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PROBLEM TO BE SOLVED: To provide a novel method for producing an amide compound which does not require severe reacting conditions without directly using hydroxylamine and its derivative. SOLUTION: There is provided a method for producing an amide compound which comprises: a step of transferring a ketone compound and an oxime compound to oxime in the presence of an organic solvent and an acid catalyst; and a step of subjecting the oxime to Beckmann rearrangement. The acid catalyst preferably is hydrochloric acid, sulfuric acid, methanesulfonic acid, tosyl acid monohydrate, trifluoromethanesulfonic acid, bistrifluoromethane sulfonimide, a boron trifluoride-diethyl ether complex, scandium trifluoromethanesulfonate (III), iron trifluoromethanesulfonate (III), copper trifluoromethanesulfonate (II), bismuth(III) trifluoromethanesulfonate, titanium tetrachloride or iron trichloride. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT
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Paragraph 0029; 0031
(2018/09/30)
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- Direct and Catalytic Amide Synthesis from Ketones via Transoximation and Beckmann Rearrangement under Mild Conditions
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The Br?nsted acid-catalyzed synthesis of secondary amides from ketones under mild conditions is described via transoximation and Beckmann rearrangement using O-protected oximes as more stable equivalents of explosive O-protected hydroxylamines. This methodology could be applied to highly rearrangement-selective amide synthesis from α-branched alkyl aryl ketones and performed on a 1-g scale. The presence of water is essential for this reaction, and its role was clarified by isotope-labeling experiments.
- Hyodo, Kengo,Hasegawa, Genna,Oishi, Naoki,Kuroda, Kazuma,Uchida, Kingo
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p. 13080 - 13087
(2018/11/02)
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- Sulfonium Salts as Alkylating Agents for Palladium-Catalyzed Direct Ortho Alkylation of Anilides and Aromatic Ureas
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A novel method for the ortho alkylation of acetanilide and aromatic urea derivatives via C-H activation was developed. Alkyl dibenzothiophenium salts are considered to be new reagents for the palladium-catalyzed C-H activation reaction, which enables the transfer of methyl and other alkyl groups from the sulfonium salt to the aniline derivatives under mild catalytic conditions.
- Simkó, Dániel Cs.,Elekes, Péter,Pázmándi, Vivien,Novák, Zoltán
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supporting information
p. 676 - 679
(2018/02/09)
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- Synthesis of magnetic Fe3O4@SiO2@Cu–Ni–Fe–Cr LDH: an efficient and reusable mesoporous catalyst for reduction and one-pot reductive-acetylation of nitroarenes
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Abstract: Magnetically recoverable Fe3O4@SiO2@Cu–Ni–Fe–Cr LDH was prepared under co-precipitation conditions. Characterization of the mesoporous catalyst was confirmed using Fourier-transformed infrared spectroscopy, scanning electron microscopy, energy-dispersive X-ray spectroscopy, X-ray diffraction, vibration sample magnetometer, Brunauer–Emmett–Teller, thermogravimetric, differential thermogravimetric analyses and transmission electron microscopy. Reduction of nitroarenes to the corresponding arylamines and one-pot reductive-acetylation of nitroarenes to acetanilides were carried out successfully by nanoparticles of the immobilized Cu–Ni–Fe–Cr layered double hydroxide on silica-coated Fe3O4 in water as a green solvent. All reactions were carried out within 6–22?min affording arylamines and N-arylacetamides in high-to-excellent yields. Reusability of the core–shell nanocatalyst was examined six times without significant loss of its catalytic activity.
- Gilanizadeh, Masumeh,Zeynizadeh, Behzad
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p. 2821 - 2837
(2018/10/31)
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- Ni2B@Cu2O and Ni2B@CuCl2: two new simple and efficient nanocatalysts for?the green one-pot reductive acetylation of nitroarenes and direct N-acetylation of arylamines using solvent-free mechanochemical grinding
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Abstract: Ni2B@Cu2O and Ni2B@CuCl2 are introduced as simple and efficient earth-abundant transition-metal-based nanocomposites for the?green one-pot reductive acetylation of aromatic nitro compounds and direct N-acetylation of arylamines using a solvent-free mechanochemical grinding technique. The designed Ni2B-based nanocomposites were characterized by Fourier-transform infrared (FT-IR) spectroscopy, X-ray diffraction (XRD) analysis, and scanning electron microscopy (SEM) with energy-dispersive X-ray (EDX) spectroscopy. Notable advantages of these methods include broad substrate scope, use of a solvent-free mechanochemical grinding technique, implementation of earth-abundant transition-metal-based nanocomposites as simple and practical catalysts, and short reaction time and high yield at ambient condition. The mentioned methods can also be successfully applied for the?synthesis of a broad range of other amides (especially substituted acetamides) using green chemistry protocols. Also, the recoverability and reusability of the mentioned new nanocomposites were investigated. Graphical abstract: [Figure not available: see fulltext.].
- Zeynizadeh, Behzad,Younesi, Reza,Mousavi, Hossein
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p. 7331 - 7352
(2018/08/25)
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- Imidazolium chloride: An efficient catalyst for transamidation of primary amines
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A highly efficient and convenient protocol of imidazolium chloride (30 mol %) catalyzed amidation of amines with moderate to excellent yields was reported. The protocol shows broad substrate scope for aromatic, aliphatic, and heterocyclic primary amines.
- Tian, Qingqiang,Gan, Zongjie,Wang, Xuetong,Li, Dan,Luo, Wen,Wang, Huajun,Dai, Zeshu,Yuan, Jianyong
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supporting information
(2018/09/10)
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- Palladium(II)-Catalyzed Oxidative Homo- and Cross-Coupling of Aryl ortho -sp2 C-H Bonds of Anilides at Room Temperature
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The preparation of secondary 2,2'-bisanilides has been successfully achieved through an oxidative coupling of aryl ortho-sp2 C-H bonds of anilides in the presence of catalytic Pd(OAc)2 and K2S2O8 as an oxidant in MsOH/CF3CO2H (TFA) at room temperature (25 °C). The aromatic rings of anilides substituted by various electron-donating or electron-withdrawing groups are tolerant in these coupling reactions.
- Mei, Chong,Lu, Wenjun
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p. 4812 - 4823
(2018/04/26)
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- Synthesis of oxindole from acetanilide via Ir(iii)-catalyzed C-H carbenoid functionalization
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Herein we disclose the first report on the synthesis of oxindole derivatives from acetanilide via Ir(iii)-catalyzed intermolecular C-H functionalization with diazotized Meldrum's acid. A broad range of substituted anilides were found to react smoothly under the Ir(iii)-catalytic system to afford the corresponding N-protected oxindoles. The N-protecting groups, such as Ac, Bz or Piv, can be easily removed to furnish the oxindole. Various synthetic applications of the synthesized oxindole were also demonstrated.
- Patel, Pitambar,Borah, Gongutri
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supporting information
p. 443 - 446
(2017/01/03)
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- Impregnated copper on Fe3O4: an efficient magnetically separable nanocatalyst for rapid and selective acylation of amines
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The present paper describes the synthesis of N-arylacetamides through acetylation of arylamines with Ac2O in the presence of magnetically recyclable Fe3O4/Cu NPs. All reactions were carried out efficiently in H2O within 2–10?min to give the products in 89–95% yields. Selective acetylation of amines versus alcohols was carried out successfully with this acetylating system. In addition, acetylation of amines and phenols was taken place with the same reactivity. Reusability of the nanocatalyst was examined 5 times without significant loss of its catalytic activity.
- Shokri, Zahra,Zeynizadeh, Behzad
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p. 2467 - 2474
(2017/10/30)
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- Co3O4 nanoparticles prepared by oxidative precipitation method: an efficient and reusable heterogeneous catalyst for N-formylation of amines
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Abstract: N-formylation of different amines was carried out with formic acid in the presence of the Co3O4 nanoparticles as an efficient, stable heterogeneous catalyst to give the corresponding formamides under solvent-free conditions. This method has advantages over the reported methods such as high yields, mild conditions, easy work-up and short reaction times. The catalyst was characterized by different techniques such as XRD, SEM and FT-IR spectroscopy. Graphical Abstract: [Figure not available: see fulltext.]
- Marjani, Ahmad Poursattar,Hosseini, Seyed Ali,Shokri, Zahra,Maleki, Nasim
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p. 413 - 422
(2017/01/14)
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- Sulfated choline ionic liquid-catalyzed acetamide synthesis by grindstone method
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Sulfated choline ionic liquid (SCIL) has been found to be an efficient solid acid IL catalyst for the protection of amine groups with acetic anhydride under solvent-free grindstone conditions. The attractive features of this new catalytic methodology include its sustainability, facile work-up procedure, economic viability, and biodegradability. The SCIL catalyst was characterized using infrared spectroscopy, wide-angle X-ray scattering analysis, and scanning electron microscopy with energy dispersive X-ray spectroscopy. The catalyst could be reused six times without significant loss in activity. Furthermore, no chromatographic separations were needed to obtain the desired products.
- Kalla, Reddi Mohan Naidu,Lim, Jaehwa,Bae, Jaeyeong,Kim, Il
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supporting information
p. 1595 - 1599
(2017/04/03)
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- Carbon Tetrabromide/Triphenylphosphine-Activated Beckmann Rearrangement of Ketoximes for Synthesis of Amides
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An efficient Beckmann rearrangement of ketoximes was developed using carbon tetrabromide/triphenylphosphine as an organocatalyst without addition of any acids or metals. The reaction showed good functional group tolerance and gave various amides in moderate to good yields.
- Gao, Peng,Bai, Zijing
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supporting information
p. 1673 - 1677
(2017/10/05)
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