- Octamolybdate-based hybrids for direct conversion of aldehydes and ketones to oximes
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Two inorganic-organic hybrid materials, [Co(L)2]2Na2[β-Mo8O26]·9H2O (1) and [Fe(L)2]2Na2[β-Mo8O26]·9H2O (2) (HL = 2-acetylpyrazine N4-methyl thiosemicarbazone) have been synthesized and characterized by elemental analyses, infrared (IR) spectroscopy, thermal gravimetric analysis (TGA), powder X-ray diffraction (PXRD) and single-crystal X-ray diffraction. The hybrids 1 and 2 were explored in the oximation of aldehydes and ketones with in situ generated hydroxylamine by a one-pot procedure. In the crystal structures of 1 and 2, N-containing thiosemicarbazide ligands, Lewis acid, and oxidation catalyst octamolybdate coexist within a confined space providing a promising synergistic catalytic way. Hybrids 1 and 2 displayed high catalytic activity and selectivity for the oximation of aldehydes and ketones.
- Han, Pei Pei,Li, Jie,Xing, Cui Li,Zhao, Meng,Han, Qiu Xia,Li, Ming Xue
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- Kinetic Investigation of Micellar Promoted Pyridine based Oximate and Hydroxamate Catalysis on Phosphotriester Pesticides
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Abstract: The nucleophilic hydrolysis of paraoxon, parathion and fenitrothion by pyridine oximate (PyOx?) and hydroxamate (PyHA?) has been studied in aqueous and cationic micellar media. A noticeable kinetic changes has been observed at pH > pKadue to effective nucleophilicity of oximate (–CH=NO?) and hydroxamate (–CONHO?) functions. The Ox?nucleophile shows large reactivity than corresponding HA?. The reactivity of nucleophiles toward the electrophilic center of P=O and P=S bond of phosphate ester shows prominent effect in the presence of cetyltrimethylammonium bromide (CTAB) and tetradecyltrimethylammonium bromide (TTAB) micelles than aqueous media. The adjacent lone pair of electron in nitrogen atom on the nucleophile moiety of 2-PyOx and 2-PyHA helps to augment the reactivity compared to presence in remote of 4-PyOx and 4-PyHA nucleophile. The application of the pseudophase model of micellar catalysis showed that the ratio k2m/k2wis higher for the reaction of esters. Graphical Abstract: [Figure not available: see fulltext.]
- Dewangan, Hitesh K.,Nagwanshi, Rekha,Ghosh, Kallol K.,Satnami, Manmohan L.
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- Catalytic performance of a square planar nickel complex for electrochemical‐ and photochemical‐driven hydrogen evolution from water
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A square planar nickel complex bearing salicylketoxime (SAO), Ni-SAO has been synthesized and well characterized by ESI-MS and single-crystal X-ray diffraction, etc. Ni-SAO exhibits good activity in both electrocatalytic and photocatalytic hydrogen evolution reaction (HER). Under an overpotential (OP) of 837.6 mV, Ni-SAO can electrocatalyze hydrogen evolution from a neutral aqueous buffer with a turnover frequency (TOF) of 1428 mol of hydrogen per mole of catalyst per hour (mol H2 /mol catalyst/h). Moreover, under blue light (λ = 469 nm), a three-component system containing Ni-SAO as a catalyst, CdS nanorods (CdS NRs) as a photosensitizer, and ascorbic acid (H2A) as a sacrificial electron donor also can afford hydrogen with a turnover number (TON) of 8138 mol H2 per mol of catalyst (mol of cat?1) during 48 h irradiation. The highest apparent quantum yield (AQY) is about 16.5% at 469 nm.
- Du, Juan,Wang, Chun-Li,Yang, Hao,Zhan, Shu-Zhong
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- A self-assembled octanuclear complex bearing the uncommon close-packed {Fe4Mn4(μ4-O)4(μ-O)4} molecular core
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A one-pot open-air reaction of manganese powder with iron(ii) chloride in DMF solution of the Schiff base (H2L) formed in situ from salicylaldehyde and hydroxylamine hydrochloride yields the heterometallic complex [Fe4(μ4-O)4Mn4(L)8(DMF)4]·2DMF (1). Single crystal X-ray analysis shows that its molecular structure is based on the octanuclear core {Fe4Mn4(μ4-O)4(μ-O)4} with a quite rare molecular structure type {M8(μ4-X)4(μ-X)4}, where the central cube-like iron motif is modified with four terminal manganese fragments, the whole core being presented as the {Fe4(μ4-O)4} + 4{Mn(μ-O)} combination. Using the data from the Cambridge Structural Database (CSD), an analysis of the octanuclear structures with similar central {M4(μ4-X)4} fragments was performed. The hierarchical order of molecular structure types with the general formula M8Xn for such compounds was proposed and the topological features as well as the factors that influence the molecular type formation are discussed. Variable-temperature (1.8-300 K) magnetic susceptibility measurements reveal an antiferromagnetic coupling among the magnetic centres in 1.
- Nesterova, Oksana V.,Chygorin, Eduard N.,Kokozay, Vladimir N.,Omelchenko, Irina V.,Shishkin, Oleg V.,Boa, Roman,Pombeiro, Armando J. L.
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- Photophysical properties of a boron analogue of coumarin
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In this report, we present a study into the structure and electronic properties of difluoroboronsalicylaldoxime (DFBS), a boron-based structural analog of coumarin. The modification of the heterocyclic ring of coumarin with boron results in a compound with similar structural parameters and molecular orbitals to coumarin. DFT and TDDFT calculations reveal a significant stabilization of the LUMO in DFBS; this is supported by a ～40 nm red shift of the lowest electronic transition in the absorption spectrum. Interestingly, DFBS is emissive, while unmodified coumarin is effectively non-radiative. Comparisons between DFBS, emissive coumarin variants, and unmodified coumarin suggest that the charge transfer character of the transition contributes to the fluorescence. This journal is
- Schrage, Briana R.,Takematsu, Kana,Wang, Huayi,Ziegler, Christopher J.
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- Method for preparing 2-hydroxy-benzonitril by adopting micro-flow field technology
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The invention discloses a method for preparing 2-hydroxy benzonitrile (o-hydroxy benzonitrile) by adopting a micro-flow field technology, which comprises the following steps: (1) dissolving hydroxylamine hydrochloride in a solvent, adding salicylaldehyde, and fully stirring and uniformly mixing to obtain a reaction solution; and (2) pumping the uniformly mixed reaction liquid into the micro-channel reactor by adopting single-strand feeding, and carrying out one-step reaction to obtain a 2-hydroxy-benzonitrile crude product. Compared with a traditional preparation method of the 2-hydroxy-benzonitrile, the method has the advantages that the use of a dehydrating agent is avoided, the reaction time is short, the conversion rate of the 2-hydroxy-benzonitrile is high, the operation is simple, the safety is high, and the method is suitable for industrial production.
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Paragraph 0022; 0045-0047
(2021/08/14)
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- Poly(N-vinylimidazole): A biocompatible and biodegradable functional polymer, metal-free, and highly recyclable heterogeneous catalyst for the mechanochemical synthesis of oximes
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The catalytic activity of poly(N-vinylimidazole), a biocompatible and biodegradable synthetic functional polymer, was investigated for the synthesis of oximes as an efficient, halogen-free, and reusable heterogeneous catalyst. The corresponding oximes were afforded in high to excellent yields at room temperature and in short times using the planetary ball mill technique. Some merits, such as the short reaction times and good yields for poorly active carbonyl compounds, and avoiding toxic, expensive, metal-containing catalysts, and hazardous and flammable solvents, can be mentioned for the current catalytic synthesis of the oximes. Furthermore, the heterogeneous organocatalyst could be easily separated after the reaction, and the regenerated catalyst was reused several times with no significant loss of its catalytic activity.
- Fahim, Hoda,Ghaffari Khaligh, Nader,Gorjian, Hayedeh
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p. 2007 - 2012
(2022/01/08)
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- METHODS OF FORMING IMINES, IMINE-RELATED AND IMINE-DERIVED COMPOUNDS USING GREEN SOLVENTS
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The present disclosure relates to using green solvents to synthesize an array of imines, imine-related and imine-derived compounds in an efficient and eco-friendly matter, satisfying green chemistry requirements. Reaction embodiments are performed using solvents, such as ethyl lactate and dimethyl isosorbide, which are both individually characterized as green. In embodiments, solvents include lactic whey and/or water as co-solvents. In these green solvents, the synthesis process discussed herein can produce up to quantitative yields of product at room temperature in a short duration. Embodiments include a method of forming an imine, imine-related or imine-derived compound product. In embodiments, the methods include mixing an aldehyde reactant with a nucleophilic/nitrogen-containing reactant in a green solvent at a temperature between negative twenty degrees Celsius (?20° C.) and positive fifty degrees Celsius (50° C.); stirring the mixture; and forming an imine, imine-related or imine-derived compound product.
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Paragraph 0180-0183
(2021/10/22)
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- Method for improving conversion rate of azoxystrobin
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The invention discloses a method for improving the conversion rate of azoxystrobin. The method comprises the following steps: preparing methyl (E)-2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy acrylate; preparing o-hydroxybenzonitrile; mixing methyl (E)-2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy acrylate, o-hydroxybenzonitrile, potassium carbonate and ketene chloride according to a molar ratio of 30: 35: 50: 1.1, and dissolving the obtained mixture in dimethylformamide to obtain a mixed product; and heating the prepared mixed product, keeping the mixed product at a certain temperature, conducting filtering, carrying out reduced-pressure distillation, performing cooling, separating out crystals, carrying out filtering and washing and performing drying to obtain azoxystrobin. On the basis of the prior art, the synthesis of azoxystrobin is improved in the invention, so the yield of azoxystrobin is effectively increased, the conversion rate of the raw materials including methyl(E)-2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy acrylate and o-hydroxybenzonitrile for azoxystrobin in the process of preparing azoxystrobin is effectively improved, and the production benefit of azoxystrobin is improved.
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Paragraph 0066-0069
(2021/03/31)
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- AN IMPROVED PROCESS FOR PREPARATION OF PURE ALDOXIME
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The present invention relates to an improved process for preparing aldoximes of formula (I) with high purity and high yield. The improved process for preparing aldoxime is fast, simple, highly efficient, and reproducible. The improved process for the preparation of aldoxime, which is synthesized in the higher yield under oximation reaction of aldehyde with hydroxylamine hydrochloride merely in aqueous medium using of in situ heat generation.
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Page/Page column 18
(2021/06/22)
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- Preparation method O - alkyl substituted hydroxylamine salt
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The invention relates to a preparation method of N - alkyl substituted hydroxylamine salt, and belongs to fine chemical engineering. Pesticide or bulk pharmaceutical chemicals technical field. The present invention reacts with the N - alkyl of the oxime with an inorganic salt of hydroxylamine to give N - alkyl-substituted hydroxylamine salt and oxime. The invention provides an efficient and environment-friendly method for preparing N - alkyl substituted hydroxylamine salt, and simultaneously, an N - alkyl substituted hydroxylamine salt is prepared, and the oxime can be re-prepared to form N - alkylate of oxime so as to realize the material circulation. No equivalent acid is used in the reaction process. Alkali neutralization, avoided the current method to use a large amount of acid, alkali and produce inorganic salt solid waste shortcoming, environmental protection more. The preparation method is mild in reaction condition, and the defects of high pollution and high energy consumption of the traditional process are overcome. In-flight R1 , R2 What is R is as claimed in the claims and the description.
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Paragraph 0098; 0104-0107
(2021/11/14)
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- A Synergic Activity of Urea/Butyl Imidazolium Ionic Liquid Supported on UiO-66-NH2 Metal–Organic Framework for Synthesis of Oximes
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An efficient supported ionic liquid catalyst is designed for condensation reaction of aldehydes and ketones. The Zr-based metal–organic framework (MOF), UiO-66-NH2, was initially functionalized with N,N′-dibutyl imidazolium ionic liquid (UiO-66-NH2-ILBr–), and then urea was attached to the ionic liquid (IL) to form a task-specific IL. Bromide was exchanged with tetrafluoroborate and the catalyst exhibits excellent performance for the synthesis of oximes. The ionic liquid/urea coupling showed a synergistic effect on the efficiency of the reaction. The supported catalyst system was recycled simply by filtration and reused for five times without significant decrease in its activity. The catalyst was characterized with PXRD, FTIR, TGA, XPS, BET, FE-SEM, EDS, elemental mapping and elemental analysis (CHN). Graphic Abstract: MOF/IL/urea catalytic system was used for the synthesis of oximes[Figure not available: see fulltext.].
- Askari, Saeed,Jafarzadeh, Mohammad,Christensen, David Benjamin,Kegn?s, S?ren
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p. 3159 - 3173
(2020/04/21)
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- Adhesive functionalized ascorbic acid on CoFe2O4: A core-shell nanomagnetic heterostructure for the synthesis of aldoximes and amines
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This paper reports on the simple synthesis of novel green magnetic nanoparticles (MNPs) with effective catalytic properties and reusability. These heterogeneous nanocatalysts were prepared by the anchoring of Co and V on the surface of CoFe2O4 nanoparticles coated with ascorbic acid (AA) as a green linker. The prepared nanocatalysts have been identified by scanning electron microscopy, transmission electron microscopy, energy-dispersive X-ray spectroscopy, X-ray atomic mapping, thermogravimetric analysis, X-ray powder diffraction, vibrating sample magnetometer analysis, coupled plasma optical emission spectrometry and Fourier transform infrared spectroscopy. The impact of CoFe2O4@AA-M (Co, V) was carefully examined for NH2OH·HCl oximation of aldehyde derivatives first and then for the reduction of diverse nitro compounds with sodium borohydride (NaBH4) to the corresponding amines under green conditions. The catalytic efficiency of magnetic CoFe2O4@AA-M (Co, V) nanocatalysts was investigated in production of different aldoximes and amines with high turnover numbers (TON) and turnover frequencies (TOF) through oximation and reduction reactions respectively. Furthermore, the developed environment-friendly method offers a number of advantages such as high turnover frequency, mild reaction conditions, high activity, simple procedure, low cost and easy isolation of the products from the reaction mixture by an external magnetic field and the catalyst can be reused for several consecutive runs without any remarkable decrease in catalytic efficiency.
- Sorkhabi, Serve,Ghadermazi, Mohammad,Mozafari, Roya
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p. 41336 - 41352
(2020/11/30)
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- Synthesis and SAR study of simple aryl oximes and nitrofuranyl derivatives with potent activity against Mycobacterium tuberculosis
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Background: Oximes and nitrofuranyl derivatives are particularly important compounds in medicinal chemistry. Thus, many researchers have been reported to possess antibacterial, antiparasitic, insecticidal and fungicidal activities. Methods: In this work, we report the synthesis and the biological activity against Mycobacterium tuberculosis H37RV of a series of fifty aryl oximes, ArCH=N-OH, I, and eight nitrofuranyl compounds, 2-nitrofuranyl-X, II. Results: Among the oximes, I: Ar = 2-OH-4-OH, 42, and I: Ar = 5-nitrofuranyl, 46, possessed the best activity at 3.74 and 32.0 μM, respectively. Also, 46, the nitrofuran compounds, II; X = MeO, 55, and II: X = NHCH2Ph, 58, (14.6 and 12.6 μM, respectively), exhibited excellent biological activities and were non-cytotoxic. Conclusion: The compound 55 showed a selectivity index of 9.85. Further antibacterial tests were performed with compound 55 which was inactive against Enterococcus faecalis, Klebisiella pneumonae, Pseudomonas aeruginosa, Staphylococcus aureus, Salmonella typhymurium and Shigel-la flexneri. This study adds important information to the rational design of new lead anti-TB drugs. Structure-activity Relationship (SAR) is reported.
- Calixto, Stephane Lima,Carvalho, Guilherme da Silva Louren?o,Coimbra, Elaine Soares,Granato, Juliana da Trindade,Louren?o, Maria Cristina da Silva,Wardell, James,da Costa, Cristiane Fran?a,de Souza, Marcus Vinicius Nora
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- Chlorotropylium Promoted Conversions of Oximes to Amides and Nitriles
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Chlorotropylium chloride as a catalyst for the transformations of oximes, ketones, and aldehydes to their corresponding amides and nitriles in excellent yields (up to 99 %) and in short reaction times (mostly 10–15 min). Oximes were electrophilically attacked on the hydroxyl oxygen by chlorotropylium. The produced tropylium oxime ethers were the key intermediates, of which the ketoxime ether led to amide through Beckmann rearrangement, and the aldoxime ether led to nitrile by nitrogen base DBU assisted formal dehydration. This chlorotropylium activation protocol offered general, mild, and efficient avenues bifurcately from oximes to both amides and nitriles by one organocatalyst.
- Xu, Jiaxi,Gao, Yu,Li, Zhenjiang,Liu, Jingjing,Guo, Tianfo,Zhang, Lei,Wang, Haixin,Zhang, Zhihao,Guo, Kai
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p. 311 - 315
(2020/01/25)
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- High-Throughput Screening of the Alkoxide/Oxime-Based Library: An Alternative to Organotin Compounds for the Alkoxysilane Condensation in Adhesives and Sealants
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In this work, a high-throughput screening (HTS) method was used to discover new efficient catalysts to substitute organotin compounds (DBTDL) for the cross-linking of silyl-modified polymers (SMPs). We report here on the use of our HTS method to investigate a library of alkoxide/oxime systems with different metal/ligand (M/L) ratios. Among the 156 candidates tested, 40 interesting hits were detected. Then, the cross-linking times for the better hits were measured on the SMP. Some of these seem to be more efficient than DBTDL and exhibit a good stability during storage in cartridges. Thereby, a high efficiency of alkoxide/oxime systems was established that shows great potential for the generation of new ligands to provide new tin-free catalysts for the cross-linking of adhesives and sealants.
- Colin, Boris,Lavastre, Olivier,Fouquay, Stéphane,Michaud, Guillaume,Simon, Frédéric,Brusson, Jean-Michel
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supporting information
p. 300 - 309
(2019/02/19)
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- Synthesis and in vitro evaluation of neutral aryloximes as reactivators of Electrophorus eel acetylcholinesterase inhibited by NEMP, a VX surrogate
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Casualties caused by nerve agents, potent acetylcholinesterase inhibitors, have attracted attention from media recently. Poisoning with these chemicals may be fatal if not correctly addressed. Therefore, research on novel antidotes is clearly warranted. Pyridinium oximes are the only clinically available compounds, but poor penetration into the blood-brain barrier hampers efficient enzyme reactivation at the central nervous system. In searching for structural factors that may be explored in SAR studies, we synthesized and evaluated neutral aryloximes as reactivators for acetylcholinesterase inhibited by NEMP, a VX surrogate. Although few tested compounds reached comparable reactivation results with clinical standards, they may be considered as leads for further optimization.
- Cavalcante, Samir F. de A.,Kitagawa, Daniel A.S.,Rodrigues, Rafael B.,Bernardo, Leandro B.,da Silva, Thiago N.,dos Santos, Wellington V.,Correa, Ana Beatriz de A.,de Almeida, Joyce S.F.D.,Fran?a, Tanos C.C.,Ku?a, Kamil,Simas, Alessandro B.C.
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- Fe3O4@SiO2@Im[Cl]Mn(III)-complex as a highly efficient magnetically recoverable nanocatalyst for selective oxidation of alcohol to imine and oxime
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An efficient and environmentally friendly oxidation process for the one-pot preparation of oxime, imine and carbonyl compounds through alcohol oxidation in the presence of H2O2 and/or O2 have been developed by a melamine-Mn(III) Schiff base complex supported on Fe3O4@SiO2–Cl nanoparticles, named as Fe3O4@SiO2@Im[Cl]Mn(III)-complex nanocomposite, at room temperature. Direct oxidation of alcohol to carboxylic acid was performed using the catalyst in the presence of molecular O2 at room temperature in a different approach. The oxidation products were obtained with excellent yields and high TOFs. The properties of the catalyst were characterized by Fourier transform infrared spectroscopy (FTIR), elemental analysis (C, H, N), X-ray diffraction (XRD), field emission scanning electron microscopy (FE-SEM), dynamic light scattering (DLS), energy dispersive X-ray analysis (EDX), X-ray photoelectron spectroscopy (XPS), inductive coupled plasma (ICP), cyclic voltammetry (CV), nuclear magnetic resonance (1H & 13C NMR), vibration sample magnetometer (VSM), Brunauer– Emmett–Teller (BET) and differential pulse voltammetry (DPV) analyses. The mechanism of the oxidation processes was investigated for the both H2O2 and O2 oxidants. The role of the imidazolium moiety in the catalyst as a secondary functionality was investigated. Chemoselectivity behavior of the catalyst was studied by some combinations. The catalyst could be recycled from the reaction mixture by a simple external magnet and reused for several times without any considerable reactivity loss.
- Kazemnejadi, Milad,Alavi, Seyyedeh Ameneh,Rezazadeh, Zinat,Nasseri, Mohammad Ali,Allahresani, Ali,Esmaeilpour, Mohsen
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p. 230 - 249
(2019/03/28)
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- Synthesis and cytotoxic evaluation of undecenoic acid-based oxime esters
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A series of undecenoic acid-based aldoxime esters have been synthesized using various substituted benzaldehydes and undecenoic acid. These oxime esters have been evaluated for their cytotoxic activities against HeLa, B16-F10, SKOV3, MCF7 and CHO-K1 normal cell line using MTT assay. Most of the synthesized compounds exhibit cytotoxicity. Particularly, 2,3-dimethoxy (IC50 value 12.48μM) and 3-methoxy (IC50 value 13.58μM) derivatives exhibit promising activities against SKOV3 cell lines. All the synthesized compounds are non-toxic towards the Chinese hamster ovary (CHO-K1) normal cell line.
- Vijayendar, Venepally,Kaki, Shiva Shanker,Vamshi Krishna,Misra, Sunil,Prasad,Jala, Ram Chandra Reddy
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p. 1015 - 1022
(2019/05/22)
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- Novel design of recyclable copper(II) complex supported on magnetic nanoparticles as active catalyst for Beckmann rearrangement in poly(ethylene glycol)
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Copper complex-functionalized magnetic core–shell nanoparticles (Fe3O4@SiO2-Lig-Cu) were prepared and characterized using various techniques. The activity of the new catalyst was tested for the Beckmann rearrangement. The reaction conditions allow for the conversion of a wide variety of aldoximes, including aromatic and heterocyclic ones, to amides in good to excellent yields. High efficiency, mild reaction conditions, easy work-up, use of poly(ethylene glycol) as a green medium and simple purification of products are important advantages of this system. Moreover, the eco-friendly heterogeneous nanocatalyst could be easily recovered from the reaction mixture using an external magnet and reused several times.
- Keyhaniyan, Mahdi,Shiri, Ali,Eshghi, Hossein,Khojastehnezhad, Amir
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- Calculation and experimental measurement of paramagnetic NMR parameters of phenolic oximate Cu(II) complexes
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We present a strategy for predicting the unusual 1H and 13C shifts in NMR spectra of paramagnetic bisoximato copper(ii) complexes using DFT. We demonstrate good agreement with experimental measurements, although 1H-13C correlation spectra show that a combined experimental and theoretical approach remains necessary for full assignment.
- Dawson, Daniel M.,Ke, Zhipeng,Mack, Frederick M.,Doyle, Rachel A.,Bignami, Giulia P. M.,Smellie, Iain A.,Bühl, Michael,Ashbrook, Sharon E.
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supporting information
p. 10512 - 10515
(2017/09/29)
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- Poly(ethylene glycol)–bound sulfonyl chloride as an efficient catalyst for transformation of aldoximes to nitriles
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An operationally simple, efficient, and environmentally benign preparation of nitriles in good to excellent yields from various aldoximes in the presence of recyclable poly(ethylene glycol)–bound sulfonyl chloride is described.
- Zhang, Xiao-Lan,Liu, Xiao-Ling,Sang, Xiao-Yan,Sheng, Shou-Ri
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p. 232 - 237
(2017/01/22)
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- Synthesis and biological evaluation of (3-arylisoxazol-5-yl)methyl 6-fluoro-4-oxo-4H-chromene-2-carboxylates as antioxidant and antimicrobial agents
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A series of novel (3-arylisoxazol-5-yl)methyl 6-fluoro-4-oxo-4H- -chromene-2-carboxylate derivatives (C1-C12) were synthesized by the Cu(I)- -catalyzed reaction of in situ generated nitrile oxides with prop-2-ynyl 6-fluoro- 4-oxo-4H-chromene-2-carboxylate in good yields and their antioxidant and antimicrobial activities were investigated. Among all the synthesized compounds, C1 (IC50: 16.43±0.57 μM) and C12 (IC50:15.98±0.72 μM) registered good antioxidant activity as compared to the standard drug trolox. Compounds C1, C3 and C6 registered very good inhibition against all the tested Gram-positive and Gram-negative bacterial strains with MIC values ranging from 9.375 to 37.5 μg mL-1. Compounds C7-C11 registered good inhibition against Bacillus subtilis and Staphylococcus aureus with MIC values ranging from 18.75 to 37.5 μg mL-1. Compounds C10 and C11 against Pseudomonas aeroginosa showed more prominent activity than the standard drug penicillin (MIC: 12.5 μg mL-1) with an MIC value of 9.375 μg mL-1 (≈ 1.33-fold more potent than penicillin). Compounds C7-C9 registered good to moderate antifungal activity against the four tested fungal strains with MIC values ranging from 18.75 to 37.5 μg mL-1.
- Battula, Kumaraswamy,Narsimha, Sirassu,Nagavelli, Vasudeva Reddy,Rao, Mutheneni Srinivasa
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- Iron-catalyzed synthesis of benzoxazoles by oxidative coupling/cyclization of phenol derivatives with benzoyl aldehyde oximes
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An iron-catalyzed oxidative coupling/cyclization reaction for the synthesis of benzoxazoles at room temperature is reported. This reaction was enabled by an inexpensive iron(iii) catalyst by treating readily available phenol derivatives with benzoyl aldehyde oximes. Mechanistic studies show that benzoyl aldehyde oxime is not only used as a substrate, but also serves as an ancillary ligand to support the iron salt in the promotion of the transformation.
- Gao, Sen,Gao, Liming,Meng, Hong,Luo, Meiming,Zeng, Xiaoming
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supporting information
p. 9886 - 9889
(2017/09/11)
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- Synthesis and molecular modeling studies of N-Hydroxyindazolecarboximidamides as novel indoleamine 2,3-Dioxygenase 1 (IDO1) inhibitors
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Indoleamine 2,3-dioxygenase 1 (IDO1) is an immunosuppressive enzyme that is highly overexpressed in various cancer cells and antigen-presenting cells. It has emerged as an attractive therapeutic target for cancer immunotherapy, which has prompted high interest in the development of small-molecule inhibitors. To discover novel IDO1 inhibitors, we designed and synthesized a series of N-hydroxyindazolecarboximidamides. Among the compounds synthesized, compound 8a inhibited both tryptophan depletion and kynurenine production through the IDO1 enzyme. Molecular docking studies revealed that 8a binds to IDO1 with the same binding mode as the analog, epacadostat (INCB24360). Here, we report the synthesis and biological evaluation of these hydroxyindazolecarboximidamides and present the molecular docking study of 8a with IDO1.
- Lee, Dong-Ho,Lee, Joo-Youn,Jeong, Jieun,Kim, Miok,Lee, Kyung Won,Jang, Eunseo,Ahn, Sunjoo,Lee, Chang Hoon,Hwang, Jong Yeon
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- Direct preparation of oximes and Schiff bases by oxidation of primary benzylic or allylic alcohols in the presence of primary amines using Mn(III) complex of polysalicylaldehyde as an efficient and selective heterogeneous catalyst by molecular oxygen
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The present work introduced the new strategy for direct preparation of Schiff base as well as oxime compounds through oxidation of primary benzylic or allylic alcohols in the presence of amines by complexation of Mn(III) to a polymeric Schiff base ligand based on polysalicylaldehyde (PSA-Schiff base-Mn(III) complex). As a new environmentally benign protocol, manganese heterogeneous polymeric catalytic system demonstrated promising oxidation of alcohols in ethanol using molecular oxygen. PSA was synthesized through polycondensation reaction of 2-hydroxy-5-chloromethyl-benzaldehyde and then treated with 2-aminophenol to form polymeric ligand. Average molecular weight of PSA was studied by an analytical method as well as GPC analysis. Formation of the catalyst was characterized step by step by FTIR, UV–Vis, 1H NMR, TGA, CHN and EDX analyses. Loading amounts of metal ions as well as leaching amount of the catalysis were studied by ICP-OES instrument. The catalyst shows up to high yields for oxidation of primary and secondary primary benzylic or allylic alcohols to carbonyl compounds, especially direct imine formation in a mild, inexpensive and efficient method which can be successfully recovered from the reaction mixture and reused for several times without any remarkable reactivity loss. Effect of solvent, temperature, catalyst amount and oxygen donors along with some blank experiments to elucidation of catalyst activity was evaluated in this work. Also chemoselectivity behavior of the catalyst was investigated with some combinations.
- Kazemnejadi, Milad,Shakeri, Alireza,Mohammadi, Mohammad,Tabefam, Marzieh
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p. 1917 - 1933
(2017/08/15)
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- Five-membered azole heterocyclic compound and its preparation method, pharmaceutical composition and use thereof
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The present invention relates to a five-membered azole heterocycle compound represented by the following general formula (I), a preparation method of the five-membered azole heterocycle compound, a drug composition of the five-membered azole heterocycle compound, and a use of the five-membered azole heterocycle compound in preparation of drugs for prevention or treatment of TGR5-mediated diseases. The formula (I) is represented by the instruction.
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Paragraph 0378; 0379
(2017/02/28)
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- Paramagnetic NMR of Phenolic Oxime Copper Complexes: A Joint Experimental and Density Functional Study
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1H and13C pNMR properties of bis(salicylaldoximato)copper(II) were studied in the solid state using magic-angle-spinning NMR spectroscopy and, for the isolated complex and selected oligomers, using density-functional theory at the PBE0- 1/3//PBE0-D3 level. Large paramagnetic shifts are observed, up to δ(1H)=272 ppm and δ(13C)=1006 ppm (at 298 K), which are rationalised through spin delocalisation from the metal onto the organic ligand and the resulting contact shifts arising from hyperfine coupling. The observed shift ranges are best reproduced computationally using exchange-correlation functionals with a high fraction of exact exchange (such as PBE0- 1/3). Through a combination of experimental techniques and first-principles computation, a near-complete assignment of the observed signals is possible. Intermolecular effects on the pNMR shifts, modelled computationally in the dimers and trimers through effective decoupling between the local spins via A-tensor and total spin rescaling in the pNMR expression, are indicated to be small. Addition of electron-donating substituents and benzannelation of the organic ligand is predicted computationally to induce notable changes in the NMR signal pattern, which suggests that pNMR spectroscopy can be a sensitive probe for the spin distribution in paramagnetic phenolic oxime copper complexes.
- Bühl, Michael,Ashbrook, Sharon E.,Dawson, Daniel M.,Doyle, Rachel A.,Hrobárik, Peter,Kaupp, Martin,Smellie, Iain A.
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p. 15328 - 15339
(2016/10/13)
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- ZnO Nanotube as reusable catalyst in the efficient and selective oximation reaction of carbonyl groups under solvent free conditions
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A convenient and efficient procedure for the selective protection of carbonyl groups in the presence of ZnO nanotube, as reusable eco-friendly catalyst under solvent free conditions is described. The salient features of this methodology are cheaper process, easy availability of the catalyst, versatility, and the catalyst can be recovered after completion of the reaction and can be recycled without affecting the catalytic property.
- Kiasat, Ali Reza,Javaherian, Mohammad,Daei, Mina,Farbod, Mansoor
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p. 875 - 880
(2015/11/24)
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- AIEE active perylene bisimide supported mercury nanoparticles for synthesis of amides via aldoximes/ketoximes rearrangement
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Aggregates of perylene bisimide (PBI) derivative 3 serve as reactors and stabilizers for the preparation of mercury nanoparticles (HgNPs) which exhibit excellent catalytic efficiency in the conversion of aldoximes/ketoximes into primary/secondary amides via Beckmann rearrangement. This journal is
- Kaur, Sandeep,Kumar, Manoj,Bhalla, Vandana
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supporting information
p. 4085 - 4088
(2015/03/18)
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- Synthesis and cytotoxic activity evaluation of some novel 1-(3-(aryl-4,5-dihydroisoxazol-5-yl)methyl)-4-trihalomethyl-1H-pyrimidin-2-ones in human cancer cells
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Abstract The synthesis of a series of 14 new 1-(3-(aryl-4,5-dihydroisoxazol-5-yl)methyl)-4-trihalomethyl-1H-pyrimidin-2-ones from the 1,3-dipolar cycloaddition reaction of 1-allyl-4-(trihalomethyl)pyrimidin-2(1H)-ones with aryl nitrile oxides is described. Also, the antiproliferative activity of the title compounds was tested against five human tumoral cell lines: MCF-7 breast cancer cell line, ER+ (estrogen receptor positive); HepG-2 (hepatoma); T-24 (bladder cancer); HCT-116 cell (colorectal carcinoma); and CACO-2. The preliminary results are promising, since three compounds presented IC50 values below 2 μM, as well as moderate to high selectivity.
- Lobo, Marcio M.,Viau, Cassiana M.,Dos Santos, Josiane M.,Bonacorso, Helio G.,Martins, Marcos A.P.,Amaral, Simone S.,Saffi, Jenifer,Zanatta, Nilo
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p. 836 - 842
(2015/08/24)
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- Ruthenium Trichloride Catalyzed Highly Efficient Deoximation of Oximes to the Carbonyl Compounds and Nitriles without Acceptors
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An acceptor-free catalysis protocol for the deoximation of ketoximes and aldoximes using RuCl3 as the catalyst has been developed. Under the optimized conditions, various oximes were converted to ketones and nitriles with excellent isolated yields. An acceptor-free catalysis protocol for the deoximation of ketoximes and aldoximes using RuCl3 as the catalyst has been developed. Under the optimized conditions, various oximes were converted to ketones and nitriles with excellent isolated yields.
- Liu, Yuxiao,Yang, Na,Chu, Changhu,Liu, Renhua
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supporting information
p. 1011 - 1014
(2015/09/28)
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- Copper(ii)-promoted direct conversion of methylarenes into aromatic oximes
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A simple and efficient catalytic system for direct conversion of methylarenes into aromatic oximes has been developed, with Cu(OAc)2 as catalyst, NHPI (N-Hydroxyphthalimide) as additive, TBN (tert-butyl nitrite) as both the nitrogen source and the oxidant. This process proceeds under mild conditions, tolerates a wide range of substrates, affording the targeted aromatic oximes in 63-86% yields.
- Yu, Jiatao,Lu, Ming
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supporting information
p. 7397 - 7401
(2015/07/15)
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- Copper(II)-promoted direct conversion of methylarenes into aromatic oximes
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A simple and efficient catalytic system for direct conversion of methylarenes into aromatic oximes has been developed, with Cu(OAc)2 as catalyst, NHPI (N-Hydroxyphthalimide) as additive, TBN (tert-butyl nitrite) as both the nitrogen source and the oxidant. This process proceeds under mild conditions, tolerates a wide range of substrates, affording the targeted aromatic oximes in 63-86% yields.
- Yu, Jiatao,Lu, Ming
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supporting information
p. 7397 - 7401
(2015/11/27)
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- Novel and selective detection of Tabun mimics
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Detection of nerve agent-related molecules based on BODIPY-salicylaldehyde oxime conjugation was studied. Fluorescence intensity of the B-SAL-OXIME species increases in the presence of DECP, whereas it decreases in the presence of DCP and DEMP (limit of detection = 997 nM). Benzonitrile formation in the novel fluorescent B-SAL-OXIME system was elucidated using model substrates. the Partner Organisations 2014.
- Jang, Yoon Jeong,Tsay, Olga G.,Murale, Dhiraj P.,Jeong, Jeong A.,Segev, Aviv,Churchill, David G.
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supporting information
p. 7531 - 7534
(2014/07/07)
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- One-pot oximation-Beckmann rearrangement of ketones and aldehydes to amides of industrial interest: Acetanilide, caprolactam and acetaminophen
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High yielding one-pot oximation-Beckmann rearrangement of ketones to amides in ktrifluoroacetic acid has been conducted on several ketones and aldehydes. The substrate reactivity showed to depend on both oximation and Beckmann rearrangement reaction rate. In this synthetic procedure, trifluoroacetic acid acts as solvent, acid catalyst and organocatalyst and can be easily recycled.
- Aricò, Fabio,Quartarone, Giuseppe,Rancan, Elia,Ronchin, Lucio,Tundo, Pietro,Vavasori, Andrea
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- Green and highly selective protocol for the synthesis of oximes
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A green and efficient protocol has been developed for the synthesis of either exclusively a monoxime or exclusively a dioxime from a host of 1,2-dicarbonyl compounds on silica.
- Ghosh, Pranab,Subba, Raju
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p. 529 - 532
(2013/11/06)
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- Design, synthesis, and structure-activity relationships of 3,4,5-trisubstituted 4,5-dihydro-1,2,4-oxadiazoles as TGR5 agonists
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Given its role in the mediation of energy and glucose homeostasis, the G-protein-coupled bile acid receptor1 (TGR5) is considered a potential target for the treatment of type2 diabetes mellitus and other metabolic disorders. By thorough analysis of diverse structures of published TGR5 agonists, a hypothetical ligand-based pharmacophore model was built, and a new class of potent TGR5 agonists, based on the novel 3,4,5-trisubstituted 4,5-dihydro-1,2,4-oxadiazole core, was discovered by rational design. Three distinct synthetic methods for constructing 4,5-dihydro-1,2,4-oxadiazoles and extensive structure-activity relationship studies are reported herein. Compound (R)-54n, the structure of which was determined by single-crystal X-ray diffraction and quantum chemical solid-state TDDFT-ECD calculations, showed the best potency, with an EC50 value of 1.4nM toward hTGR5. Its favorable properties invitro warrant further investigation.
- Zhu, Junjie,Ye, Yangliang,Ning, Mengmeng,Mandi, Attila,Feng, Ying,Zou, Qingan,Kurtan, Tibor,Leng, Ying,Shen, Jianhua
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supporting information
p. 1210 - 1223
(2013/07/26)
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- On the stereochemistry of the olefinic double bond in 13-membered heterocyclic rings accessible by ring-closing metathesis reaction
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13-Membered heterocyclic ring analogs of the core structure of manzamine alkaloids were synthesized by ring closing metathesis (RCM) reaction. The influence of a remote heteroatom (N, O, S) on E/Z stereochemistry of the olefinic double bond formed in RCM reaction using Grubbs 1st and 2nd generation ruthenium carbene complexes was evaluated. Studies show that RCM reaction is kinetically controlled and the hetero atoms influence the double bond stereochemistry.
- Rao, H. Surya Prakash,Rafi, Shaik,Ratish Kumar,Guravaiah,Muthanna, Nandurka
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p. 6877 - 6880
(2013/01/15)
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- Efficient conversion of aldehydes and ketones into oximes using a nanostructured pyrophosphate catalyst in a solvent-free process
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A nanostructured pyrophosphate (Na2CaP2O7) was synthesized by controlling the speed of its calcination, and then characterized by several methods including TGA, X-ray diffraction, FTIR, SEM, TEM and the determination of the surface area by the BET method. However, several aldehydes and ketones were efficiently and rapidly converted into the corresponding oximes by treatment with hydroxylamine hydrochloride in a solvent-free process under microwave irradiation using this nanostructured pyrophosphate as catalyst. The yields of the products were very high and the time required for their preparation was very short compared to conventional heating experiments and the catalyst was efficiently re-used.
- Elmakssoudi, Abdelhakim,Abdelouahdi, Karima,Zahouily, Mohamed,Clark, James,Solhy, Abderrahim
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- A versatile and green mechanochemical route for aldehyde-oxime conversions
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A robust, facile and solvent-free mechanochemical path for aldehyde-oxime transformations using hydroxylamine and NaOH is explored; the method is suitable for aromatic and aliphatic aldehydes decorated with a range of substituents. This journal is
- Aakeroey, Christer B.,Sinha, Abhijeet S.,Epa, Kanishka N.,Spartz, Christine L.,Desper, John
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supporting information
p. 11289 - 11291,3
(2012/12/12)
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- Screening of ligands for the Ullmann synthesis of electron-rich diaryl ethers
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In the search for new ligands for the Ullmann diaryl ether synthesis, permitting the coupling of electron-rich aryl bromides at relatively low temperatures, 56 structurally diverse multidentate ligands were screened in a model system that uses copper iodide in acetonitrile with potassium phosphate as the base. The ligands differed largely in their performance, but no privileged structural class could be identified.
- Otto, Nicola,Opatz, Till
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supporting information; experimental part
p. 1105 - 1111
(2012/09/07)
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- Ruthenium-catalyzed rearrangement of aldoximes to primary amides in water
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The rearrangement of aldoximes to primary amides has been studied using the readily available arene-ruthenium(II) complex [RuCl2(η 6-C6Me6){P(NMe2)3}] (5 mol %) as catalyst. Reactions proceeded cleanly in pure water at 100 °C without the assistance of any cocatalyst, affording the desired amides in high yields (70-90%) after short reaction times (1-7 h). The process was operative with both aromatic, heteroaromatic, α,β-unsaturated, and aliphatic aldoximes and tolerated several functional groups. Reaction profiles and experiments using 18O-labeled water indicate that two different mechanisms are implicated in these transformations. In both of them, nitrile intermediates are initially formed by dehydration of the aldoximes. These intermediates are then hydrated to the corresponding amides by the action of a second molecule of aldoxime or water. A kinetic analysis of the rearrangement of benzaldoxime to benzamide is also discussed.
- Garcia-Alvarez, Rocio,Diaz-Alvarez, Alba E.,Borge, Javier,Crochet, Pascale,Cadierno, Victorio
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p. 6482 - 6490
(2012/10/30)
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- AMINOPYRAZINE COMPOUNDS USEFUL AS INHIBITORS OF TRA KINASE
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The present invention relates to compounds useful as inhibitors of ATR protein kinase. The invention also relates to pharmaceutically acceptable compositions comprising the compounds of this invention; methods of treating of various diseases, disorders, and conditions using the compounds of this invention; processes for preparing the compounds of this invention; intermediates for the preparation of the compounds of this invention; and methods of using the compounds in in vitro applications, such as the study of kinases in biological and pathological phenomena; the study of intracellular signal transduction pathways mediated by such kinases; and the comparative evaluation of new kinase inhibitors. The compounds of this invention have formula (I): wherein the variables are as defined herein.
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Page/Page column 96
(2012/10/18)
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- Efficient microwave-assisted synthesis of oximes from acetohydroxamic acid and carbonyl compounds using BF3·OEt2 as the catalyst
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An efficient synthesis of oximes by reaction of carbonyls with acetohydroxamic acid using BF3·OEt2 as a catalyst is described.
- Sridhar, Madabhushi,Narsaiah, Chinthala,Raveendra, Jillella,Kondal Reddy, Godala,Kishore Kumar Reddy, Mallu,China Ramanaiah, Beeram
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experimental part
p. 4701 - 4704
(2011/09/20)
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- Microwave-assisted efficient one-step synthesis of amides from ketones and benzoxazoles from (2-hydroxyaryl) ketones with acetohydroxamic acid using sulfuric acid as the catalyst
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Efficient one-step method for the synthesis of amides directly from ketones and benzoxazoles from (2-hydroxyaryl) ketones by the reaction of acetohydroxamic acid using sulfuric acid as catalyst was described.
- Madabhushi, Sridhar,Chinthala, Narsaiah,Vangipuram, Venkata Sairam,Godala, Kondal Reddy,Jillella, Raveendra,Mallu, Kishore Kumar Reddy,Beeram, China Ramanaiah
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experimental part
p. 6103 - 6107
(2011/11/30)
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- A rapid and convenient method for the synthesis of aldoximes under microwave irradiation using in situ generated ionic liquids
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We have developed a chemoselective, simple and efficient method for the preparation of aldoximes using microwave irradiation in the presence of tribenzylamine or 1,4-diazabicyclo[2.2.2]octane or 1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane bromide as bases and useful precursors for in situ generation of ionic liquids.
- Hajipour,Rafiee,Ruoho
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experimental part
p. 114 - 118
(2010/10/21)
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- Design and synthesis of novel isoxazole-based HDAC inhibitors
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A series of isoxazole-based histone deacetylase (HDAC) inhibitors structurally related to SAHA were designed and synthesized. The isoxazole moiety was inserted in the vicinity of the Zn2+-binding group in order to check its participation in the coordinating process. New isoxazole-based histone deacetylase inhibitors structurally related to SAHA were designed and synthesized to check the participation of the isoxazole moiety in the Zn 2+coordination.
- Conti, Paola,Tamborini, Lucia,Pinto, Andrea,Sola, Laura,Ettari, Roberta,Mercurio, Ciro,De Micheli, Carlo
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scheme or table
p. 4331 - 4338
(2010/09/16)
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- Synthesis and biological activity of 3-substituted isoxazolecarboxamides
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A series of novel 3-substituted isoxazolecarboxamides have been prepared. A key step was 1,3-dipolar cycloaddition of nitrile oxides to α,β-unsaturated esters. Some of these compounds exhibited high fungicidal activities against Alternaria alternata, Botrytis cinerea, Rhizoctonia solani, Fusarium culmorum, and Phytophthora cactorum.
- Gucma, Miroslaw,Golebiewski, W. Marek
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scheme or table
p. 461 - 469
(2011/07/30)
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- ZnO/CH3COCl: A new and highly efficient catalyst for dehydration of aldoximes into nitriles under solvent-free condition
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A rapid and efficient synthesis of nitriles via dehydration from the corresponding aldoximes has been carried out in the presence of ZnO/CH 3COCl as catalyst under solvent free conditions in 83-95% yields. The zinc oxide (ZnO) powder can be re-used upto three times after simple washing with CH2Cl2.
- Sarvari, Mona Hosseini
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p. 787 - 790
(2007/10/03)
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