- Solvent-Dependent Oxime-Azide and Oxime-Nitrile Coupling: Crystallographic and Catalytic Studies
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This study describes the solvent-dependent conversion of an oxime under identical reaction conditions ([Cu(bipy)Cl2]/NaN3/5-Br-H2salox/TEA=1:2:1:2 molar ratio; bipy=2,2′-bipyridyl, 5-Br-H2salox=5-bromosalicylaldoxime, TEA=triethylamine), but in different solvents. In DMSO/CH2Cl2 (2:1v/v) only tetrazole is formed, whereas iminoacylation in MeCN and simple complexation takes place in MeOH. The formed tetrazole and iminoacylated ligands further undergo complexation with metal ions, as evidenced from single-crystal X-ray diffraction studies and ESI-MS analyses. Mechanistic models have been proposed in which coordination-assisted bonding of sodium azide across the -C=N-OH double bond occurs to form a tetrazole and oxime-MeCN coupling forms an iminoacylated ligand. The former is a catalytic reaction, as evidenced from a turnover number of approximately 50, whereas the latter is stoichiometric in nature. This is the first report to demonstrate the dependence of solvent polarity on oxime transformation reactions through structural elucidation.
- Dolai, Malay,Mistri, Tarun,Biswas, Surajit,Rogez, Guillaume,Ali, Mahammad
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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 0176-0179
(2021/10/22)
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- Compounds For The Treatment Of Neuromuscular Disorders
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The present invention relates to compounds suitable for treating, ameliorating and/or preventing neuromuscular disorders, including the reversal of drug-induced neuromuscular blockade. The compounds as defined herein preferably inhibit the ClC-1 ion chann
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Paragraph 1546-1547
(2019/07/03)
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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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- Preparation method for 4-substituted piperidine derivative
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The invention discloses a preparation method for a 4-substituted piperidine derivative, i.e., 4-((2-(aminomethyl)-4-bromophenoxyl)methyl)piperidine-1-t-butyl formate. According to the invention, 5-bromo-2-hydroxybenzaldehyde is used as a starting material and subjected to oximation, elimination, etherification and catalytic hydrogenation so as to prepare the target derivative. The prepared derivative is an important medical intermediate.
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Paragraph 0020-0022
(2017/07/19)
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- Method for preparing piperazine derivatives
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The invention discloses a method for preparing piperazine derivatives 4-((2-(cyanobenzylamine hydrochloride)-4-bromobenzene oxygroup) methyl) piperazine-1-tert-butyl formate. The piperazine derivatives are made of 5-bromine-2-hydroxybenzaldehyde which is used as a starting material. The method includes carrying out oximation, elimination, etherification and catalytic hydrogenation reaction to obtain target products. The method has the advantage that the piperazine derivatives which are chemical compounds are important pharmaceutical intermediates.
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Paragraph 0020-0022
(2017/08/30)
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- GLUCOSYLCERAMIDE SYNTHASE INHIBITORS FOR THE TREATMENT OF DISEASES
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Described herein are compounds of Formula I, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or conditions associated with the enzyme glucosylceramide synthase (GCS).
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Paragraph 0001053
(2015/04/15)
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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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- Heck cross-coupling for synthesizing metal-complexing monomers
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New polymerizable ligands for complexing metal ions have been synthesized. The polymerizable ligands were made by Heck cross-coupling of aromatic bromides with high pressure ethylene gas under mild conditions at room temperature. The vinyl substituted ligands were prepared in good yields and characterized by GC-MS, FT-NMR, FT-IR and microanalysis. Georg Thieme Verlag Stuttgart.
- Southard, Glen E.,Van Houten, Kelly A.,Murray, George M.
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p. 2475 - 2477
(2008/02/03)
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- NOVEL FLUORINATED DYE STABILIZERS IN FLUORINATED DIELECTRIC SOLVENT
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The present invention is directed to novel fluorinated dye stabilizers having both high quenching efficiency and solubility in halogenated solvents. These dye stabilizers have shown a significantly effect on improving the dye fastness in hostile photooxidation conditions.
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- Inhibition of monoamine oxidases by coumarin-3-acyl derivatives: Biological activity and computational study
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A series of coumarin-3-acyl derivatives have been synthesized and investigated for the ability to inhibit selectively monoamine oxidases. The coumarin-3-carboxylic acids, 2a-e, proved to be reversible and selective inhibitors of the MAO-B isoform, display
- Chimenti, Franco,Secci, Daniela,Bolasco, Adriana,Chimenti, Paola,Granese, Arianna,Befani, Olivia,Turini, Paola,Alcaro, Stefano,Ortuso, Francesco
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p. 3697 - 3703
(2007/10/03)
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- NMR spectral assignment of substituted salicylaldoximes by inverse pulse techniques with z-gradient selection: Correlation of NMR parameters with substituent constants
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1H and 13C and also 1H,13C HMQC and 1H,X HMBC (X = 13C and 15N) correlation maps with z-gradient selection of seven salicylaldoximes were recorded and assigned and their paramete
- Kolehmainen, Erkki,Gawinecki, Ryszard,O?mia?owski, Borys,Trzebiatowska, Katarzyna
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p. 778 - 784
(2007/10/03)
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