194044-54-7Relevant articles and documents
Application of (MWCNTs)-COOH/CeO2 hybrid as an efficient catalyst for the synthesis of some nitrogen-containing organic compounds
Heidarzadeh, Tahereh,Nami, Navabeh,Zareyee, Daryoush
, (2021/08/18)
ABSTRACT: Modification of acid functionalized multi-walled carbon nanotubes (MWCNTs)-COOH with CeO2 nanoparticles using Ce(NO3)2.6H2O, produced an efficient catalyst for the synthesis of some nitrogen-containing heterocycles such as celecoxib. The products were identified by CHN analysis, NMR, and FT-IR spectra. On the other hand, synthesis of CeO2 nanoparticles and their conjugation on the surface of (MWCNTs)-COOH have been confirmed by FT-IR, scanning electron microscopy (SEM), transmission electron microscopy (TEM), X-ray diffraction (XRD), and Energy-dispersive X-ray spectroscopy (EDX).
Nickel(II)-Catalyzed Addition of Aryl and Heteroaryl Boroxines to the Sulfinylamine Reagent TrNSO: The Catalytic Synthesis of Sulfinamides, Sulfonimidamides, and Primary Sulfonamides
Lo, Pui Kin Tony,Willis, Michael C.
, p. 15576 - 15581 (2021/10/02)
We report a redox-neutral Ni(II)-catalyzed addition of (hetero)aryl boroxines to N-sulfinyltritylamine (TrNSO). The reactions use a catalyst generated from the combination of commercial, air-stable NiCl2·(glyme) and a commercially available bipyridine lig
Rapid Access to N-Protected Sulfonimidoyl Fluorides: Divergent Synthesis of Sulfonamides and Sulfonimidamides
Liu, Yongan,Pan, Qijun,Hu, Xiaojun,Guo, Yong,Chen, Qing-Yun,Liu, Chao
, p. 3975 - 3980 (2021/05/26)
Herein we report a practical and efficient copper-catalyzed approach for the conversion of various arenediazonium salts to the corresponding N-protected sulfonimidoyl fluorides. This operationally simple protocol tolerates a wide range of functional groups and can be applied to the late-stage modification of complex bioactive molecules. Furthermore, pharmaceutically important primary sulfonamides and sulfonimidamides derived from these valuable N-protected sulfonimidoyl fluoride units were prepared in minimal synthetic steps.
Copper-Catalyzed Reductive Ring-Cleavage of Isoxazoles: Synthesis of Fluoroalkylated Enaminones and Application for the Preparation of Celecoxib, Deracoxib, and Mavacoxib
Wan, Chao,Pang, Jian-Yu,Jiang, Wei,Zhang, Xiao-Wei,Hu, Xiang-Guo
, p. 4557 - 4566 (2021/03/01)
We have identified a new reactivity of copper/diamine catalysis for the reductive ring-cleavage of isoxazoles to yield fluoroalkylated enaminones. This protocol has the advantage of using commercially available reagents, ease of setting up, broad tolerance of functionality, and is regiospecific and free of defluorination and reduction of reducible functional groups. The utility was demonstrated by a one-step, regioselective synthesis of fluoroalkylated pyrazole-based drugs such as celecoxib, deracoxib, and mavacoxib.
A CONTINUOUS FLOW MICRO-TOTAL PROCESS SYSTEM FOR PREPARATION OF CELECOXIB AND ANALOGS THEREOF
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Page/Page column 16-17, (2020/08/22)
The present invention relates to preparation of pyrazoles. This invention further relates to a continuous flow micro-total process system for preparation of celecoxib, a COX-2 selective non-steroidal anti-inflammatory drug, and analogs thereof.
Preparation method of celecoxib
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Paragraph 0014; 0021, (2020/07/13)
A preparation method of celecoxib comprises the following steps: preparing CEL-A completion liquid, preparing a crude dry celecoxib product, and purifying, drying and crushing the crude dry celecoxibproduct. The celecoxib product prepared by the method has the advantage of high purity.
Primary Sulfonamide Synthesis Using the Sulfinylamine Reagent N-Sulfinyl- O-(tert-butyl)hydroxylamine, t-BuONSO
Davies, Thomas Q.,Hall, Adrian,Skolc, David,Tilby, Michael J.,Willis, Michael C.
supporting information, p. 9495 - 9499 (2020/12/21)
Sulfonamides have played a defining role in the history of drug development and continue to be prevalent today. In particular, primary sulfonamides are common in marketed drugs. Here we describe the direct synthesis of these valuable compounds from organometallic reagents and a novel sulfinylamine reagent, t-BuONSO. A variety of (hetero)aryl and alkyl Grignard and organolithium reagents perform well in the reaction, providing primary sulfonamides in good to excellent yields in a convenient one-step process.
HFO-1234yf as a CF3-Building Block: Synthesis and Chemistry of CF3-Ynones
Murray, Ben J.,Marsh, Thomas G. F.,Yufit, Dmitri S.,Fox, Mark A.,Harsanyi, Antal,Boulton, Lee T.,Sandford, Graham
, p. 6236 - 6244 (2020/09/15)
Reaction of low cost, readily available 4th generation refrigerant gas 2,3,3,3-tetrafluoropropene (HFO-1234yf) with lithium diisopropylamide (LDA) leads to formation of lithium 3,3,3-trifluoropropynide, addition of which to a range of aldehydes formed CF3-alkynyl alcohol derivatives on multigram scale, which were oxidised using Dess–Martin periodinane (DMP) to give substituted CF3-ynones with minimal purification required. Michael-type additions of alcohol and amine nucleophiles to CF3-ynones are rapid and selective, affording a range of CF3-enone ethers and enaminones in excellent yields with high stereoselectivity for the Z-isomer. By analogous reactions with difunctional nucleophiles, a wide range of CF3-substituted pharmaceutically relevant heterocyclic structures can be accessed, exemplified in the simple synthesis of the anti-arthritis drug celecoxib from HFO-1234yf in just three steps.
One-Pot Synthesis of Indoles and Pyrazoles via Pd-Catalyzed Couplings/Cyclizations Enabled by Aqueous Micellar Catalysis
Akporji, Nnamdi,Braga, Felipe C.,Gabriel, Christopher M.,Landstrom, Evan B.,Lee, Nicholas R.,Lipshutz, Bruce H.
supporting information, (2020/09/02)
An effective one-pot synthesis of either indoles or pyrazoles can be achieved via Pd-catalyzed aminations followed by subsequent cyclizations facilitated by aqueous micellar catalysis. This new technology includes efficient couplings with low loadings of palladium, a more stable source of the required hydrazine moiety, greater atom economy for the initial coupling, and reduced reaction temperatures, all leading to environmentally responsible processes.
Preparation method of celecoxib
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Paragraph 0018-0025, (2020/06/20)
The invention provides an efficient preparation method of 4-[3-trifluoromethyl-5-(4-methylphenyl)-1H-pyrazolyl]benzenesulfonamide (celecoxib). The method comprises the following steps of: taking 1, 1,1-trifluoro-4-methylphenyl butenone as a raw material, adding dilute acid and 4-aminosulfonylphenylhydrazine hydrochloride into methanol and water, and performing heating to obtain celecoxib. The method has the characteristics of mild reaction conditions, simple operation, high product yield and purity, and few isomers, and is suitable for industrial production.
