22116-67-2Relevant academic research and scientific papers
Photoredox-Catalyzed Synthesis of α-Amino Acid Amides by Imine Carbamoylation
Cardinale, Luana,Schmotz, Mattis-Ole W. S.,Konev, Mikhail O.,Jacobi von Wangelin, Axel
supporting information, p. 506 - 510 (2022/01/20)
An operationally simple protocol for the photocatalytic carbamoylation of imines is reported. Easily available, bench-stable 4-amido Hantzsch ester derivatives serve as precursors to carbamoyl radicals that undergo rapid addition to N-aryl imines. The reaction proceeds under blue light irradiation in the presence of the photocatalyst 3DPAFIPN and Br?nsted/Lewis acid additives. Mechanistic studies indicated a photoredox mechanism that involves carbamoyl radicals.
CO2-Catalyzed Efficient Dehydrogenation of Amines with Detailed Mechanistic and Kinetic Studies
Riemer, Daniel,Schilling, Waldemar,Goetz, Anne,Zhang, Yu,Gehrke, Sascha,Tkach, Igor,Hollóczki, Oldamur,Das, Shoubhik
, p. 11679 - 11687 (2018/11/23)
CO2-catalyzed dehydrogenation of amines has been achieved under photocatalytic conditions. With this concept, various amines have been selectively dehydrogenated to the corresponding imines in the presence of different functional groups such as nitrile, nitro, ester, halogen, ether, thioether, and carbonyl or carboxylic acid moieties. At the end, the CO2-catalyzed synthesis of pharmaceutical drugs has been achieved. The CO2 radical has been detected by EPR spectroscopy using DMPO, and the mechanism of this reaction is proposed on the basis of DFT calculations and experimental evidence.
Direct synthesis of imines by 9-azabicyclo-[3,3,1]nonan-N-oxyl/KOH-catalyzed aerobic oxidative coupling of alcohols and amines
Wan, Yan,Ma, Jia-Qi,Hong, Chao,Li, Mei-Chao,Jin, Li-Qun,Hu, Xin-Quan,Hu, Bao-Xiang,Mo, Wei-Min,Sun, Nan,Shen, Zhen-Lu
, p. 1269 - 1272 (2017/10/26)
A simple and efficient method for preparation of imines by the oxidative coupling of benzyl alcohols with aromatic amines or aliphatic amines was developed. The reaction was catalyzed by 9-azabicyclo[3.3.1]nonan-N-oxyl (ABNO)/KOH with air as the economic and green oxidant. Under the optimal reaction conditions, a variety of imines were obtained in 80%-96% isolated yields.
Method for preparing imine compound from alcohol and amine through catalytic oxidation
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Paragraph 0043, (2017/08/31)
The invention discloses a method for preparing an imine compound from alcohol and amine through catalytic oxidation. According to the method, an alcohol compound and an amine compound are used as reaction substrates, and a feeding mol ratio of the alcohol compound to the amine compound is 100: 100-60; 9-azabicyclo[3.3.1]nonane N-oxyl free radical is used as a catalyst, potassium hydroxide is used as an auxiliary agent, and a feeding mol ratio of the amine compound to the 9-azabicyclo[3.3.1]nonane N-oxyl free radical to potassium hydroxide is 100: 1-6: 10-50; air is used as an oxidizing agent, the reaction substrates are added into an organic solvent, and the mass of the used organic solvent is 2.5 to 5 times of the reaction substrate the amine compound; and a reaction is carried out at normal pressure at a temperature of 70 to 110 DEG C for 2 to 12 h, and aftertreatment is carried out after completion of the reaction so as to obtain the imine compound. The method provided by the invention is simple and safe to operate, reduces environmental cost due to usage of clean oxygen as the oxidizing agent and prevents the problem of transition-metal pollution by discarding usage of any transition-metal catalyst.
General and selective reductive amination of carbonyl compounds using a core-shell structured Co3O4/NGr@C catalyst
Stemmler, Tobias,Westerhaus, Felix A.,Surkus, Annette-Enrica,Pohl, Marga-Martina,Junge, Kathrin,Beller, Matthias
, p. 4535 - 4540 (2014/12/10)
The application of heterogenized non-noble metal-based catalysts in selective catalytic hydrogenation processes is still challenging. In this respect, the preparation of a well-defined cobalt-based catalyst was investigated by immobilization of the corresponding cobalt(ii)-phenanthroline-chelate on Vulcan XC72R carbon powder. The formed core-shell structured cobalt/cobalt oxide nanocomposites are encapsulated by nitrogen-enriched graphene layers. This promising cheap heterogeneous catalyst allows for an efficient domino reductive amination of carbonyl compounds with nitroarenes. This journal is
Iron-catalyzed synthesis of secondary amines: On the way to green reductive aminations
Stemmler, Tobias,Surkus, Annette-Enrika,Pohl, Marga-Martina,Junge, Kathrin,Beller, Matthias
, p. 3012 - 3016 (2015/09/28)
Amines represent important intermediates in chemical and biological processes. Herein, we describe the use of a nanostructured iron-based catalyst for the tandem reductive amination between nitroarenes and aldehydes using hydrogen as reductant. The nanostructured iron-catalyst is prepared by immobilization of an iron-phenanthroline complex onto a commercially available carbon support. In the reaction sequence a primary amine is formed in situ from the corresponding nitro compound. Reversible condensation with aldehydes forms the respective imines, which are finally reduced to the desired secondary amine. This synthesis of secondary amines is atom-economical and environmentally attractive using cheap and readily available organic compounds as starting materials.
A molybdenum based metallomicellar catalyst for controlled and selective sulfoxidation reactions in aqueous medium
Chakravarthy, Rajan Deepan,Ramkumar, Venkatachalam,Chand, Dillip Kumar
, p. 2190 - 2196 (2014/04/17)
A surfactant based molybdenum system that exhibits catalytic activity for sulfoxidation reactions of various organic sulfides in aqueous medium has been developed and comprehensively characterized using IR, XRD, NMR, ESI-MS, DLS and TEM. The catalyst showcases remarkable selectivity for the preparation of both sulfoxides and sulfones in the range of good to excellent yields. Furthermore, the catalyst showed a high degree of tolerance towards various sensitive functional groups such as hydroxyl, acetal, aldehyde, amine, imine, oxime, cyano and alkene. the Partner Organisations 2014.
Analogue-based design, synthesis and docking of non-steroidal anti-inflammatory agents. Part 2: Methyl sulfanyl/methyl sulfonyl substituted 2,3-diaryl-2,3-dihydro-1H-quinazolin-4-ones
Manivannan,Chaturvedi
, p. 7119 - 7127 (2013/01/15)
A series of methyl sulfanyl/methyl sufonyl substituted 2,3-diaryl-2,3- dihydro-1H-quinazolin-4-one were designed using analogue-based design, scaffold hopping and shape similarity matching. The designed compounds were synthesized in 2-3 steps with simple chemistry and screened by ovine cyclooxygenases (COXs) inhibitory assay and carrageenan-induced rat paw edema assay. Among the screened compounds, two compounds exhibited 100% cyclooxygenase-2 (COX-2) inhibitory potency without showing cycloxygenase-1 (COX-1) inhibition at 20 μM. The compounds also showed promising in vivo anti-inflammatory potential. A structure-activity relationship within the dataset was established by correlating the effect of aromatic ring substituent constants, structural variables and physico-chemical descriptors with in vivo anti-inflammatory activity. Molecular docking studies were also performed on the title compounds to study the binding interactions to COX-2 active site residues. The experimentally determined COX-2 inhibitory activity was found moderately correlating with binding modes predicted for compounds by Glide XP dock scoring function. The 2,3-diaryl-2,3-dihydro-1H-quinazolin-4-one pharmacophore reported herein should be a new lead for further development of novel non-steroidal anti-inflammatory agents.
1,5-Diarylimidazoles with strong inhibitory activity against COX-2 catalyzed PGE2 production from LPS-induced RAW 264.7 cells
Che, Haiyan,Tuyen, Truong Ngoc,Kim, Hyun Pyo,Park, Haeil
body text, p. 4035 - 4037 (2010/08/06)
A series of 1,5-diarylimidazoles with 4-methylsulfonylphenyl group were prepared and evaluated for the inhibitory activities against COX-2 catalyzed PGE2 production from LPS-induced RAW 264.7 cells. Most of synthesized 1,5-diarylimidazoles exhibited strong inhibitory activities regardless of the position of the 4-methylsulfonylphenyl group. The 1,5-diarylimidazoles with a halogen atom (3c-3h, 3n-3p) gave mostly excellent inhibitory activities regardless of the position and species of the halogen atom. Whereas the 1,5-diarylimidazoles with two fluorine atoms (3k, 3l, 3r, 3s) showed rather reduced inhibitory activities.
