50-49-7Relevant academic research and scientific papers
Simple RuCl3-catalyzed N-Methylation of Amines and Transfer Hydrogenation of Nitroarenes using Methanol
Sarki, Naina,Goyal, Vishakha,Tyagi, Nitin Kumar,Puttaswamy,Narani, Anand,Ray, Anjan,Natte, Kishore
, p. 1722 - 1729 (2021/04/19)
Methanol is a potential hydrogen source and C1 synthon, which finds interesting applications in both chemical synthesis and energy technologies. The effective utilization of this simple alcohol in organic synthesis is of central importance and attracts scientific interest. Herein, we report a clean and cost-competitive method with the use of methanol as both C1 synthon and H2 source for selective N-methylation of amines by employing relatively cheap RuCl3.xH2O as a ligand-free catalyst. This readily available catalyst tolerates various amines comprising electron-deficient and electron-donating groups and allows them to transform into corresponding N-methylated products in moderate to excellent yields. In addition, few marketed pharmaceutical agents (e. g., venlafaxine and imipramine) were also successfully synthesized via late-stage functionalization from readily available feedstock chemicals, highlighting synthetic value of this advanced N-methylation reaction. Using this platform, we also attempted tandem reactions with selected nitroarenes to convert them into corresponding N-methylated amines using MeOH under H2-free conditions including transfer hydrogenation of nitroarenes-to-anilines and prepared drug molecules (e. g., benzocaine and butamben) as well as key pharmaceutical intermediates. We further enable one-shot selective and green syntheses of 1-methylbenzimidazole using ortho-phenylenediamine (OPDA) and methanol as coupling partners.
A fluorine-containing methyl compounds and its preparation method (by machine translation)
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Paragraph 0179; 0180; 0185; 0186; 0187; 0188; 0338-0341, (2019/05/11)
The invention discloses a fluorine-containing methyl compounds and its preparation method. The invention provides a fluorine-containing shown as formula C methyl compounds, wherein R is aryl group containing, or, containing a hetero aryl group, and the aryl group or the heteroaryl on the aromatic carbon atom and CFm Hn Connected, m is 1 or 2, m + n=3. The compounds according to the prior art is difficult to make, the preparation method of the raw material and the catalyst are the ordinary industrial raw materials, cheap and easy to obtain, high reaction efficiency, high yield, after treatment is simple, low toxicity, environmental protection, functional group compatibility is good, broad-spectrum is strong, the production cost is low, it has very good market application prospect. (by machine translation)
A Focused Library of Psychotropic Analogues with Neuroprotective and Neuroregenerative Potential
Uliassi, Elisa,Pena-Altamira, Luis Emiliano,Morales, Aixa V.,Massenzio, Francesca,Petralla, Sabrina,Rossi, Michele,Roberti, Marinella,Martinez Gonzalez, Loreto,Martinez, Ana,Monti, Barbara,Bolognesi, Maria Laura
, p. 279 - 294 (2018/10/20)
Overcoming the lack of effective treatments and the continuous clinical trial failures in neurodegenerative drug discovery might require a shift from the prevailing paradigm targeting pathogenesis to the one targeting simultaneously neuroprotection and neuroregeneration. In the studies reported herein, we sought to identify small molecules that might exert neuroprotective and neuroregenerative potential as tools against neurodegenerative diseases. In doing so, we started from the reported neuroprotective/neuroregenerative mechanisms of psychotropic drugs featuring a tricyclic alkylamine scaffold. Thus, we designed a focused-chemical library of 36 entries aimed at exploring the structural requirements for efficient neuroprotective/neuroregenerative cellular activity, without the manifestation of toxicity. To this aim, we developed a synthetic protocol, which overcame the limited applicability of previously reported procedures. Next, we evaluated the synthesized compounds through a phenotypic screening pipeline, based on primary neuronal systems. Phenothiazine 2Bc showed improved neuroregenerative and neuroprotective properties with respect to reference drug desipramine (2Aa). Importantly, we have also shown that 2Bc outperformed currently available drugs in cell models of Alzheimer's and Parkinson's diseases and attenuates microglial activation by reducing iNOS expression.
Identification and Structural Characterization of Three New Metabolites of Bupropion in Humans
Sager, Jennifer E.,Choiniere, John R.,Chang, Justine,Stephenson-Famy, Alyssa,Nelson, Wendel L.,Isoherranen, Nina
supporting information, p. 791 - 796 (2016/08/24)
Bupropion is a widely used antidepressant and the recommended CYP2B6 probe drug. However, current understanding of bupropion elimination pathways is limited. Bupropion has three active circulating metabolites, OH-bupropion, threohydrobupropion, and erythrohydrobupropion, but together with bupropion these metabolites and their conjugates in urine represent only 23% of the dose, and the majority of the elimination pathways of bupropion result in uncharacterized metabolites. The aim of this study was to determine the structures of the uncharacterized bupropion metabolites using human clinical samples and in vitro incubations. Three new metabolites, 4′-OH-bupropion, erythro-4′-OH-hydrobupropion, and threo-4′-OH-hydrobupropion, were detected in human liver microsome incubations and were isolated from human urine. The structures of the metabolites were confirmed via comparison of UV absorbance, NMR spectra, and mass spectral data to those of the synthesized standards. In total, these metabolites represented 24% of the drug related material excreted in urine.
METHOD OF PREPARATION OF IMIPRAMINE PAMOATE AND NOVEL CRYSTALLINE FORM OF IMIPRAMINE PAMOATE THEREOF
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Paragraph 0034, (2015/09/22)
The present invention is in relation to preparation of Imipramine Pamoate by a simple two-step process. The process provides new form of Imipramine Pamoate. The present invention is cost effective, involves mild conditions to beget said compound.
Csp3-Csp3 homocoupling reaction of benzyl halides catalyzed by rhodium
Sato, Kazuyuki,Inoue, Yuichi,Mori, Tomohisa,Sakaue, Atsushi,Tarui, Atsushi,Omote, Masaaki,Kumadaki, Itsumaro,Ando, Akira
supporting information, p. 3756 - 3759 (2014/08/05)
A highly reactive alkylrhodium complex was formed from Me2Zn and RhCl(PPh3)3 and effectively catalyzed a Csp 3-Csp3 homocoupling reaction of benzyl halides. A Csp 3-Csp3 coupling reaction using Rh catalyst has not been reported up to now. The reaction proceeded under very mild conditions and gave the corresponding homocoupling products even if they had reactive substituents such as an uncovered formyl or hydroxymethyl group.
General catalytic methylation of amines with formic acid under mild reaction conditions
Sorribes, Ivan,Junge, Kathrin,Beller, Matthias
supporting information, p. 7879 - 7883 (2014/07/07)
A general catalytic protocol for the methylation of amines has been developed applying, for the first time, formic acid as the C1 building block and silanes as reducing agents. A broad range of aromatic and aliphatic, both primary and secondary, amines has been converted to the corresponding tertiary amines including [N-13C]-labelled drugs in good to excellent yields under mild conditions. Methylation made easy: A general catalytic protocol for the methylation of amines has been developed applying, for the first time, formic acid as the C1 building block and silanes as reducing agents. A broad range of aromatic and aliphatic, both primary and secondary, amines has been converted to the corresponding tertiary amines, including [N-13C]-labelled drugs, in good to excellent yields at mild conditions (see scheme; dppp=(1,3-bis(diphenylphosphino)propane)).
N-Methylation of amine and nitro compounds with CO2/H2 catalyzed by Pd/CuZrOx under mild reaction conditions
Cui, Xinjiang,Zhang, Yan,Deng, Youquan,Shi, Feng
supporting information, p. 13521 - 13524 (2015/01/09)
An active Pd/ZrCuOx catalyst was prepared for the reductive amination of CO2. The N-methylation of amines and nitro compounds with CO2/H2 can be realized with up to 97% yield under relatively mild reaction condi
Carbon Dioxide Reduction to Methylamines under Metal-Free Conditions
Blondiaux, Enguerrand,Pouessel, Jacky,Cantat, Thibault
, p. 12186 - 12190 (2016/02/23)
The first metal-free catalysts are reported for the methylation of amines with carbon dioxide. Proazaphosphatrane superbases prove to be highly active catalysts in the reductive functionalization of CO2, in the presence of hydroboranes. The new methodology enables the methylation of N-H bonds in a wide variety of amines, including secondary amines, with increased chemoselectivity. Organocatalysis: Proazaphosphatrane superbases prove to be highly active catalysts in the reductive functionalization of CO2, in the presence of hydroboranes. The new method makes possible the methylation of N-H bonds in a wide variety of amines, including secondary amines (see picture), with increased chemoselectivity.
Selective methylation of amines with carbon dioxide and H2
Li, Yuehui,Sorribes, Ivan,Yan, Tao,Junge, Kathrin,Beller, Matthias
supporting information, p. 12156 - 12160 (2013/12/04)
Put a label on it: Carbon dioxide with H2 is shown to be an efficient and selective methylation reagent for aromatic and aliphatic amines (see scheme; acac=acetylacetonate, triphos = 1,1,1- tris(diphenylphosphanylmethyl)ethane). A variety of functionalized amines including 13C-labelled drugs were obtained with good yields and functional-group tolerance. Copyright
