5369-34-6Relevant academic research and scientific papers
Elucidation of the electrochemical behavior of phenothiazine-based polyaromatic amines
Peterson, Brian M.,Shen, Luxi,Lopez, Gerickson J.,Gannett, Cara N.,Ren, Dong,Abru?a, Héctor D.,Fors, Brett P.
, p. 4244 - 4249 (2019)
Polyarlylamines with discrete redox active groups in the polymer backbone represent a promising class of cathode materials for electrical energy storage applications. In this area, our group recently reported a set of phenothiazine-based polymers that exh
Ru-Catalyzed Selective Catalytic Methylation and Methylenation Reaction Employing Methanol as the C1 Source
Biswas, Nandita,Srimani, Dipankar
, p. 10544 - 10554 (2021/07/31)
Methanol can be employed as a green and sustainable methylating agent to form C-C and C-N bonds via borrowing hydrogen (BH) methodology. Herein we explored the activity of the acridine-derived SNS-Ru pincer for the activation of methanol to apply it as a C1 building block in different reactions. Our catalytic system shows great success toward the β-C(sp3)-methylation reaction of 2-phenylethanols to provide good to excellent yields of the methylated products. We investigated the mechanistic details, kinetic progress, and temperature-dependent product distribution, which revealed the slow and steady generation of in situ formed aldehyde, is the key factor to get the higher yield of the β-methylated product. To establish the environmental benefit of this reaction, green chemistry metrics are calculated. Furthermore, dimerization of 2-naphthol via methylene linkage and formation of N-methylation of amine are also described in this study, which offers a wide range of substrate scope with a good to excellent yield.
Highly selective hydrogenation of amides catalysed by a molybdenum pincer complex: Scope and mechanism
Leischner, Thomas,Artús Suarez, Lluis,Spannenberg, Anke,Junge, Kathrin,Nova, Ainara,Beller, Matthias
, p. 10566 - 10576 (2019/12/02)
A series of molybdenum pincer complexes has been shown for the first time to be active in the catalytic hydrogenation of amides. Among the tested catalysts, Mo-1a proved to be particularly well suited for the selective C-N hydrogenolysis of N-methylated formanilides. Notably, high chemoselectivity was observed in the presence of certain reducible groups including even other amides. The general catalytic performance as well as selectivity issues could be rationalized taking an anionic Mo(0) as the active species. The interplay between the amide CO reduction and the catalyst poisoning by primary amides accounts for the selective hydrogenation of N-methylated formanilides. The catalyst resting state was found to be a Mo-alkoxo complex formed by reaction with the alcohol product. This species plays two opposed roles-it facilitates the protolytic cleavage of the C-N bond but it encumbers the activation of hydrogen.
Method for selectively preparing N-monomethylamine compounds by using nitro compound as raw material
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Paragraph 0035; 0036, (2018/11/03)
The invention discloses a method for selectively preparing N-monomethylamine compounds by using a nitro compound as a raw material. The method uses the nitro compound as the reaction raw material, formaldehyde as a methylating agent and a hydrogen gas as a reducing agent, in the presence of a supported type catalyst, a reaction is performed for 2-48 h at temperature of 10-180 DEG C in a reaction medium, and therefore the N-monomethylamine compounds are obtained, wherein the catalyst is at least one catalyst supported by palladium, platinum, ruthenium or rhodium. The method disclosed by the invention is simple, and can obtain the target product in a low-cost high-yield and high-selectivity manner; the method simplifies reaction steps, improves reaction efficiency, reduces reaction costs, and avoids separation of an intermediate product primary amine with high toxicity, easy deterioration and difficult storage; the method adopts the H2 as the reducing agent, thereby being clean, inexpensive and environmentally friendly; and the reaction conditions of the method are mild, and the catalyst is non-corrosive and easy to separate and reuse.
Structure based drug design and in vitro metabolism study: Discovery of N-(4-methylthiophenyl)-N,2-dimethyl-cyclopenta[d]pyrimidine as a potent microtubule targeting agent
Xiang, Weiguo,Choudhary, Shruti,Hamel, Ernest,Mooberry, Susan L.,Gangjee, Aleem
, p. 2437 - 2451 (2018/04/16)
We report a series of tubulin targeting agents, some of which demonstrate potent antiproliferative activities. These analogs were designed to optimize the antiproliferative activity of 1 by varying the heteroatom substituent at the 4′-position, the basicity of the 4-position amino moiety, and conformational restriction. The potential metabolites of the active compounds were also synthesized. Some compounds demonstrated single digit nanomolar IC50 values for antiproliferative effects in MDA-MB-435 melanoma cells. Particularly, the S-methyl analog 3 was more potent than 1 in MDA-MB-435 cells (IC50 = 4.6 nM). Incubation of 3 with human liver microsomes showed that the primary metabolite of the S-methyl moiety of 3 was the methyl sulfinyl group, as in analog 5. This metabolite was equipotent with the lead compound 1 in MDA-MB-435 cells (IC50 = 7.9 nM). Molecular modeling and electrostatic surface area were determined to explain the activities of the analogs. Most of the potent compounds overcome multiple mechanisms of drug resistance and compound 3 emerged as the lead compound for further SAR and preclinical development.
Highly Selective N-Monomethylanilines Synthesis from Nitroarene and Formaldehyde via Kinetically Excluding of the Thermodynamically Favorable N,N-Dimethylation Reaction
Wang, Hongli,Yuan, Hangkong,Yang, Benqun,Dai, Xingchao,Xu, Shan,Shi, Feng
, p. 3943 - 3949 (2018/05/23)
The synthesis of N-monomethylamine remains a challenging topic because the N,N-dimethylation reaction is thermodynamically favorable. In this work, the kinetically controlled N-monomethylamine synthesis from nitroarene and paraformaldehyde/H2 is reported to have superhigh N-monomethylamine selectivity in the presence of a Pd/TiO2 catalyst. The superior selectivity should be attributed to the preferential adsorption of the primary amine over N-monomethylamine on the Pd/TiO2 surface, as elucidated by NH3/Me2NH-TPD, while the excellent catalytic activity could be associated with the good H2 activation ability and high amine adsorbing capacity of the catalyst, as elucidated by NH3-TPD and H2-TPR tests. Good results were obtained with a variety of nitroarenes containing methyl, methoxyl, hydroxyl, fluoride, trifluoromethyl, ester, and amide substituents as starting materials, and the potential synthetic utility of this protocol in pharmaceutical is illustrated by N-monomethylation of drug molecules, such as clinidipine, nimesulide, procaine, and methyl aminosalicylate.
Direct condensation of functionalized sp3 carbons with formanilides for enamine synthesis using an in situ generated HMDS amide catalyst
Taneda, Hiroshi,Inamoto, Kiyofumi,Kondo, Yoshinori
, p. 6523 - 6525 (2014/06/09)
The efficient synthesis of functionalized enamines including β-enaminoesters was effectively accomplished by the direct condensation of functionalized sp3 carbanions such as acetates with formamides using in situ generated HMDS base from catalytic cesium fluoride and stoichiometric tristrimethylsilylamine. This journal is the Partner Organisations 2014.
Phosphoramidate tantalum complexes for room-temperature C-H functionalization: Hydroaminoalkylation catalysis
Garcia, Pierre,Lau, Ying Yin,Perry, Mitchell R.,Schafer, Laurel L.
, p. 9144 - 9148 (2013/09/12)
A cooled reaction: Phosphoramidate-ClTaMe3 complexes promote the first example of room-temperature hydroaminoalkylation catalysis. This reaction can be realized under solvent-free conditions and with challenging substrates such as styrenes and dialkyl amines. When using a vinylsilane substrate, for the first time the linear regioisomer is obtained preferentially using a Group5 metal. TBS=tert-butyldimethylsilyl, TMS=trimethylsilyl. Copyright
Polycationic states of oligoanilines based on Wurster's blue
Ito, Akihiro,Sakamaki, Daisuke,Ino, Haruhiro,Taniguchi, Aya,Hirao, Yasukazu,Tanaka, Kazuyoshi,Kanemoto, Katsuichi,Kato, Tatsuhisa
experimental part, p. 4441 - 4450 (2010/03/03)
Polycations of two oligoanilines based on Wurster's blue, N,N',N-tris[4-(dimethylamino)phenyl]-N,N',N-trimethyl1,3,5-benzenetriamine (2) and N,N'-bis(3-{N-[4-(dimethylamino)phenyl]-N-methylamino}phenyl)-N,N'-dimethyl- pphenylenediamine (3), have been generated efficiently by a stepwise oxidation procedure, Their redox behavior was characterized in terms of the embedded p-phenylenediamine (PD) units and their intramolecular connectivity, EPR analysis of the oxidized 2 and 3 species revealed the existence of high-spin species in solution. It was found that spin multiplicities of the dominant polycationic species of 2 and 3 formed by 3 equiv, of oxidant can be assigned to quartet: and doublet states, respectively on the basis of pulsed EPR spectroscopy, These results demonstrate that the intramolecular connectivity between the spin-containing units decisively influences the spin preference of the multispin systems based on oligoanilines.
N-phenyl-N-acetamidoglycinamides, their preparation and medicaments containing them
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, (2008/06/13)
Compounds of formula: STR1 in which R1 represents a hydrogen atom or an alkyl, alkoxycarbonyl or an unsubstituted or substituted phenyl radical, R2 represents a hydrogen atom or an unsubstituted or substituted alkyl radical, R3 represents an alkyl, phenylalkyl, indanyl, cycloalkylalkyl or an unsubstituted or substituted phenyl radical, or R2 and R3 form a heterocycle together with the nitrogen atom to which they are attached, and R4 represents an unsubstituted or substituted phenyl radical, a naphthyl, indolyl or quinolyl radical or a phenylamino radical in which the phenyl ring is unsubstituted or substituted, their preparation and medicaments containing them.
