15184-99-3Relevant academic research and scientific papers
Electrochemical Dehydrogenative Imidation of N-Methyl-Substituted Benzylamines with Phthalimides for the Direct Synthesis of Phthalimide-Protected gem-Diamines
Lian, Fei,Sun, Caocao,Xu, Kun,Zeng, Chengchu
supporting information, p. 156 - 159 (2019/01/11)
A general and green electrochemical dehydrogenative method for the imidation of N-methyl benzylamines with phthalimides with excellent regioselectivities is reported for the first time. This operationally simple method offers a valuable tool to obtain str
Direct Synthesis of N,N-Dimethylated and β-Methyl N,N-Dimethylated amines from nitriles using methanol: Experimental and computational studies
Paul, Bhaskar,Shee, Sujan,Panja, Dibyajyoti,Chakrabarti, Kaushik,Kundu, Sabuj
, p. 2890 - 2896 (2018/04/14)
Direct and selective synthesis of N,N-dimethylated amines from nitriles using methanol as C1 building blocks is reported using an air- and moisture-stable ruthenium complex. Following this process, various aromatic as well as aliphatic nitriles were converted to the corresponding N-methylated amines. Interestingly, tandem C-methylation as well as N-methylation was achieved by introducing multiple methyl groups. The practical aspect of this process was revealed by preparative-scale reactions with different nitriles and the synthesis of anti-allergic drug "avil". Several kinetic experiments and detailed DFT calculations were carried out to understand the mechanism of this process.
Lewis Acid-Catalyzed Reductive Amination of Aldehydes and Ketones with N,N-Dimethylformamide as Dimethylamino Source, Reductant and Solvent
Yang, Luo,Lin, Jie,Kang, Lei,Zhou, Wang,Ma, Da-You
supporting information, p. 485 - 490 (2018/01/15)
A practical zinc acetate dihydrate-catalyzed reductive amination of various carbonyl compounds with N,N-dimethylformamide (DMF) as dimethylamino (Me2N) source, reductant and solvent has been developed. This reaction shows broad substrate scope,
Catalytic reduction of amides to amines by electrophilic phosphonium cations via FLP hydrosilylation
Augurusa, Alessandra,Mehta, Meera,Perez, Manuel,Zhu, Jiangtao,Stephan, Douglas W.
supporting information, p. 12195 - 12198 (2016/10/21)
A catalytic methodology for the conversion of amides to amines is reported. Of the 25 examples described, 14 examples involve the reduction of N-trifluoroacetamides to the corresponding trifluoroethylamines. These reductions are achieved by catalytic hydrosilylation of the amide mediated by an electrophilic phosphonium cation (EPC) catalyst.
Dual antitumor and antiangiogenic activity of organoplatinum(II) complexes
Zamora, Ana,Pérez, Sergio A.,Rodríguez, Venancio,Janiak, Christoph,Yellol, Gorakh S.,Ruiz, José
, p. 1320 - 1336 (2015/03/04)
A library of over 20 cycloplatinated compounds of the type [Pt(dmba-R)LCl] (dmba-R = C,N-dimethylbenzylamine-like ligand; R being MeO, Me, H, Br, F, CF3, and NO2 substituents in the R5 or R4 position of the phenyl ring; L = DMSO and P(C6H4CF3-p)3) has been prepared. All compounds are active in both human ovarian carcinoma A2780 cells and cisplatin-resistant A2780cisR cells, with most of the DMSO platinum complexes exhibiting IC50 values in the submicromolar range in the A2780 cell line. Interestingly, DMSO platinum complexes show low cytotoxicity in the nontumorigenic kidney cell line BGM and therefore high selectivity factors SF. In addition, some of the DMSO platinum complexes effectively inhibit angiogenesis in the human umbilical vein endothelial cell line EA.hy926. These are the first platinum(II) complexes reported to inhibit angiogenesis at a close concentration to their IC50 in A2780 cells, turning them into dual cytotoxic and antiangiogenic compounds.
Simple Amine-Directed Meta-Selective C-H Arylation via Pd/Norbornene Catalysis
Dong, Zhe,Wang, Jianchun,Dong, Guangbin
supporting information, p. 5887 - 5890 (2015/05/27)
Herein we report a highly meta-selective C-H arylation using simple tertiary amines as the directing group. This method takes advantage of Pd/norbornene catalysis, offering a distinct strategy to control the site selectivity. The reaction was promoted by commercially available AsPh3 as the ligand and a unique "acetate cocktail". Aryl iodides with an ortho electron-withdrawing group were employed as the coupling partner. A wide range of functional groups, including some heteroarenes, are tolerated under the reaction conditions. In addition, the amine directing group can be easily installed and transformed to other common versatile functional groups. We expect this C-H functionalization mode to have broad implications for developing other meta-selective transformations beyond this work.
Base-promoted N-alkylation using formamides as the N-sources in neat water
Chen, Wen-Xin,Zhang, Cai-Yun,Shao, Li-Xiong
, p. 880 - 885 (2014/01/23)
An efficient catalyst-free, alternative method for the C-N bond formation reaction of alkyl electrophiles using formamides as the N-sources was achieved under mild conditions. The reaction possesses the advantages of a broad range of substrates scope and wide functional group tolerance. It should also be noted that this process was performed using the environmentally benign water as the sole solvent, and high yield can also be achieved in ten-gram scale.
Highly efficient amination in neat water of benzyl chlorides with dialkylformamides catalysed by N-heterocyclic carbene-palladium(II)-1- methylimidazole complex
Chen, Wen-Xin,Zhang, Cai-Yun,Lu, Jian-Mei
, p. 611 - 614 (2013/11/06)
Dialkylformamides are excellent N-sources in the amination of benzyl chlorides when catalysed by a NHC-Pd(II)-Im complex. In the presence of NaOH and the catalyst, variously substituted benzyl chlorides and five different dialkylformamides reacted smoothly to afford the corresponding N,N-dialkyl-benzylamines in good to almost quantitative yields in eco-friendly solvent water at 50 °C within 3 h.
LiCl-Promoted Pd(ii)-catalyzed ortho carbonylation of N,N- dimethylbenzylamines
Li, Hu,Cai, Gui-Xin,Shi, Zhang-Jie
supporting information; experimental part, p. 10442 - 10446 (2011/01/08)
Palladium-catalyzed highly regioselective carbonylation of substituted N,N-dimethylbenzylamines with the assistance of LiCl was developed. The ortho-functionalized N,N-dimethylbenzylamine was further transformed into ortho-methyl benzoate under mild conditions. These two transformations could be combined into one pot to produce the desired product in moderate yield. Applications of this methodology to synthesize the fragments of variolaric acid were also studied.
Anacardic acid derivatives as inhibitors of glyceraldehyde-3-phosphate dehydrogenase from Trypanosoma cruzi
Pereira, Junia M.,Severino, Richele P.,Vieira, Paulo C.,Fernandes, Joao B.,da Silva, M. Fatima G.F.,Zottis, Aderson,Andricopulo, Adriano D.,Oliva, Glaucius,Correa, Arlene G.
, p. 8889 - 8895 (2008/12/23)
Chagas' disease, a parasitic infection caused by the flagellate protozoan Trypanosoma cruzi, is a major public health problem affecting millions of individuals in Latin America. On the basis of the essential role in the life cycle of T. cruzi, the glycolytic enzyme glyceraldehyde-3-phosphate dehydrogenase (GAPDH) has been considered an attractive target for the development of novel antitrypanosomatid agents. In the present work, we describe the inhibitory effects of a small library of natural and synthetic anacardic acid derivatives against the target enzyme. The most potent inhibitors, 6-n-pentadecyl- (1) and 6-n-dodecylsalicilic acids (10e), have IC50 values of 28 and 55 μM, respectively. The inhibition was not reversed or prevented by the addition of Triton X-100, indicating that aggregate-based inhibition did not occur. In addition, detailed mechanistic characterization of the effects of these compounds on the T. cruzi GAPDH-catalyzed reaction showed clear noncompetitive inhibition with respect to both substrate and cofactor.
