3405-42-3Relevant academic research and scientific papers
Simplified preparation of a graphene-co-shelled Ni/NiO@C nano-catalyst and its application in theN-dimethylation synthesis of amines under mild conditions
Liu, Jianguo,Ma, Longlong,Song, Yanpei,Zhang, Mingyue,Zhuang, Xiuzheng
supporting information, p. 4604 - 4617 (2021/06/30)
The development of Earth-abundant, reusable and non-toxic heterogeneous catalysts to be applied in the pharmaceutical industry for bio-active relevant compound synthesis remains an important goal of general chemical research.N-methylated compounds, as one of the most essential bioactive compounds, have been widely used in the fine and bulk chemical industries for the production of high-value chemicals. Herein, an environmentally friendly and simplified method for the preparation of graphene encapsulated Ni/NiO nanoalloy catalysts (Ni/NiO@C) was developed for the first time, for the highly selective synthesis ofN-methylated compounds using various functional amines and aldehydes under easy to handle, and industrially applicable conditions. A large number of primary and secondary amines (more than 70 examples) could be converted to the correspondingN,N-dimethylamines with the participation of different functional aldehydes, with an average yield of over 95%. A gram-scale synthesis also demonstrated a similar yield when compared with the benchmark test. In addition, it was further proved that the catalyst could easily be recycled because of its intrinsic magnetism and reused up to 10 times without losing its activity and selectivity. Also, for the first time, the tandem synthesis ofN,N-dimethylamine products in a one-pot process, using only a single earth-abundant metal catalyst, whose activity and selectivity were more than 99% and 94%, respectively, for all tested substrates, was developed. Overall, the advantages of this newly developed method include operational simplicity, high stability, easy recyclability, cost-effectiveness of the catalyst, and good functional group compatibility for the synthesis ofN-methylation products as well as the industrially applicable tandem synthesis process.
Ionic liquid/H2O-mediated synthesis of mesoporous organic polymers and their application in methylation of amines
Yu, Xiaoxiao,Yang, Zhenzhen,Zhang, Hongye,Yu, Bo,Zhao, Yanfei,Liiu, Zhenghui,Ji, Guipeng,Liu, Zhimin
supporting information, p. 5962 - 5965 (2017/07/10)
Mesoporous Tr?ger's base-functionalized polymers (Meso-TBPs) were prepared using a sulfonic acid group functionalized ionic liquid/H2O system, with surface areas up to 431 m2 g-1 and pore sizes of 3-15 nm. Ir(ii) coordinated Meso-TBPs exhibited extraordinary catalytic performance in the N-methylation of amines using methanol.
Efficient Cobalt-Catalyzed Methylation of Amines Using Methanol
Liu, Zhenghui,Yang, Zhenzhen,Yu, Xiaoxiao,Zhang, Hongye,Yu, Bo,Zhao, Yanfei,Liu, Zhimin
supporting information, p. 4278 - 4283 (2017/10/23)
The methylation of amines using methanol is a promising route to synthesize N-methylamines, and the development of cheap and efficient catalytic system for this reaction is of great significance. Herein, we reported a cobalt (Co)-based catalytic system, which was in situ formed from commercially available Co precursor and a tetradentate phosphine ligand P(CH2CH2PPh2)3 combined with K3PO4. This catalystic system was very effective for the selective production of dimethylated products from aliphatic amines and monomethylated ones from aromatic amines. The reaction mechanism was further investigated by control and isotope labelling experiments. (Figure presented.).
A practical regioselective synthesis of alkylthio- or arylthioindoles without the use of smelly compounds such as thiols
Hamashima, Toshihiko,Mori, Yoshiaki,Sawada, Kazunori,Kasahara, Yuko,Murayama, Daisuke,Kamei, Yuto,Okuno, Hiroaki,Yokoyama, Yuusaku,Suzuki, Hideharu
, p. 292 - 303 (2013/05/08)
A convenient method for the synthesis of 3-methylthioindoles has been established which does not use smelly compounds such as thiol derivatives. The method, which introduces an alkyl- or arylthio-group into the C3-position of the indole skeleton, was extended to the direct introduction of a methylthio or bromo group at the C2-position using 3-methylthioindoles. No dimerization occurred, and the reaction mechanism was confirmed. The products have the partial structure of potent anti-methicillin-resistant Staphylococcus aureus (anti-MRSA) bromomethylthioindoles (MC 5-8) isolated from marine algae. Furthermore, this reaction could be applied to the synthesis of 3,3-diindolyl thioether which is a core structure of Echinosulfone A.
Catalytic hydrogenation of amides to amines under mild conditions
Stein, Mario,Breit, Bernhard
supporting information, p. 2231 - 2234 (2013/03/28)
Under (not so much) pressure: A general method for the hydrogenation of tertiary and secondary amides to amines with excellent selectivity using a bimetallic Pd-Re catalyst has been developed. The reaction proceeds under low pressure and comparatively low temperature. This method provides organic chemists with a simple and reliable tool for the synthesis of amines. Copyright
SULFIDE SCAVENGERS, METHODS FOR MAKING AND METHODS FOR USING THEM
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Paragraph 0069, (2013/07/19)
Methods for making sulfide scavenging compositions are provided. The method comprises reacting at least one secondary amine with at least one aldehyde and solvent in the presence of a catalyst to form a reaction composition, wherein a reaction temperature is less than or equal to 90 °C. Sulfide scavengers using the above method are also disclosed. Methods for removing sulfides from fluid streams are also provided. The methods include adding the above sulfide scavengers to fluid streams.
Dialkylamino and nitrogen heterocyclic analogues of hexadecylphosphocholine and cetyltrimetylammonium bromide: Effect of phosphate group and environment of the ammonium cation on their biological activity
Lukac, Milos,Mojzis, Jan,Mojzisova, Gabriela,Mrva, Martin,Ondriska, Frantisek,Valentova, Jindra,Lacko, Ivan,Bukovsky, Marian,Devinsky, Ferdinand,Karlovska, Janka
scheme or table, p. 4970 - 4977 (2010/02/27)
A series of dialkylamino and nitrogen heterocyclic analogues of hexadecylphosphocholine and cetyltrimethylammonium bromide have been synthesized. The prepared compounds exhibit significant cytotoxic, antifungal and antiprotozoal activities. Alkylphosphocholines possess higher antifungal activity against Candida albicans in comparison with quaternary ammonium compounds. However, quaternary ammonium compounds exhibit significant higher activity against human tumor cells and Acanthamoeba lugdunensis compared to alkylphosphocholines. In addition, their haemolytic toxicity has been investigated. The relationship between structure and biological activity of the tested compounds is discussed.
Use of Zinc Borohydride in Reductive Amination: An Efficient and Mild Method for N-Methylation of Amines
Bhattacharyya, Sukanta,Chatterjee, Arindam,Duttachowdhury, Shiti, Kantha
, p. 1 - 2 (2007/10/02)
An efficient method for the reductive methylation of amines using paraformaldehyde, zinc chloride and zinc borohydride is described.
Alkylations Using Methyltrialkoxyphosphonium Tetrafluoroborate Salts. Synthetic and Mechanistic Aspects of Methyl, Ethyl, 2-Propyl, and 2-Octyl Group Transfers
Fry, Slaton E.,Pienta, Norbert J.
, p. 4877 - 4880 (2007/10/02)
Trialkyl phosphites, (RO)3P for R = methyl, ethyl, 2-propyl, and 2-octyl, were alkylated with Meerwein's salt (Me3O+BF4-) to yield the corresponding trialkoxymethylphosphonium tetrafluoroborate salts.These salts, which are all molten at room temperature, were reacted neat or in solvents with a series of nucleophiles.Thus, a variety of O, N, S, and halogen nucleophiles reacted by substitution at the R group C-O bond to give high yields after a trivial workup procedure.Rates of reaction were measured for substituted benzoic acids (4-XC6H4CO2H; X= CH3, t-Bu, CH3O, H, CF3, CN, NO2) with the neat salts under pseudo-first-order conditions or with the salt in CH3CN under second order conditions.The resulting Hammett plots indicate very little change in sensivity to the substituents when R = isopropyl compared with R = methyl and when the salt itself instead of CH3CN is solvent.
NOUVELLE METHODE DE PREPARATION D'AMINES TERTIAIRES
Kapnang, H.,Charles, G.
, p. 1597 - 1600 (2007/10/02)
Tertiary amines R-N(CH2R')2 are obtained by reacting 1,5,3-perhydrodioxazepines derivatived from primary amines RNH2, with Grignard reagents R'MgX.
