622-93-5Relevant academic research and scientific papers
Iron-Catalyzed Anti-Markovnikov Hydroamination and Hydroamidation of Allylic Alcohols
Ma, Wei,Zhang, Xiaohui,Fan, Juan,Liu, Yuxuan,Tang, Weijun,Xue, Dong,Li, Chaoqun,Xiao, Jianliang,Wang, Chao
supporting information, p. 13506 - 13515 (2019/09/09)
Hydroamination allows for the direct access to synthetically important amines. Controlling the selectivity of the reaction with efficient, widely applicable, and economic catalysts remains challenging, however. This paper reports an iron-catalyzed formal anti-Markovnikov hydroamination and hydroamidation of allylic alcohols, which yields γ-amino and γ-amido alcohols, respectively. Homoallylic alcohol is also feasible. The catalytic system, consisting of a pincer Fe-PNP complex (1-4 mol %), a weak base, and a nonpolar solvent, features exclusive anti-Markovnikov selectivity, broad substrate scope (>70 examples), and good functional group tolerance. The reaction could be performed at gram scale and applied to the synthesis of drug molecules and heterocyclic compounds. When chiral substrates are used, the stereochemistry and enantiomeric excess are retained. Further application of the chemistry is seen in the functionalization of amino acids, natural products, and existing drugs. Mechanistic studies suggest that the reaction proceeds via two cooperating catalytic cycles, with the iron complex catalyzing a dehydrogenation/hydrogenation process while the amine substrate acts as an organocatalyst for the Michael addition step.
Synthesis and Antibacterial Activity of Polymerizable Acryloyloxyalkyltriethyl Ammonium Salts
Mancuso, Raffaella,Amuso, Roberta,Armentano, Biagio,Grasso, Giuseppe,Rago, Vittoria,Cappello, Anna Rita,Galiano, Francesco,Figoli, Alberto,De Luca, Giorgio,Hoinkis, Jan,Gabriele, Bartolo
, p. 1235 - 1244 (2017/10/06)
This study reports an efficient and practical synthetic approach for the synthesis of a particularly important class of polymerizable quaternary ammonium salts (PQASs), that is, acryloxyalkyltriethylammonium bromides (AATEABs), which may find application as antimicrobial coatings for commercial membranes with antifouling and anti-biofouling properties, to be used for wastewater treatment. The synthetic method is based on a simple two-step procedure from commercially available substrates, entirely carried out under air and without any need for chromatographic purification. All the newly synthesized AATEABs were tested for their antimicrobial activity, and the results showed that AATEABs bearing an alkyl chain of 11 and particularly 12 carbon atoms possessed significant activity against Gram positive bacteria and yeast strains.
REDUCTIVE PREPARATION OF TERTIARY DIMETHYLAMINES FROM NITRILES
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Paragraph 0052; 0053, (2017/04/04)
This disclosure describes a low temperature process for the preparation of dimethyl amines from nitriles via reductive amination. In some embodiments, the process proceeds under mild conditions with aqeuous dimethylamine and show an unexpected rate acceleration by the inclusion of an acid addition salt of the dimethylamine.
Reductive amination of nitriles using transfer hydrogenation
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Page/Page column 7; 8, (2016/11/09)
This disclosure describes a low temperature process for the preparation of tertiary amines from nitriles and secondary amines via reductive amination using transfer hydrogenation. The process can use a nitrile and a dialkylamine and proceeds under surprisingly mild conditions using a palladium catalyst and the corresponding dialkylammonium formate as the hydrogen donor, and show a pronounced acceleration in the presence of water.
Formation of 3-hydroxyalkyl carbamates from carbon dioxide, amines and oxetanes
Ishii, Shigeru,Zhou, Ming,Yoshida, Yasuhiko,Noguchi, Hiromichi
, p. 3207 - 3214 (2007/10/03)
The reactions of carbon dioxide, primary or secondary aliphatic amines and oxetanes at a CO2 pressure of 40 atm at 100-120°C without any catalysts afforded new monocarbamates of 1,3-propanediols, with concomitant formation of amino alcohols from oxetanes and amines.
Aminolysis of Oxetanes: Quite Efficient Catalysis by Lanthanide(III) Trifluoromethansulfonates
Crotti, Paolo,Favero, Lucilla,Macchia, Franco,Pineschi, Mauro
, p. 7089 - 7092 (2007/10/02)
Ln(III)trifluoromethansulfonates in CH2Cl2 efficiently catalyze the aminolysis of trimethylene oxide, 2-octyl-, and 2-phenyloxetane, at r.t., to give the corresponding γ-amino alcohols in very good yields.
Mild LIBF4-Promoted Aminolysis of Oxetanes
Chini, Marco,Crotti, Paolo,Favero, Lucilla,Macchia, Franco
, p. 761 - 764 (2007/10/02)
LiBF4 in acetonitrile efficiently catalyzes the aminolysis of trimethylene oxide and 2-octyl oxetane under mild conditions (r.t. or 80 deg C) to give the corresponding γ-amino alcohols in very good yields.
Intramolecular Quenching of Iminium Ions Generated by Photooxidation of Aminoalcohols with Ketones. A New Synthesis of Oxazines and Oxazoles
Cossy, Janine,Guha, Madhumita
, p. 1715 - 1718 (2007/10/02)
The irradiation of tertiary amines in the presence of ketones leads to a regioselective and stereoselective formation of iminium salts which then react to afford the corresponding oxazines or oxazoles. - Key words : Ammoniumyl ions, iminium ions, electron transfer, amines, ketones, tetrahydrooxazine tetrahydrooxazoles.
Omega-quaternary ammonium alkyl esters and thioesters of acidic nonsteroidal antiinflammatory drugs
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, (2008/06/13)
Quaternary ammonium alkyl esters and thioesters of acidic nonsteroidal anti-inflammatory drugs (NSAIDs) are disclosed. These esters and thioesters display the anti--inflammatory profile of the parent NSAIDs with greatly reduced gastrointestinal irritancy, providing a more favorable separation of therapeutic activity and toxicological side effects than the parent NSAIDs.
