- Reviving electrocatalytic reductive amination: A sustainable route from biogenic levulinic acid to 1,5-dimethyl-2-pyrrolidone
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The electrocatalytic reductive amination offers a green pathway to N-containing platform and fine chemicals by using water as a hydrogen source and benign reaction conditions. However, systematic studies about suitable reaction conditions and application to biogenic substrates are rare. Here, we present the electrochemical transformation of levulinic acid to 1,5-dimethyl-2-pyrrolidone. Data from Smirnov et al. for the amination of conventional ketones were validated and extended by systematically investigating the impact of electrode material, substrate concentration, current density, solvent, electrolyte, and pH value. High substrate concentrations in an aqueous electrolyte with a high pH value enable imine formation and copper is identified as the most selective cathode material at current densities lower than 40 mA cm-2. The application of optimized reaction conditions to levulinic acid, followed by a short heating procedure for dehydrative ring closure, led to 1,5-dimethyl-2-pyrrolidone in 78% yield. The systematic approach of this work presents the first example of an electrochemical levulinic acid amination and provides a methodology for the benign synthesis of other N-containing species. This journal is
- Holzh?user, F. Joschka,Kurig, Nils,Mürtz, Sonja D.,Palkovits, Regina
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supporting information
p. 8428 - 8433
(2021/11/17)
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- Discovery of benzimidazole analogs as a novel interleukin-5 inhibitors
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A series of novel hydroxyethylaminomethylbenzimidazole analogs 5a-y were synthesized and evaluated for their IL-5 inhibitory activity using pro-B Y16 cell line. Among them, 2-(((4-(cyclohexylmethoxy)-1H-benzo[d]imidazol-2-yl)methyl)amino)butan-1-ol (5e, 94.3% inhibition at 30 μM, IC50 = 3.5 μM, cLogP = 4.132) and 3-cyclohexyl-2-(((4-(cyclohexylmethoxy)-1H-benzo[d]imidazol-2-yl)methyl)amino) propan-1-ol (5k, 94.7% inhibition at 30 μM, IC50 = 5.0 μM, cLogP = 6.253) showed the most potent inhibitory activity. The essential feature of SAR (Fig. 5) indicated that the chromenone ring can be replaced by a benzimidazole ring to maintain the inhibitory activity. In addition, the hydroxyethylaminomethyl group was suitable for the IL-5 inhibitory activity. Moreover, the hydrophobic substituents on carbon play an important role in the IL-5 inhibitory activity of these analogs. However, N-substituted analogs did not improve inhibitory activity. In addition, MTT assay of 5e and 5k with normal B lymphoblasts revealed that they had no significant effects on cell viability.
- Boggu, Pulla Reddy,Kim, Youngsoo,Jung, Sang-Hun
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- N-Alkylation of Alkylolamines with Alcohols Over Mesoporous Solid Acid–Base Cs–B–Zr Catalyst
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Abstract: The mesoporous solid acid–base Cs–B–Zr mixed oxides were synthesized using the co-precipitation method followed by a subsequent thermal treatment. The catalytic activity of solid Cs–B–Zr mixed oxide was tested for solvent free acid–base catalysed direct alkylolamines with alcohols as green alkylating agent. The effects of Cs/B/Zr ratio, calcination temperature, reaction conditions, and reaction substrate on the catalytic performance of the catalysts were investigated. The XRD, N2 adsorption–desorption, ICP-OES, FT-IR and NH3/CO2-TPD results showed that the mesoporous structure and acid–base properties of the catalysts play important roles in the reaction. A suitable number of acid and basic sites on the catalyst lead to a high activity for the N-alkylation reaction. Graphical Abstract: A direct N-alkylation of amino alcohol with alcohols has been developed using mixed oxide Cs–B–Zr as an acid–base bifunctionalized catalyst.[Figure not available: see fulltext.]
- Chen, Aimin,Wang, Houyong,Liu, Rui,Bo, Yingying,Hu, Jun
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p. 1182 - 1193
(2016/07/06)
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- METHOD FOR PRODUCING 2-(ISOPROPYLAMINO)ETHANOL
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The present invention relates to a method of producing 2-(isopropylamino)ethanol, including subjecting acetone, 2-aminoethanol, and hydrogen to a vapor-phase catalytic reaction in the presence of a noble metal-containing catalyst. According to the present invention, 2-(isopropylamino)ethanol can be industrially obtained in a large amount and with high efficiency through the vapor-phase catalytic reaction of acetone, 2-aminoethanol, and hydrogen. 2-(Isopropylamino)ethanol is a compound useful as a rawmaterial for a drug, an agricultural chemical, or the like.
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Paragraph 0027
(2015/06/03)
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- Synthesis of pyrrole N-derivatives from oxazolidines
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Transformations of oxazolidine derivatives synthesized from industrially produced amino alcohols, aldehydes, and ketones under basic or acidic catalysis lead to the formation of N-alkyl- and N-(hydroxyalkyl)-substituted pyrroles in 19-81% yields.
- Sadykov, E. Kh.,Stankevich,Lobanova,Klimenko
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p. 219 - 224
(2014/04/17)
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- Process For Preparing Alkylalkanolamines
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The present invention relates to a process for preparing alkylalkanolamines, comprising the reaction of a carbonyl-based compound with a hydroxylalkylamine, in the presence of hydrogen and a catalyst.
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Page/Page column 6-7
(2012/05/20)
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- Pyrithione biocides enhanced by zinc metal ions and organic amines
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The present invention is directed to a stable, soluble, antimicrobial composition concentrate comprising pyrithione or a pyrithione complex in an amount of from about 0.5% to about 30 weight percent, a zinc source in an amount of from about 0.1% to about 10%, and an organic amine component in an amount of from about 30% to about 80%, said percents being based upon the total weight of the composition concentrate. The invention is also directed to methods of controlling the growth of free-living microorganisms or biofilms using the antimicrobial composition of the invention, and products made using the antimicrobial composition of the invention.
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- Process for the continuous preparation of hydroxyalkylamides
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Process for the continuous preparation of hydroxyalkylamides Process for the continuous preparation of hydroxyalkylamides from carboxylic esters and alkanolamines, wherein the reaction of the starting materials is carried out in an extruder or intensive mixer by intensive mixing and brief reaction with supply of heat and simultaneous removal of the alcohol formed and the final product is then isolated.
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- Acid-Catalyzed Decomposition of 1-Alkyltriazolines: A Mechanistic Study
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1-Alkyltriazolines are five-membered cyclic triazenes containing the unusual Z-configuration for the triazene moiety.The hydrolytic decomposition of these compounds in aqueous or mixed acetonitrile-aqueous buffers leads predominantly to the formation of the corresponding 1-alkylaziridines and lesser amounts of 2-(alkylamino)ethanols, alkylamines, and acetaldehyde.The latter two products presumably result from hydrolysis of a rearrangement produkt, N-ethylidenealkylamine.Neither the nature of the 1-alkyl group nor the pH of the medium greatly influences the product distribution, although decomposition in purely aqueous buffers slightly reduces the aziridine yields.The rate of hydrolysis of 1-alkyltriazolines is about twice as fast as that of the analogous acyclic 1,3,3-trialkyltriazenes and varies in the order tert-butyl > isopropyl > ethyl > butyl > methyl > propyl > benzyl.The mechanism of the decomposition is specific acid-catalyzed (A1) involving rapid reversible protonation followed by rate-limiting formation of a 2-(alkylamino)ethyldiazonium ion.The slopes of the log kobs versus pH plots are near -1.0.The solvent deuterium isotope effect, kH2O/kD2O, is in all cases methyl > ethyl.
- Smith, Richard H.,Wladkowski, Brian D.,Taylor, Jesse E.,Thompson, Erin J.,Pruski, Brunon,et al.
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p. 2097 - 2103
(2007/10/02)
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- ELECTROCHEMICAL REDUCTIVE AMINATION. I. AMINATION OF ALIPHATIC KETONES BY PRIMARY AMINES
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The reductive amination of aliphatic ketones in aqueous solutions of primary amines was realized by an electrochemical method.The best yields of the secondary amines were obtained at lead and cadmium cathodes in an aqueous electrolytic solution at pH 11-12.Elongation and branching in the carbon chain of the radicals both of the ketone and of the primary amine lead to a reduction in the yield of the secondary amine.The yield of the secondary amine is mainly determined by the rate of the chemical reaction leading to the formation of the azomethine compound, preceding the electrochemical reduction stage.
- Smirnov, Yu. D.,Tomilov, A. P.
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- OXAZOLIDINES. 1. BASIC CATALYTIC DISPROPORTIONATION OF CYCLOHEXANOSPIRO-2-OXAZOLIDINES: SYNTHESIS OF N-SUBSTITUTED 4,5,6,7-TETRAHYDROINDOLES
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It has been shown that the basic catalytic disproportionation of cyclohexanospiro-2-oxazolidines in the presence of potasium hydroxide or sodium methylate leads to N-substituted 4,5,6,7-tetrahydroindoles with a yield of up to 73percent.The influence of the character of substituents at the nitrogen atom of oxazolidine on the course of the reaction has been established.
- Kukharev, B.F.,Stankevich, V.K.,Kukhareva, V.A.
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p. 437 - 439
(2007/10/02)
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- Reductive Alkylation of β-Alkanolamines with Carbonyl Compounds and Sodium Borohydride
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A synthesis of secondary alkylalkanolamines from primary alkanolamines in a rapid process in which overalkylation is virtually suppressed is described.The procedure combines the ease of formation of oxazolidines from alkanolamines with aldehydes or ketones in absolute ethanol and the lability of the newly formed C-O bond toward sodium borohydrode.The entire process is carried out in 15-35 min depending on the carbonyl substrate.
- Saavedra, Joseph E.
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p. 2271 - 2273
(2007/10/02)
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- BORANE-TETRAHYDROFURAN AS A USEFUL REAGENT IN THE N-MONOALKYLATION OF AMINES AND AMINOALCOHOLS BY CARBONYL COMPOUNDS.
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A new procedure for the high-yield N-monoalkylation of primary aromatic and aliphatic amines is described.
- Morales, Hilda R.,Perez-Juarez, Martin,Cuellar, Laura,Mendoza, Lourdes,Fernandez, Hector,Contreras, Rosalinda
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p. 1213 - 1220
(2007/10/02)
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- Syntheses of α-C-Functionalized N-Nitrodialkylamines: Esters of methanol and 1-ethanol
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The α-acetoxynitramines 5 and 6 - important derivatives for studying the biological properties of N-nitrodialkylamines 4 - have been synthesized, and the stability of the ester bond has been investigated.The reaction of N-nitroalkylamines 7 with 1-halogenoethyl acetates 9, thought to afford 6, yielded the diazene N-oxides 10 as the main products.
- Plesch, Winfried,Wiessler, Manfred
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p. 1494 - 1503
(2007/10/02)
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