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Journal articles on the topic 'Amination reaction'

Author: Grafiati

Published: 4 June 2021

Last updated: 4 March 2023

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1

Tang, Jo Sing Julia, Kristin Schade, Lucas Tepper, Sany Chea, Gregor Ziegler, and Ruben R. Rosencrantz. "Optimization of the Microwave Assisted Glycosylamines Synthesis Based on a Statistical Design of Experiments Approach." Molecules 25, no. 21 (November 4, 2020): 5121. http://dx.doi.org/10.3390/molecules25215121.

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Glycans carry a vast range of functions in nature. Utilizing their properties and functions in form of polymers, coatings or glycan derivatives for various applications makes the synthesis of modified glycans crucial. Since amines are easy to modify for subsequent reactions, we investigated regioselective amination conditions of different saccharides. Amination reactions were performed according to Kochetkov and Likhoshertov and accelerated by microwave irradiation. We optimized the synthesis of glycosylamines for N-acetyl-d-galactosamine, d-lactose, d-glucuronic acid and l-(−)-fucose using the design of experiments (DoE) approach. DoE enables efficient optimization with limited number of experimental data. A DoE software generated a set of experiments where reaction temperature, concentration of carbohydrate, nature of aminating agent and solvent were investigated. We found that the synthesis of glycosylamines significantly depends on the nature of the carbohydrate and on the reaction temperature. There is strong indication that high temperatures are favored for the amination reaction.

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2

Suginome, Michinori. "Aminoboranes as new iminium ion generators in amination reactions." Pure and Applied Chemistry 78, no. 7 (January 1, 2006): 1377–87. http://dx.doi.org/10.1351/pac200678071377.

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The utilization of aminoborane derivatives in amination reactions such as Strecker-type aminative cyanation, Mannich-type reaction, and reductive amination is described. Bis(dialkylamino)cyanoboranes and bis(dialkylamino)boron enolates underwent the concurrent transfer of the amino group and either the cyano or the enoxy group from the boron to carbonyl carbon atom in their reaction with aldehydes, leading to the formation of α-amino nitriles and β-amino ketones, respectively. Bis(dialkylamino)borane derivatives that lack the additional nucleophilic groups on the boron atoms were found to serve as effective generators of iminium ions from aldehydes. In the presence of these aminoboranes, reactions of aldehydes with ketene silyl acetals or silyl enol ethers take place, giving Mannich-type products, i.e., β-amino esters and ketones, selectively. Using diisopropylamino-substituted boron compounds, which are designed as "universal" iminium ion generators, reactions of free sec-amines, aldehydes, and ketene silyl acetals proceed efficiently, giving β-amino esters in which the amino groups are derived exclusively from the free amines. The use of the universal iminium ion generator is also effective for reductive amination of aldehydes, in which NaBH4 is used as a hydride donor.

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3

Beverina, Luca, Luca Vaghi, Alessandro Sanzone, Mauro Sassi, Simone Pagani, and Antonio Papagni. "Synthesis of Fluorinated Acridines via Sequential Micellar Buchwald–Hartwig Amination/Cyclization of Aryl Bromides." Synthesis 50, no. 08 (February 26, 2018): 1621–28. http://dx.doi.org/10.1055/s-0036-1591937.

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Fluorinated unsymmetrical acridines are efficiently prepared by means of a tandem micellar Buchwald–Hartwig amination followed by an acid-promoted cyclization. The overall process is advantageous with respect to previously described protocols both in terms of efficiency and sustainability. The role of the cosolvent in the amination step is highlighted, demonstrating that rather than resorting to highly expensive catalysts, Buchwald–Hartwig aminations can be straightforwardly carried out by tuning the reaction site polarity.

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4

Radhika, Sankaran, Mohan Neetha, Thaipparambil Aneeja, and Gopinathan Anilkumar. "Microwave-assisted Amination Reactions: An Overview." Current Organic Chemistry 24, no. 19 (December 1, 2020): 2235–55. http://dx.doi.org/10.2174/1385272824999200914111246.

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C-N coupling reactions were found to be attractive among researchers owing to the importance of C-N bond formation in heterocyclic synthesis. Hence C-N bond formation via amination reaction with the assistance of microwave radiations gained significant attraction recently. Microwave-assisted reactions are greener, faster and generally efficient compared to the conventional thermal reactions offering better purity of the product with enhancement in the yield. It was surprisingly revealed that several new advancements in amination reactions were highly influenced by this greener technology. This first review on microwave-assisted amination reaction focuses on the novel amination strategies that emerged with the help of microwave methodology, and covers literature up to 2019.

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5

Wang, Zhipeng A., Yan-Yu Liang, and Ji-Shen Zheng. "Reductive Amination/Alkylation Reactions: The Recent Developments, Progresses, and Applications in Protein Chemical Biology Studies." Current Organic Synthesis 15, no. 6 (August 29, 2018): 755–61. http://dx.doi.org/10.2174/1570179415666180522093905.

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The chemical modifications of proteins or protein complexes have been a challenging but fruitful task in the post-genomic era. Bioorthogonal reactions play an important role for the purpose of selective functionalization, localization, and labeling of proteins with natural or non-natural structures. Among these reactions, reductive amination stands out as one of the typical bioorthogonal reactions with high efficiency, good biocompatibility, and versatile applications. However, not many specific reviews exist to discuss the mechanism, kinetics, and their applications in a detailed manner. In this manuscript, we aim to summarize some current developments and mechanistic studies of reductive amination reaction and its applications. We hope reductive amination reaction can contribute to a wider scope of protein chemistry research en route in the chemical biology frontier as one of the well-known bioorthogonal reactions.

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6

Li, Zhen, Yan Ding, and Jin Liu. "Study on Primary Reaction Kinetics of Melamine Aminated Monomethoxylpoly (ethylene Glycol)." Advanced Materials Research 450-451 (January 2012): 374–78. http://dx.doi.org/10.4028/www.scientific.net/amr.450-451.374.

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The reaction kinetics of amination of monomethoxylpoly (ethylene glycol) (mPEG) with melamine (MA) at the molar ratio of 1:1 was studied by FTIR. This amination reaction was carried out with potassium hydroxide as reaction catalyst under high-pressure conditions at different temperature (160 °C, 170 °C, 180 °C, and 190°C) for different time (2 h, 3 h, 4 h, 5 h and 6 h). A series of melamine aminated monomethoxylpoly (ethylene glycol) (MA-mPEG) were synthesized, and the long chain of polyethylene glycol ether was grafted on the amino groups of melamine by amination. The amination kinetics parameter of reaction order and the activation energy are about 1.5 and 45 KJ/mol, respectively. In addition, the grafting amination yield increased with the number average molecular weight of mPEG at the same reaction condition.

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7

Maklad, Noha S. "ChemInform Abstract: Chichibabin Amination Reaction." ChemInform 43, no. 19 (April 12, 2012): no. http://dx.doi.org/10.1002/chin.201219257.

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8

Ojo, Olatunji S., Octavio Miranda, Kyle C. Baumgardner, and Alejandro Bugarin. "Practical regio- and stereoselective azidation and amination of terminal alkenes." Organic & Biomolecular Chemistry 16, no. 48 (2018): 9354–58. http://dx.doi.org/10.1039/c8ob02734j.

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9

Averin, Alexei D., Alexei N. Uglov, Georgii A. Zubrienko, Elena A. Tarasenko, Alexei K. Buryak, and Irina P. Beletskaya. "Synthesis of N- and O-Containing Macrobicycles with Central Biphenyl Moiety via Pd(0)-Catalyzed Amination Reactions." Current Organic Synthesis 14, no. 6 (September 28, 2017): 918–26. http://dx.doi.org/10.2174/1570179414666161230122852.

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Background: Simple, efficient and enough versatile approaches to macrobicycles and macrotricycles, which are of great interest for the coordination of metal cations, were proposed in early 1990s using nucleophilic substitution reactions. Our research group was the first to begin a wide-range synthesis of N- and Ocontaining macrocycles using Pd-catalyzed amination reactions. Objective: The goal of the present research is to develop the catalytic synthesis of nitrogen- and oxygen containing macrobicycles organized around the central biphenyl moiety. Method: The method employed is the Pd(0)-catalyzed amination reactions which led to the formation of the first macrocycle comprising 3,3'-disubstituted biphenyl followed by the modification with two bromobenzyl moieties and the second Pd(0)-catalyzed macrocyclization which afforded target macrobicycles. Results: Macrocycles with the endocyclic 3,3'-disubstituted biphenyl moiety and diazadioxa, diazatrioxa, and tetraamine linkers were synthesized in 26-44% yields using Pd(0)-catalyzed amination reactions. They were modified with two 3-bromobenzyl substituents and introduced in the second Pd(0)-catalyzed macrocyclization to give macrobicycles in 8-27% yields. The result was shown to be dependent on the structure of the reacting compounds. The reaction with diazacrown ether provided a macrotricyclic derivative. Conclusion: An approach to a variety of N- and O-containing macrobicyclic compounds comprising a central biphenyl moiety and two oxadiamine (polyamine) chains via two consecutive Pd(0)-catalyzed amination reactions was elaborated.

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10

Kolmakov, Kirill A. "Reactions of aniline in acetic acid solutions containing cyanuric chloride and hydrogen chloride acceptors." Canadian Journal of Chemistry 85, no. 12 (December 1, 2007): 1070–74. http://dx.doi.org/10.1139/v07-129.

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Two reaction pathways in acetic acid solution containing cyanuric chloride, aniline, and some hydrogen chloride acceptors (triethylamine, sodium acetate, pyridine) were studied. Both aryl amination and acylation can be performed with high yields under proper reaction conditions. Contrary to the only known literature report on the reactions between carbonic acids and cyanuric chloride in the presence of a hydrogen chloride acceptor (triethylamine), it was established that acid chlorides are not formed. A scheme involving the replacement of chlorine atoms by acetate ion in the initial stage was proposed for the acylation of aniline promoted by cyanuric chloride.Key words: acetic acid, acylation, aniline, cyanuric chloride, aryl amination.

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11

Dallagnol, Juliana C. Cunico, Alexandre Orsato, Diogo R. B. Ducatti, Miguel D. Noseda, Maria Eugênia R. Duarte, and Alan G. Gonçalves. "Aqueous semisynthesis of C-glycoside glycamines from agarose." Beilstein Journal of Organic Chemistry 13 (June 23, 2017): 1222–29. http://dx.doi.org/10.3762/bjoc.13.121.

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Agarose was herein employed as starting material to produce primary, secondary and tertiary C-glycoside glycamines, including mono- and disaccharide structures. The semisynthetic approach utilized was generally based on polysaccharide-controlled hydrolysis followed by reductive amination. All reactions were conducted in aqueous media and without the need of hydroxyl group protection. We were able to identify optimal conditions for the reductive amination of agar hydrolysis products and to overcome the major difficulties related to this kind of reaction, also extending it to reducing anhydrosugars. The excess of ammonium acetate, methyl- or dimethylamine, and the use of a diluted basic (pH 11) reaction media were identified as important aspects to achieve improved yields, as well as to decrease the amount of byproducts commonly related to reductive amination of carbohydrates. This strategy allowed the transposition of the 3,6-anhydro-α-L-galactopyranose unit (naturally present in the agarose structure) to all glycamines synthesized, constituting an amino-substituted C-threofuranoside moiety, which is closely related to (+)-muscarine.

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12

Guk, Dmitry A., Olga O. Krasnovskaya, Nikolai V. Zyk, and Elena K. Beloglazkina. "Convenient Synthesis of 2-Thioimidazolone/Menadione Conjugates via a Two-Step Sequence Starting with Direct Amination of Menadione." SynOpen 04, no. 02 (April 2020): 38–43. http://dx.doi.org/10.1055/s-0040-1707519.

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A convenient route to conjugates of 2-thiohydantoins and menadione with linkers of various chemical nature through a two-stage reaction sequence (direct amination of the menadione with a functional amine followed by modification of a functional group) is presented. Optimal conditions for the direct amination of menadione using alkyl amines with substituents such as azide, alkyne, hydroxyl, amine, halogen, and carboxyl have been developed. Further modification of selected functionalities using CuAAC or esterification reactions with 2-thiohydantoines has been performed.

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13

Zhang, Bo-Sheng, Yuke Li, Xue-Ya Gou, Zhe Zhang, Yang An, Xin-Gang Wang, and Yong-Min Liang. "DMAP and PivOH-promoted amination/allenization reaction." Chemical Communications 56, no. 64 (2020): 9202–5. http://dx.doi.org/10.1039/d0cc03749d.

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14

Gou, Xue-Ya, Yuke Li, Xin-Gang Wang, Hong-Chao Liu, Bo-Sheng Zhang, Jia-Hui Zhao, Zhao-Zhao Zhou, and Yong-Min Liang. "Ruthenium-catalyzed ortho-selective CAr–H amination of heteroaryl arenes with di-tert-butyldiaziridinone." Chemical Communications 55, no. 38 (2019): 5487–90. http://dx.doi.org/10.1039/c9cc02499a.

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15

Magdesieva, Tatiana V., and Oleg A. Levitskiy. "Reductive Amination of Aryl Boronic Acids: Parallelism of the Catalytic Reactivity of Transition Metals and Main Group Elements in the C(sp2)–N Bond-Forming Reactions." Synthesis 52, no. 13 (April 20, 2020): 1897–902. http://dx.doi.org/10.1055/s-0039-1690893.

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The results of the DFT studies on the mechanism of the PIII/PV=O catalyzed reductive amination of nitrosoarenes using ArB(OH)2 yielding diaryl amines are reported. This allowed a comparison of the reaction paths and key intermediates of the Cu(I)- and P(III)-mediated reductive aminations of aryl boronic acids using alkylnitrites, nitroso- or nitroarenes, and revealed important similarities in the catalytic reactivity of transition-metal and main-group elements in C(sp2)–N bond-forming reactions. It is shown that both transformations occur via ambiphilic nitrenoid-type key intermediates, the reactivity of which towards the aryl boronic acid is attributed to the presence of both a Lewis acid center (Cu or P) and a Lewis base center (the N or O atoms of the ‘N=O’ component).

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16

Thomas, Annu Anna, Someshwar Nagamalla, and Shyam Sathyamoorthi. "Salient features of the aza-Wacker cyclization reaction." Chemical Science 11, no. 31 (2020): 8073–88. http://dx.doi.org/10.1039/d0sc02554b.

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17

Wang, Juping, Kangcheng Zheng, Ting Li, and Xiaojing Zhan. "Mechanism and Chemoselectivity of Mn-Catalyzed Intramolecular Nitrene Transfer Reaction: C–H Amination vs. C=C Aziridination." Catalysts 10, no. 3 (March 4, 2020): 292. http://dx.doi.org/10.3390/catal10030292.

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The reactivity, mechanism and chemoselectivity of the Mn-catalyzed intramolecular C–H amination versus C=C aziridination of allylic substrate cis-4-hexenylsulfamate are investigated by BP86 density functional theory computations. Emphasis is placed on the origins of high reactivity and high chemoselectivity of Mn catalysis. The N p orbital character of frontier orbitals, a strong electron-withdrawing porphyrazine ligand and a poor π backbonding of high-valent MnIII metal to N atom lead to high electrophilic reactivity of Mn-nitrene. The calculated energy barrier of C–H amination is 9.9 kcal/mol lower than that of C=C aziridination, which indicates that Mn-based catalysis has an excellent level of chemoselectivity towards C–H amination, well consistent with the experimental the product ratio of amintion-to-aziridination I:A (i.e., (Insertion):(Aziridination)) >20:1. This extraordinary chemoselectivity towards C–H amination originates from the structural features of porphyrazine: a rigid ligand with the big π-conjugated bond. Electron-donating substituents can further increase Mn-catalyzed C–H amination reactivity. The controlling factors found in this work may be considered as design elements for an economical and environmentally friendly C–H amination system with high reactivity and high chemoselectivity.

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18

Okano, Kentaro, Hidetoshi Tokuyama, and Tohru Fukuyama. "Copper-mediated aromatic amination reaction and its application to the total synthesis of natural products." Chem. Commun. 50, no. 89 (2014): 13650–63. http://dx.doi.org/10.1039/c4cc03895a.

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The historical background and recent update on copper-mediated aryl amination reactions including the recent C–H aryl amination and its application to the total syntheses of natural products are described.

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19

Zhang, Jun-Ting, Hao-Yang Wang, Xiang Zhang, Fang Zhang, and Yin-Long Guo. "Study of short-lived and early reaction intermediates in organocatalytic asymmetric amination reactions by ion-mobility mass spectrometry." Catalysis Science & Technology 6, no. 17 (2016): 6637–43. http://dx.doi.org/10.1039/c6cy01051b.

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20

Purkait, Anisha, and Chandan K. Jana. "N-Aminations of Benzylamines and Alicyclic Amines with Nitrosoarenes to Hydrazones and Hydrazides." Synthesis 51, no. 13 (April 17, 2019): 2687–96. http://dx.doi.org/10.1055/s-0037-1610701.

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Unlike other alkylamines, benzylamines upon reaction with a nitrosoarene undergo oxidation to the corresponding imines. A direct amination of benzylamines, which was difficult to achieve due to its facile oxidation, to the corresponding hydrazones is reported. A wide variety of benzylamines and N-heterocycles were reacted with nitrosoarenes to provide structurally diverse hydrazones and hydrazides, respectively. Moreover, the direct N-amination reaction was applied to the one-pot synthesis of triazoles.

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21

Weber, Ariane, Linus Porthun, and Reinhard Schomäcker. "Rh-Catalyzed Reductive Amination of Undecanal in an Aqueous Microemulsion System Using a Non-Ionic Surfactant." Catalysts 11, no. 10 (October 11, 2021): 1223. http://dx.doi.org/10.3390/catal11101223.

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The homogeneously catalyzed reductive amination of the long-chain aldehyde undecanal with diethylamine was performed in an aqueous microemulsion system using the non-ionic surfactant Marlophen NP8. The experiments showed that the used water-soluble rhodium/SulfoXantphos catalyst system is suitable for this reaction. The Rh-catalyzed formation of the alcohol by-product can be completely suppressed by the use of carbon monoxide with its stabilizing effect of the catalyst system. In addition to pressure and temperature, the most important parameters for the reaction performance of the reductive amination are the concentrations of reactants. Especially, the initial concentration of the aldehyde has a strong impact on the chemoselectivity, and the formation of aldol by-product due to the fact that both, the enamine condensation and the aldol condensation are equilibrium reactions.

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22

Knochel, Paul, Andreas Steib, Sarah Fernandez, Olesya Kuzmina, Martin Corpet, and Corinne Gosmini. "Chromium(II)-Catalyzed Amination of N-Heterocyclic Chlorides with Magnesium Amides." Synlett 26, no. 08 (February 26, 2015): 1049–54. http://dx.doi.org/10.1055/s-0034-1380178.

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We report a ligand-free chromium(II)-catalyzed amination reaction of various N-heterocyclic chlorides. CrCl2 regioselectively catalyzes the reaction of chloropyridines and dichloropyridines, dichloroquinolines, dichloroisoquinolines and dichloroquinoxalines with a range of aliphatic, allylic, benzylic and saturated (hetero)cyclic magnesium amides in the presence of lithium chloride as additive. The reactions were performed at 50 °C in THF and led to the desired aminated products in 56–96% yield.

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23

Dlouhý, Jiří, and Josef Pašek. "Kinetics of hydrogenation amination of 2-propanol with aniline on a copper-chromium catalyst." Collection of Czechoslovak Chemical Communications 54, no. 2 (1989): 326–40. http://dx.doi.org/10.1135/cccc19890326.

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The kinetics of hydrogenation amination of alcohols in the liquid phase were studied in the presence of a copper(II)-chromium(III) catalyst, 2-propanol and aniline were used as the models. In addition to the kinetic investigation of the model reaction as a whole, the partial reaction steps-dehydrogenation of 2-propanol and condensation of aniline with acetone-were also examined. It was proved that, in the reaction of aniline with 2-propanol on the copper-chromium catalyst, the formation of acetone is equilibrium-controlled. The overall rate of amination of 2-propanol with aniline is determined by both the condensation of acetone with aniline and the hydrogenation of the ketimine intermediate. The amination is accelerated by addition of aluminosilicate to the copper-chromium catalyst, which confirms that the ketimine concentration is not equilibrium-controlled.

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24

Sosnovsky, George, and Klaus Purgstaller. "Aminations with O-Diphenylphosphinylhydroxylamine A Critical Evaluation." Zeitschrift für Naturforschung B 44, no. 5 (May 1, 1989): 582–86. http://dx.doi.org/10.1515/znb-1989-0514.

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A critical evaluation is presented of the scope of amination reactions with O-diphenylphosphinylhydroxylamine (ODPH) as compared to those using hydroxylamine-O-sulfonic acid (HOSA). Aminations with ODPH of isopropyl, t-butyl and cyclohexyl carbanions derived from the corresponding Grignard reagents, gave the corresponding amines in 36, 34 and 50 percent yields, respectively. The amination with HOSA of the same carbanions under similar conditions was unsuccessful. The aminative quarternization of the tertiary nitrogen of pyridine and quinoline with ODPH proceeded with comparable yields to those obtained with HOSA. An improved one flask amination with ODPH of indole, skatole and carbazole was achieved in 52-62 percent yields. The amination under the same conditions using HOSA gave consistently lower yields. Several other amination reactions which have been reported for HOSA were unsuccessful using ODPH. The conclusion is reached that overall the ODPH reagent is much less versatile than HOSA. Nevertheless, in the aminations of NH groups of heterocyclic compounds ODPH appears to be superior to HOSA and is the reagent of choice, in particular, since the preparation of ODPH is much less harzardous than that of HOSA.

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25

Salem, Mohammed A., Moustafa A. Gouda, and Ghada G. El-Bana. "Chemistry of 2-(Piperazin-1-yl) Quinoline-3-Carbaldehydes." Mini-Reviews in Organic Chemistry 19, no. 4 (June 2022): 480–95. http://dx.doi.org/10.2174/1570193x18666211001124510.

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Abstract: This review described the preparation of 2- chloroquinoline-3-carbaldehyde derivatives 18 through Vilsmeier-Haack formylation of N-arylacetamides and the use of them as a key intermediate for the preparation of 2-(piperazin-1-yl) quinoline-3-carbaldehydes. The synthesis of the 2- (piperazin-1-yl) quinolines derivatives was explained through the following chemical reactions: acylation, sulfonylation, Claisen-Schmidt condensation, 1, 3-dipolar cycloaddition, one-pot multicomponent reactions (MCRs), reductive amination, Grignard reaction and Kabachnik-Field’s reaction.

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26

Subotin, Vladyslav V., Vitalii M. Asaula, Yulian L. Lishchenko, Mykyta O. Ivanytsya, Olena O. Pariiska, Sergey V. Ryabukhin, Dmitriy M. Volochnyuk, and Sergey V. Kolotilov. "Catalytic Reductive Amination of Aromatic Aldehydes on Co-Containing Composites." Chemistry 5, no. 1 (February 17, 2023): 281–93. http://dx.doi.org/10.3390/chemistry5010022.

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The performance of a series of cobalt-based composites in catalytic amination of aromatic aldehydes by amines in the presence of hydrogen as well as hydrogenation of quinoline was studied. The composites were prepared by pyrolysis of CoII acetate, organic precursor (imidazole, 1,10-phenantroline, 1,2-diaminobenzene or melamine) deposited on aerosil (SiO2). These composites contained nanoparticles of metallic Co together with N-doped carboneous particles. Quantitative yields of the target amine in a reaction of p-methoxybenzaldehyde with n-butylamine were obtained at p(H2) = 150 bar, T = 150 °C for all composites. It was found that amination of p-methoxybenzaldehyde with n-butylamine and benzylamine at p(H2) = 100 bar, T = 100 °C led to the formation of the corresponding amines with the yields of 72–96%. In the case of diisopropylamine, amination did not occur, and p-methoxybenzyl alcohol was the sole or the major reaction product. Reaction of p-chlorobenzaldehyde with n-butylamine on the Co-containing composites at p(H2) = 100 bar, T = 100 °C resulted in the formation of N-butyl-N-p-chlorobenzylamine in 60–89% yields. Among the considered materials, the composite prepared by decomposition of CoII complex with 1,2-diaminobenzene on aerosil showed the highest yields of the target products and the best selectivity in all studied reactions.

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27

Laschat, Sabine, Philipp Seubert, Marcel Freund, Richard Rudolf, Yulin Lin, Luca Altevogt, Ursula Bilitewski, and Angelika Baro. "Buchwald–Hartwig versus Microwave-Assisted Amination of Chloroquinolines: En Route to the Pyoverdin Chromophore." Synlett 31, no. 12 (May 18, 2020): 1177–81. http://dx.doi.org/10.1055/s-0040-1707810.

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The reaction of 2-chloro-6,7-dimethoxy-3-nitroquinoline with a series of amines and aminoalkanoates under basic microwave-mediated conditions and under Buchwald–Hartwig amination conditions is reported. The microwave irradiation favored the reaction with amines, resulting in yields of up to 80%, whereas amino acid functionalization gave yields comparable to those of Buchwald–Hartwig amination. tert-Butyl (2R)-4-[(6,7-dimethoxy-3-nitroquinolin-2-yl)amino]-2-hydroxybutanoate was successfully cyclized to the pyoverdin chromophore, a subunit of siderophores.

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28

Tichá, Iveta Chena, Simona Hybelbauerová, and Jindřich Jindřich. "New α- and β-cyclodextrin derivatives with cinchona alkaloids used in asymmetric organocatalytic reactions." Beilstein Journal of Organic Chemistry 15 (April 1, 2019): 830–39. http://dx.doi.org/10.3762/bjoc.15.80.

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The preparation of new organocatalysts for asymmetric syntheses has become a key stage of enantioselective catalysis. In particular, the development of new cyclodextrin (CD)-based organocatalysts allowed to perform enantioselective reactions in water and to recycle catalysts. However, only a limited number of organocatalytic moieties and functional groups have been attached to CD scaffolds so far. Cinchona alkaloids are commonly used to catalyze a wide range of enantioselective reactions. Thus, in this study, we report the preparation of new α- and β-CD derivatives monosubstituted with cinchona alkaloids (cinchonine, cinchonidine, quinine and quinidine) on the primary rim through a CuAAC click reaction. Subsequently, permethylated analogs of these cinchona alkaloid–CD derivatives also were synthesized and the catalytic activity of all derivatives was evaluated in several enantioselective reactions, specifically in the asymmetric allylic amination (AAA), which showed a promising enantiomeric excess of up to 75% ee. Furthermore, a new disubstituted α-CD catalyst was prepared as a pure AD regioisomer and also tested in the AAA. Our results indicate that (i) the cinchona alkaloid moiety can be successfully attached to CD scaffolds through a CuAAC reaction, (ii) the permethylated cinchona alkaloid–CD catalysts showed better results than the non-methylated CDs analogues in the AAA reaction, (iii) promising enantiomeric excesses are achieved, and (iv) the disubstituted CD derivatives performed similarly to monosubstituted CDs. Therefore, these new CD derivatives with cinchona alkaloids effectively catalyze asymmetric allylic aminations and have the potential to be successfully applied in other enantioselective reactions.

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29

Cook, Ronald L., and Anthony F. Sommells. "Electrochemical Amination Reaction for Amino Acid Synthesis." Journal of The Electrochemical Society 136, no. 6 (June 1, 1989): 1845–46. http://dx.doi.org/10.1149/1.2097048.

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30

Ambethkar, Sethurajan, Muthalu Vellimalai, Vediappen Padmini, and Nattamai Bhuvanesh. "Iodine-mediated C–N and C–S bond formation: regioselective synthesis of benzo[4,5]imidazo[2,1-b]thiazoles." New Journal of Chemistry 41, no. 1 (2017): 75–80. http://dx.doi.org/10.1039/c6nj02102f.

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The regioselective synthesis of benzo[4,5]imidazo[2,1-b]thiazole derivatives via amination (C–N) and intramolecular cyclization (C–S) reactions in the presence of molecular iodine has been reported. This method is base and metal free and features inexpensive catalysts, with a simple procedure and a short reaction time.

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31

Christodoulou, Michael S., Egle M. Beccalli, and Sabrina Giofrè. "Palladium-Catalyzed Benzodiazepines Synthesis." Catalysts 10, no. 6 (June 6, 2020): 634. http://dx.doi.org/10.3390/catal10060634.

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This review is focused on palladium-catalyzed reactions as efficient strategies aimed at the synthesis of different classes of benzodiazepines. Several reaction typologies are reported including hydroamination, amination, C–H arylation, N-arylation, and the Buchwald–Hartwig reaction, depending on the different substrates identified as halogenated starting materials (activated substrates) or unactivated unsaturated systems, which then exploit Pd(0)- or Pd(II)-catalytic species. In particular, the use of the domino reactions, as intra- or intermolecular processes, are reported as an efficient and eco-compatible tool to obtain differently functionalized benzodiazepines. Different domino reaction typologies are the carboamination, aminoarylation, aminoacethoxylation, aminohalogenation, and aminoazidation.

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32

Lan, Zhou, and Yangcheng Lu. "How the substrate affects amination reaction kinetics of nitrochlorobenzene." Reaction Chemistry & Engineering 7, no. 4 (2022): 833–38. http://dx.doi.org/10.1039/d1re00534k.

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The reaction rate of the amination is affected by its electron-withdrawing group, however, there is currently a lack of quantitative research on the reaction rate of different substrates in experiments and simulations.

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33

Abdullah, N., MZ Yahya, and R. Mahmod. "Comparative study of strong anion exchange hypercrosslinked poly(HEMA-co-EGDMA-co-VBC) and strong anion exchange poly(Styrene-co-EGDMA-co-VBC): Synthesis and characterization." Chemical Engineering Research Bulletin 19 (September 10, 2017): 96. http://dx.doi.org/10.3329/cerb.v19i0.33802.

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<p>Strong anion exchange hypercrosslinked of poly(HEMA-<em>co</em>-EGDMA-<em>co</em>-VBC) (PHEV) and strong anion exchange hypercrosslinked of poly(styrene-<em>co</em>-EGDMA-<em>co</em>-VBC) (PSEV) were prepared <em>via </em>amination reaction with dimethylbutyl amine (DMBA) as the amination agent in dried toluene. The resins were characterized by SEM, FTIR, BET and elemental analysis. SEM results showed that there was no significant change of the particles shape after amination reaction for both strong anion exchange hypercrosslinked PHEV and strong anion exchange hypercrosslinked PSEV. Specific surface area (SSA) of strong anion exchange hypercrosslinked PHEV increase from 1035 m<sup>2</sup>/g to 1090 m<sup>2</sup>/g when amination reaction take place. However, SSA of strong anion exchange hypercrosslinked PHEV decreased from 124 m<sup>2</sup>/g to 27 m<sup>2</sup>/g. From FTIR spectra, significant drop occurred at 1265 cm<sup>-1</sup> band after amination reaction of strong anion exchange hypercrosslinked PSEV but SSA of strong anion exchange hypercrosslinkedPHEV showed slightly significant drop. Elemental analysis showed that nitrogen content of strong anion exchange hypercrosslinked PHEV significantly increase from 0.10% to 1.46% resulted to high IEC value. Meanwhile, nitrogen content in strong anion exchange hypercrosslinked PSEV only showed small increment in nitrogen content from 0.36% to 0.63% led to low IEC value.</p><p>Chemical Engineering Research Bulletin 19(2017) 96-101</p>

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34

Willemsen, Jorgen S., Jan C. M. van Hest, and Floris P. J. T. Rutjes. "Aqueous reductive amination using a dendritic metal catalyst in a dialysis bag." Beilstein Journal of Organic Chemistry 9 (May 17, 2013): 960–65. http://dx.doi.org/10.3762/bjoc.9.110.

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Water-soluble dendritic iridium catalysts were synthesized by attaching a reactive metal complex to DAB-Am dendrimers via an adapted asymmetric bipyridine ligand. These dendritic catalysts were applied in the aqueous reductive amination of valine while contained in a dialysis bag. Comparable conversions were observed as for the noncompartmentalized counterparts, albeit with somewhat longer reaction times. These results clearly show that the encapsulated catalyst system is suitable to successfully drive a complex reaction mixture with various equilibrium reactions to completion.

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35

Tomioka, Kiyoshi, Takeo Sakai, Tokutaro Ogata, and Yasutomo Yamamoto. "Aminolithiation of carbon-carbon double bonds as a powerful tool in organic synthesis." Pure and Applied Chemistry 81, no. 2 (January 1, 2009): 247–53. http://dx.doi.org/10.1351/pac-con-08-08-02.

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A conjugate amination of α,β-unsaturated carbonyl compounds with lithium amides has become a powerful method of N-C bond-forming reactions. Chiral ligand-controlled asymmetric version of the conjugate amination of enoates was developed for practical bench chemistry, giving the enantioenriched amination product with over 99 % ee. In situ diastereoselective alkylation of resulting lithium enolates allowed us to form vicinal N-C and C-C bonds in a one-pot operation. This protocol enabled us to realize a short-step asymmetric synthesis of otamixaban key intermediate. Treatment of product 3-benzylamino- and 3-allylaminoesters with tert-butyllithium gave five- or seven-membered lactams through [1,2]- or [2,3]-rearrangement of intermediate β-lactams. Isolated C-C double bonds were also found to accept intramolecular aminolithiation affording the corresponding hydroamination products. Chiral lithiophilic ligand-catalyzed reaction gave enantioenriched hydroamination products with high ee. Stereoselective intramolecular aminolithiation of allylaminoalkenes was coupled with subsequent carbolithiation to give doubly cyclized product amines.

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36

Mishra, Vaibhav, and Tejpal Singh Chundawat. "Pd Catalyzed N1/N4 Arylation of Piperazine for Synthesis of Drugs, Biological and Pharmaceutical Targets: An Overview of Buchwald Hartwig Amination Reaction of Piperazine in Drug Synthesis." Current Organic Synthesis 15, no. 2 (April 24, 2018): 208–20. http://dx.doi.org/10.2174/1570179415666171206151603.

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Background: Substituted piperazine heterocycles are among the most significant structural components of pharmaceuticals. N1/N4 substituted piperazine containing drugs and biological targets are ranked 3rd in the top most frequent nitrogen heterocycles in U.S. FDA approved drugs. The high demand of N1/N4 substituted piperazine containing biologically active compounds and U.S. FDA approved drugs, has prompted the development of Pd catalyzed C-N bond formation reactions for their synthesis. Buchwald-Hartwig reaction is the key tool for the synthesis of these compounds. Objective: This review provides strategies for Pd catalyzed C-N bond formation at N1/N4 of piperazine in the synthesis of drugs and biological targets with diverse use of catalyst-ligand system and reaction parameters. Conclusion: It is clear from the review that a vast amount of work has been done in the synthesis of N1/N4 substituted piperazine containing targets under the Pd catalyzed Buchwald-Hartwig amination of aryl halides by using different catalyst-ligand systems. These methods have become increasingly versatile as a result of innovation in catalyst design and improvements in reaction conditions. This review gives an overview of recent utilization of Buchwald-Hartwig amination reaction in drug/target synthesis.

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Chen, Gang, and Chun Hua Yang. "Preparation of the Gold Nanoparticles and its Activity for Single-Step Amination of Benzene to Aniline." Advanced Materials Research 661 (February 2013): 47–52. http://dx.doi.org/10.4028/www.scientific.net/amr.661.47.

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Gold nanoparticles (AuNPs) were attached to the surface of alumina particles by an in-situ immobilizing method. SEM and XPS analysis showed that the coverage of alumina particles by AuNPs increased as the amount of alumina decreased; AuNPs onto alumina particles by the conventional colloidal deposition method were also prepared, whose TEM showed that the coverage of AuNPs was evidently smaller than that in the case of modified colloidal deposition method，although the AuNPs were spread almost uniformly over the surface of alumina particles. Au-immobilized alumina particles were subsequently utilized as the catalysts for direct amination of benzene with NH3H2O as an aminating agent and H2O2 as an oxidant under mild conditions. The reaction conditions were optimized: when catalyst amount was 2.0 g, reaction temperature was 50 °C, NH3H2O amount was 60 mL, H2O2 amount was 30 mL, and reaction time is 2 h, Au-immobilized alumina particles showed the highest aniline yield (1.96 mg) for 25 mL benzene.

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38

Chen, Xin, Shuai Zhao, Zhi-Li Chen, Xue Rui, and Ming-Mei Gao. "Asymmetric Allylic Amination of Morita–Baylis–Hillman Adducts with Simple Aromatic Amines by Nucleophilic Amine Catalysis." Synlett 30, no. 06 (February 26, 2019): 703–8. http://dx.doi.org/10.1055/s-0037-1611740.

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Asymmetric allylic amination of Morita–Baylis–Hillman (MBH) adducts with simple aromatic amines is successfully realized by nucleophilic amine catalysis. A range of substituted α-methylene-β-arylamino esters is accessed in moderate to high yields (up to 88%) and with excellent enantioselectivities (up to 97% ee). Inorganic fluorides are found to be able to improve the enantioselectivity of the allylic amination reaction. A pyrrole-2-carboxylate and a cyclic imide are also compatible with this catalytic system. A chiral 2,3-dihydroquinolin-4-one derivative is easily obtained from the allylic amination product.

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39

Zhou, Houbo, Christopher M. Plummer, Huaan Li, Huahua Huang, Pengfei Ma, Le Li, Lixin Liu, and Yongming Chen. "Regioselective post-functionalization of isotactic polypropylene by amination in the presence of N-hydroxyphthalimide." Polymer Chemistry 10, no. 5 (2019): 619–26. http://dx.doi.org/10.1039/c8py01344f.

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40

Михайлов, Степан Петрович, Валентин Юрьевич Долуда, Михаил Геннадьевич Сульман, and Валентина Геннадьевна Матвеева. "CURRENT STATES OF REGENERATIVE AMINATION." Вестник Тверского государственного университета. Серия: Химия, no. 1(47) (April 5, 2022): 24–36. http://dx.doi.org/10.26456/vtchem2022.1.2.

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Процесс восстановительного аминирования лежит в основе полученная различных ценных химических веществ. Одним из важных классов таких химикатов являются N-содержащие функциональные соединения, которые можно применять в качестве исходного материала или растворителя для синтеза фармацевтических препаратов и агрохимикатов. В последние годы было проведено множество исследований по поиску наиболее активного и селективного гетерогенного катализатора реакции восстановительного аминирования. Настоящая обзорная статья посвящена изучению каталитического поведения различных гетерогенных катализаторов при восстановительном аминировании левулиновой кислоты и ее производного. Было проведено сравнение выходов пирролидона при аналогичных условиях реакции. В обзоре также рассматривалось проведение исследуемой реакции как в реакторах периодического действия, так и в проточных реакторах непрерывного действия. The process of reductive amination underlies the production of various valuable chemicals. One important class of such chemicals are N-containing functional compounds that can be used as a starting material or solvent for the synthesis of pharmaceuticals and agrochemicals. In recent years, many studies have been carried out to find the most active and selective heterogeneous catalyst for the reductive amination reaction. This review article is devoted to the study of the catalytic behavior of various heterogeneous catalysts in the reductive amination of levulinic acid and its derivative. The yields of pyrrolidone were compared under similar reaction conditions. The review also considered the performance of the reaction under study both in batch reactors and in continuous flow reactors.

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41

Zhu, Shihao, Keran Chen, and Xinrui Zhou. "Photocatalytic C-N addition amination of olefin." E3S Web of Conferences 213 (2020): 01007. http://dx.doi.org/10.1051/e3sconf/202021301007.

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Amines widely exist in nature, wherein some of cyclic amines have crucially biological and physiological activities. They are also the basic blocks for the syntheses of important intermediates, raw materials or fine chemicals such as pharmaceuticals, pesticides and dyes. Amine synthesis by photocatalytic amination of phthalimide and olefins using porphyrin iron (III) or phthalocyanine iron(II) as photosensitizer was investigated in this paper. The results showed that the reactions selectively developed C-N addition and generated a series of compounds containing benzazepine structure with the highest yield of 99.0% at 30 °C. The scope of substrates was further examined and the results demonstrated that the reaction was effective to various olefins, especially to aliphatic olefins. In addition, the influence of the light source was further investigated. The simple, low-power, insect trap lamp (6 W, 365 nm) was used as the light source for the reaction, and a high yield of 95.0% was obtained. Therefore, the inspiring results provide a green and efficient method for the synthesis of compounds containing benzazepine structure.

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42

Mahato, Shreya, Parveen Rawal, Ajitrao Kisan Devadkar, Mayank Joshi, Angshuman Roy Choudhury, Bhaskar Biswas, Puneet Gupta, and Tarun K. Panda. "Hydroboration and reductive amination of ketones and aldehydes with HBpin by a bench stable Pd(ii)-catalyst." Organic & Biomolecular Chemistry 20, no. 5 (2022): 1103–11. http://dx.doi.org/10.1039/d1ob02339j.

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A Pd(ii) complex catalysed hydroboration and reductive amination reaction of several aldehydes and ketones are reported. DFT-based computational study of the reaction mechanism unravels the dual role of HBpin in accomplishing the hydroboration reaction.

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43

Cai, Chun, and Ru-Shuang Zhou. "C–H Amination of Nitro Azaheterocyclic Compounds by Vicarious Nucleophilic Substitution." Synlett 33, no. 01 (October 19, 2021): 88–92. http://dx.doi.org/10.1055/a-1672-7285.

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AbstractVarious nitro azaheterocyclic compounds were subjected to C–H amination by vicarious nucleophilic substitution with 4H-1,2,4-triazol-4-amine (ATA). The aminated products were characterized by NMR, mass spectroscopy, and single-crystal X-ray diffraction analyses. The substrates examined gave moderate to excellent yields (30–88%) and showed good regioselectivities. This protocol offers the advantages of mild conditions, a short reaction time (2–4 hours), and an inexpensive, commercially available, and less-toxic amination reagent; moreover, no additional catalyst or reagent is needed. A possible reaction mechanism is discussed.

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44

Osipova, Elena Yu, Alexey N. Rodionov, Alexander A. Simenel, Yury A. Belousov, Oleg M. Nikitin, and Vadim V. Kachala. "Application of reductive amination reaction for preparation of ferrocene-modified porphyrins." Journal of Porphyrins and Phthalocyanines 16, no. 11 (October 22, 2012): 1225–32. http://dx.doi.org/10.1142/s1088424612501246.

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Porphyrin-modified ferrocenes were synthesized via the reductive amination reaction of ferrocenylpyrazolecarboxaldehydes and tetraphenylporphyrinamine. The steric hindrance of ferrocene moiety was found to play the key role in this reaction.

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45

Borges da Silva, Ramon, Rodolfo Inêz Teixeira, James L. Wardell, Solange M. S. V. Wardell, and Simon J. Garden. "Copper(ii) catalyzed synthesis of novel helical luminescent benzo[4,5]imidazo[1,2-a][1,10]phenanthrolines via an intramolecular C–H amination reaction." Organic & Biomolecular Chemistry 15, no. 4 (2017): 812–26. http://dx.doi.org/10.1039/c6ob02508k.

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46

Heshmatpour, Felora, and Reza Abazari. "Formation of dispersed palladium–nickel bimetallic nanoparticles in microemulsions: synthesis, characterization, and their use as efficient heterogeneous recyclable catalysts for the amination reactions of aryl chlorides under mild conditions." RSC Adv. 4, no. 99 (2014): 55815–26. http://dx.doi.org/10.1039/c4ra06958g.

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47

Goh, Jeffrey, Seng Kheong Ong, Yan Sheng Tan, and Teck-Peng Loh. "Catalyst-free C–N bond formation under biocompatible reaction conditions." Green Chemistry 24, no. 8 (2022): 3321–25. http://dx.doi.org/10.1039/d2gc00027j.

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A C–N bond formation reaction under benign conditions for the amination of allenic ketones to access enaminones is reported. This reaction is atom economical, green, highly regioselective and works well with many structurally crucial amines.

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48

Kalita, Surajit, Sason Shaik, and Kshatresh Dutta Dubey. "MD simulations and QM/MM calculations reveal the key mechanistic elements which are responsible for the efficient C–H amination reaction performed by a bioengineered P450 enzyme." Chemical Science 12, no. 43 (2021): 14507–18. http://dx.doi.org/10.1039/d1sc03489h.

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49

Guyon, Carole, Eric Da Silva, Romain Lafon, Estelle Métay, and Marc Lemaire. "Reductive amination using a combination of CaH2 and noble metal." RSC Advances 5, no. 3 (2015): 2292–98. http://dx.doi.org/10.1039/c4ra14808h.

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50

Gu, Jiajia, Zheng Fang, Chengkou Liu, Xin Li, Ping Wei, and Kai Guo. "Direct oxidative amination of aromatic aldehydes with amines in a continuous flow system using a metal-free catalyst." RSC Advances 6, no. 76 (2016): 72121–26. http://dx.doi.org/10.1039/c6ra16240a.

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