Preparation of 5-(Aminomethyl)-2-furanmethanol by direct reductive amination of 5-Hydroxymethylfurfural with aqueous ammonia over the Ni/SBA-15 catalyst

2018 ◽  
Vol 93 (10) ◽  
pp. 3028-3034 ◽  
Author(s):  
Wei Chen ◽  
Yong Sun ◽  
Juan Du ◽  
Zhihao Si ◽  
Xing Tang ◽  
...  
Keyword(s):  
Reductive Amination ◽  
Aqueous Ammonia

Electrochemical synthesis of amino acids by reductive amination of keto acids. I. Reduction at mercury electrodes

1978 ◽  
Vol 31 (1) ◽  
pp. 73 ◽  
Author(s):  
EA Jeffery ◽  
A Meisters
Keyword(s):  
Reductive Amination ◽  
Phenylacetic Acid ◽  
Reduction Potential ◽  
Aqueous Ammonia ◽  
Saturated Calomel Electrode ◽  
Mercury Electrode ◽  
Ammonia Concentration ◽  
Initial Current ◽  
Keto Acids ◽  
Mercury Electrodes

Racemic 2-amino-2-phenylacetic acid, monoammonium glutamate, 2-aminobutyric acid, α-alanine and ammonium 5-amino-5-phenylvalerate have been prepared by electrochemical reductive amination of the corresponding keto acids in aqueous ammonia/ammonium chloride solution at a mercury electrode. The yields ranged from 24% for ammonium 5-amino-5-phenylvalerate to 88% for 2-amino-2-phenylacetic acid. The current efficiency and yield of 2-amino-2-phenylacetic acid from reductive amination of 2-oxo-2-phenylacetic acid increased with increase in ammonia concentration. Also, decreasing the reduction potential from -1.10 to -1.30 V (with respect to a saturated calomel electrode) in 2 M ammonia raised the initial current density from c. 2 mA/cm2 to c. 7 mA/cm2 but halved the yield of 2-amino-2-phenylacetic acid.

Microwave-Assisted Reductive Amination with Aqueous Ammonia: Sustainable Pathway Using Recyclable Magnetic Nickel-Based Nanocatalyst

2019 ◽  
Vol 7 (6) ◽  
pp. 5963-5974 ◽  
Author(s):  
Maela Manzoli ◽  
Emanuela Calcio Gaudino ◽  
Giancarlo Cravotto ◽  
Silvia Tabasso ◽  
R. B. Nasir Baig ◽  
...  
Keyword(s):  
Reductive Amination ◽  
Aqueous Ammonia ◽  
Microwave Assisted

Reductive amination of furfural to furfurylamine using aqueous ammonia solution and molecular hydrogen: an environmentally friendly approach

2016 ◽  
Vol 18 (2) ◽  
pp. 487-496 ◽  
Author(s):  
Maya Chatterjee ◽  
Takayuki Ishizaka ◽  
Hajime Kawanami
Keyword(s):  
Molecular Hydrogen ◽  
Reductive Amination ◽  
Aqueous Ammonia ◽  
Environmentally Friendly ◽  
Ammonia Solution ◽  
High Yield ◽  
Aqueous Ammonia Solution ◽  
Reaction Condition ◽  
Environmentally Friendly Approach ◽  
Very High

An efficient process was developed to obtain furfurylamine with very high yield (∼92%) through the reductive amination of furfural under a mild reaction condition.

CONJUGATED OESTROGENS. I

1963 ◽  
Vol 43 (3) ◽  
pp. 345-360 ◽  
Author(s):  
Stanley Kushinsky ◽  
Jane (Wu) Tang
Keyword(s):  
Molecular Weight ◽  
Formic Acid ◽  
Ethyl Acetate ◽  
High Molecular Weight ◽  
Secondary Amine ◽  
Aqueous Ammonia ◽  
Organic Solution ◽  
Extraneous Material

ABSTRACT A convenient and mild procedure is described in this paper whereby free and conjugated oestrogens may be extracted from urine. The extracts containing approximately 90 per cent of the oestrogens are devoid of most of the extraneous material and may be reduced in volume to less than 1/15 of that of the urine. The procedure consists of the following steps: (1) a 10 per cent (v/v) solution of a high molecular weight secondary amine (Amberlite LA-2, Rohm and Haas) in ethyl acetate is washed with formic acid and water, (2) the oestrogens in urine (acidified to pH 2 or 3 with H2SO4) are extracted with the LA-2 solution, (3) the oestrogen fraction is back-extracted from the organic solution with dilute aqueous ammonia.

Selective Functionalization at N2-Position of Guanine in Oligonucleotides via Reductive Amination

2020 ◽  
Author(s):  
Bapurao Bhoge ◽  
Ishu Saraogi
Keyword(s):  
Organic Chemistry ◽  
Chemical Biology ◽  
Reductive Amination ◽  
The Other ◽  
Dna Oligomers ◽  
Site Specific ◽  
Wide Applicability ◽  
Dna Oligonucleotides ◽  
Selective Functionalization

Chemo- and site-specific modifications in oligonucleotides have wide applicability as mechanistic probes in chemical biology. Here we have employed a classical reaction in organic chemistry, reductive amination, to selectively functionalize the N<sup>2</sup>-amine of guanine/2’-deoxyguanine monophosphate. This method specifically modifies guanine in several tested DNA oligonucleotides, while leaving the other bases unaffected. Using this approach, we have successfully incorporated desired handles chemoselectively into DNA oligomers.

Bringing Biocatalysis into the Deuteration Toolbox

2019 ◽  
Author(s):  
Jack Rowbotham ◽  
Oliver Lenz ◽  
Holly Reeve ◽  
Kylie Vincent
Keyword(s):  
Late Stage ◽  
Hydrogen Isotope ◽  
Reductive Amination ◽  
Mechanistic Studies ◽  
Ambient Conditions ◽  
Synthetic Pathway ◽  
Drug Candidates ◽  
Isotopic Selectivity ◽  
Reducing Equivalents

<p></p><p>Chemicals labelled with the heavy hydrogen isotope deuterium (<sup>2</sup>H) have long been used in chemical and biochemical mechanistic studies, spectroscopy, and as analytical tracers. More recently, demonstration of selectively deuterated drug candidates that exhibit advantageous pharmacological traits has spurred innovations in metal-catalysed <sup>2</sup>H insertion at targeted sites, but asymmetric deuteration remains a key challenge. Here we demonstrate an easy-to-implement biocatalytic deuteration strategy, achieving high chemo-, enantio- and isotopic selectivity, requiring only <sup>2</sup>H<sub>2</sub>O (D<sub>2</sub>O) and unlabelled dihydrogen under ambient conditions. The vast library of enzymes established for NADH-dependent C=O, C=C, and C=N bond reductions have yet to appear in the toolbox of commonly employed <sup>2</sup>H-labelling techniques due to requirements for suitable deuterated reducing equivalents. By facilitating transfer of deuterium atoms from <sup>2</sup>H<sub>2</sub>O solvent to NAD<sup>+</sup>, with H<sub>2</sub> gas as a clean reductant, we open up biocatalysis for asymmetric reductive deuteration as part of a synthetic pathway or in late stage functionalisation. We demonstrate enantioselective deuteration via ketone and alkene reductions and reductive amination, as well as exquisite chemo-control for deuteration of compounds with multiple unsaturated sites.</p><p></p>

Mild Temperature Copper-Catalyzed Amination of Aryl Halides with Aqueous Ammonia in the Presence of Pyridyldiketone Ligands

2019 ◽  
Author(s):  
Racha Abed Ali Abdine ◽  
Anna Walczak ◽  
Sultan Abu A Aeash ◽  
Gracjan Kurpik ◽  
Artur R. Stefankiewicz ◽  
...  
Keyword(s):  
Catalytic System ◽  
Aqueous Ammonia ◽  
Aryl Halides ◽  
Efficient Coupling ◽  
Ambidentate Ligand ◽  
Mild Temperature

Ambidentate ligand pyridyldiketones were used in combination with copper to catalyze maintain of aryl halides under very mild temperatures. This novel catalytic system allow efficient coupling in one of the smoothest conditions ever reported in literature.

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