Direct hydroxyethylation of amines by carbohydrates via ruthenium catalysis

2019 ◽  
Vol 21 (11) ◽  
pp. 3127-3132 ◽  
Author(s):  
Le Jia ◽  
Mohamed Makha ◽  
Chen-Xia Du ◽  
Zheng-Jun Quan ◽  
Xi-Cun Wang ◽  
...  
Keyword(s):  
Aromatic Amines ◽  
Amino Alcohols ◽  
Ruthenium Catalysis ◽  
Halogen Free ◽  
First Time

A halogen-free catalytic methodology for the synthesis of β-amino alcohols from aromatic amines and biomass-related carbohydrates is demonstrated for the first time.

scholarly journals Efficient N-formylation of primary aromatic amines using novel solid acid magnetic nanocatalyst

RSC Advances ◽  
2020 ◽  
Vol 10 (67) ◽  
pp. 41229-41236
Author(s):  
Jitendra Kumar Yadav ◽  
Priyanka Yadav ◽  
Satish K. Awasthi ◽  
Alka Agarwal
Keyword(s):  
Magnetic Nanoparticles ◽  
Aromatic Amines ◽  
Sulfonic Acid ◽  
Solid Acid ◽  
Recyclable Catalyst ◽  
Primary Amines ◽  
Magnetic Nanocatalyst ◽  
Reaction Conditions ◽  
Primary Aromatic Amines ◽  
First Time

Sulfonic acid functionalized over biguanidine fabricated silica-coated heterogeneous magnetic nanoparticles (NP@SO3H) have been synthesized, well characterized and explored for the first time, as an efficient and recyclable catalyst for N-formylation of primary amines under mild reaction conditions.

scholarly journals Two Different Quinohemoprotein Amine Dehydrogenases Initiate Anaerobic Degradation of Aromatic Amines inAromatoleum aromaticumEbN1

2019 ◽  
Vol 201 (16) ◽  
Author(s):  
Georg Schmitt ◽  
Martin Saft ◽  
Fabian Arndt ◽  
Jörg Kahnt ◽  
Johann Heider
Keyword(s):  
Aromatic Amines ◽  
Catalytic Efficiency ◽  
Growth Conditions ◽  
Complete Replacement ◽  
Content Type ◽  
Enzyme Family ◽  
First Time ◽  
Α Subunits ◽  
Substrate Spectrum

ABSTRACTAromatic amines like 2-phenylethylamine (2-PEA) and benzylamine (BAm) have been identified as novel growth substrates of the betaproteobacteriumAromatoleum aromaticumEbN1, which degrades a wide variety of aromatic compounds in the absence of oxygen under denitrifying growth conditions. The catabolic pathway of these amines was identified, starting with their oxidative deamination to the corresponding aldehydes, which are then further degraded via the enzymes of the phenylalanine or benzyl alcohol metabolic pathways. Two different periplasmic quinohemoprotein amine dehydrogenases involved in 2-PEA or BAm metabolism were identified and characterized. Both enzymes consist of three subunits, contain two hemeccofactors in their α-subunits, and exhibit extensive processing of their γ-subunits, generating four intramolecular thioether bonds and a cysteine tryptophylquinone (CTQ) cofactor. One of the enzymes was present in cells grown with 2-PEA or other substrates, showed an α2β2γ2composition, and had a rather broad substrate spectrum, which included 2-PEA, BAm, tyramine, and 1-butylamine. In contrast, the other enzyme was specifically induced in BAm-grown cells, showing an αβγ composition and activity only with BAm and 2-PEA. Since the former enzyme showed the highest catalytic efficiency with 2-PEA and the latter with BAm, they were designated 2-PEADH and benzylamine dehydrogenase (BAmDH). The catalytic properties and inhibition patterns of 2-PEADH and BAmDH showed considerable differences and were compared to previously characterized quinohemoproteins of the same enzyme family.IMPORTANCEThe known substrate spectrum ofA. aromaticumEbN1 is expanded toward aromatic amines, which are metabolized as sole substrates coupled to denitrification. The characterization of the two quinohemoprotein isoenzymes involved in degrading either 2-PEA or BAm expands the knowledge of this enzyme family and establishes for the first time that the necessary maturation of their quinoid CTQ cofactors does not require the presence of molecular oxygen. Moreover, the study revealed a highly interesting regulatory phenomenon, suggesting that growth with BAm leads to a complete replacement of 2-PEADH by BAmDH, which has considerably different catalytic and inhibition properties.

scholarly journals Anhydrous Titanium(III) chloride as a New Lewis-Acid Catalyst for Ring Opening of Epoxides with Aromatic Amines

2007 ◽  
Vol 2 (2) ◽  
pp. 1934578X0700200
Author(s):  
Suchitra Bhatt ◽  
Sandip K. Nayak
Keyword(s):  
Ambient Temperature ◽  
Lewis Acid ◽  
Aromatic Amines ◽  
Ring Opening ◽  
Acid Catalyst ◽  
Amino Alcohols ◽  
Azide Ion ◽  
Ring Opening Of Epoxides ◽  
Lewis Acid Catalyst

Anhydrous titanium(III) chloride was found to be a simple and efficient Lewis acid catalyst for ring opening of epoxides at ambient temperature. The reaction proceeded smoothly with anilines as well as azide ion as nucleophiles to give the corresponding β-amino alcohols and β-azido alcohols in moderate to good yields.

Rhodium-catalyzed aminohydroxylation of unactivated alkenes in aqueous media for the benign synthesis of 1,2-amino alcohols

2019 ◽  
Vol 21 (4) ◽  
pp. 780-784 ◽  
Author(s):  
Yufeng Shi ◽  
Yufan Wang ◽  
Xunbo Lu ◽  
Yulong Zhang ◽  
Yuzhou Wu ◽  
...  
Keyword(s):  
Aqueous Media ◽  
Amino Alcohols ◽  
Benign Synthesis ◽  
First Time

An efficient catalytic aminohydroxylation reaction of alkenes in aqueous media is disclosed for the first time.

scholarly journals Asymmetric ring-opening reaction of meso-epoxides with aromatic amines using homochiral metal–organic frameworks as recyclable heterogeneous catalysts

RSC Advances ◽  
2018 ◽  
Vol 8 (49) ◽  
pp. 28139-28146 ◽  
Author(s):  
Koichi Tanaka ◽  
Maya Kinoshita ◽  
Jun Kayahara ◽  
Yutaro Uebayashi ◽  
Kazusada Nakaji ◽  
...  
Keyword(s):  
Aromatic Amines ◽  
Ring Opening ◽  
Heterogeneous Catalysts ◽  
Metal Organic Framework ◽  
Metal Organic Frameworks ◽  
Amino Alcohols ◽  
Ring Opening Reaction ◽  
Ring Opening Reactions ◽  
Metal Organic ◽  
Asymmetric Ring Opening

Asymmetric ring-opening reactions of meso-epoxides by aromatic amines were achieved by using some chiral metal–organic frameworks. The corresponding β-amino alcohols were obtained with good yields and enantioselectivities (up to 97% ee).

Catalyst Free, Nitromethane Assisted Facile Ring Opening of Epoxide with Less Reactive Aromatic Amines

2020 ◽  
Author(s):  
Sumit Kumar ◽  
Meenakshi Bansal ◽  
Charu Upadhyay ◽  
Maria Grishina ◽  
Vladimir Potemkin ◽  
...  
Keyword(s):  
Aromatic Amines ◽  
Ring Opening ◽  
Spectroscopic Studies ◽  
Bioactive Scaffolds ◽  
Chemistry Research ◽  
Ring Opening Reactions ◽  
Ring Opening Of Epoxide ◽  
Sterically Hindered ◽  
First Time ◽  
Nucleophilic Ring Opening

<p>Nucleophilic ring opening reactions of epoxides with aromatic amines are in the forefront of the synthetic organic chemistry research to build new bioactive scaffolds. Here, a convenient, green and highly efficient regioselective ring opening of sterically hindered (2R,3S)-3-(<i>N</i>-Boc-amino)-1-oxirane-4-phenylbutane with various poorly reactive aromatic amines are accomplished under microwave irradiation in nitromethane. All the reactions effectively implemented for various aromatic amines involves reuse of nitromethane that supports its dual role as a solvent and catalyst. The corresponding new β-alcohol analogs of hydroxyethylamine (HEA) are isolated in 41-98% yields. The reactions proceed under mild conditions for a broad range of less reactive and sterically hindered aromatic amines. Proton NMR and UV-visible spectroscopic studies suggest that the nucleophilicity of amines is influenced by nitromethane, which is substantiated by the extensive computational studies. Overall, this methodology elucidates the first time use of nitromethane as a solvent for the ring opening reactions under microwave conditions involving equimolar ratio of epoxide and aromatic amine without any catalyst, facile ring opening of complex epoxide by less reactive aromatic amines, low reaction time, less energy consumption, recycling of the solvent and simple workup procedures.</p>

scholarly journals Insights into Ag(i)-catalyzed addition reactions of amino alcohols to electron-deficient olefins: competing mechanisms, role of catalyst, and origin of chemoselectivity

RSC Advances ◽  
2018 ◽  
Vol 8 (70) ◽  
pp. 40338-40346 ◽  
Author(s):  
Chunhui Liu ◽  
Peilin Han ◽  
Zhizhong Xie ◽  
Zhihong Xu ◽  
Donghui Wei
Keyword(s):  
Amino Alcohols ◽  
Addition Reactions ◽  
First Time

The origin of the chemoselectivities of Ag(i)-catalyzed addition reactions of amino alcohols to olefin has been predicted for the first time.

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