Synthesis Of Β-amino Carbonyl Compounds Research Articles

Hen egg white lysozyme encapsulated in ZIF-8 for performing promiscuous enzymatic Mannich reaction

Hen egg white lysozyme (HEWL) was exploited for the synthesis of β-amino carbonyl compounds through a direct and three-component Mannich reaction in aqueous, confirming high chemoselectivity toward imine. In order to further extend the applications of the enzyme, HEWL was encapsulated using a metal-organic framework (MOF). The reactivity, stereoselectivity, and reusability of the encapsulated enzyme were investigated. The reaction was significantly enhanced as compared to the non-encapsulated enzyme. A mutated version of the enzyme, containing Asp52Ala (D52A), lacking important catalytical residue, has lost the bacterial site activity against Micrococcus luteus (M. luteus) while the D52A variant displayed an increased rate of the Mannich reaction, indicating a different catalytical residue involved in the promiscuous reaction. Based on site-directed mutagenesis, molecular docking, and molecular dynamic studies, it was proposed that π-stacking, H-bond interactions, and the presence of water in the active site may play crucial roles in the mechanism of the reaction.

One-pot synthesis of β-amino carbonyl compounds under solvent free condition by using alum doped nanopolyaniline catalyst

Alum doped nanopolyaniline (NDPANI), an efficient and reusable green catalyst for synthesis of β-amino carbonyl compounds has been developed. Mannich type reaction of various amines, aldehydes and ketones is carried out to synthesize the desire β-amino carbonyl compounds with excellent yield under solvent free condition. The advantages of this catalyst are inexpensive, reusability, easy preparation and stable. The reaction condition represents an advanced over established method in terms of avoiding solvent, mild reaction condition, clean reaction profile and simple workup.

Organocatalytic enantioselective one-pot synthesis of β-aminoketones via Mannich reaction

An effective protocol for the asymmetric synthesis of β-amino carbonyl compounds using pyrrolidine based organocatalyst has been developed via one-pot three-component Mannich reaction. The organocatalyst (S)-N-(2,4-dinitrophenyl) pyrrolidine-2-carboxamide 3b confirmed to be the superior organocatalyst in solvent acetonitrile to obtain corresponding products in up to 89% yield and with excellent ee (90%). This organocatalytic reaction reveals productive result with a range of other aldehydes. Aromatic aldehydes having electron withdrawing substituent show the best results. Excellent yields, high enantioselectivity, mild reaction condition, and simple experimental work-up procedure are some of the advantages of this method.

Titanium tetrachloride incorporated crosslinked polystyrene copolymer as an efficient and recyclable polymeric Lewis acid catalyst for the synthesis of Β-amino carbonyl compounds at room temperature

An efficient and eco-friendly procedure for one-pot synthesis of β-amino carbonyl compounds by three-component reaction of aromatic aldehydes, acetophenone, and aromatic amines via a Mannich type reaction using a stable tightly bound complex, titanium tetrachloride incorporated crosslinked polystyrene copolymer (PS/TiCl4), as a water tolerant, recoverable, and reusable polymeric Lewis acid catalyst in ethanol at room temperature is reported. The complex of the polystyrene and TiCl4 provides a shelf-stable acidic, water tolerant material, and it is not easily hydrolyzed by water. Our findings thus show a novel and improved modification of the Mannich type reaction in terms of mild reaction conditions, clean reaction profiles, applicability to various substrates using a simple workup procedure which makes this reaction an interesting alternative to previously applied procedures. The recyclability of the catalyst makes this protocol environmentally benign.

Ultrasonic-assisted green synthesis of β-amino carbonyl compounds by copper oxide nanoparticles decorated phosphate functionalized graphene oxide via Mannich reaction

Highly efficient and active CuO nanoparticle decorated Phosphate functionalised graphene oxide (PGO-CuO) nanocomposite has been synthesized in a water-isopropanol system and used as an active catalyst for the synthesis of β-amino carbonyl compounds via Mannich reaction by using a greener ultrasonic method. • CuO nanoparticles were decorated on PGO via a simple wet chemical synthetic route. • PGO-CuO catalyst was thoroughly characterized by various analytical techniques. • A greener ultrasonic route was used for synthesis of β-amino carbonyl compounds. • Higher catalytic efficiency was obtained under solventless condition. • The catalyst could be recycled for six times without any effective loss in activity. A facile chemical synthetic route has been demonstrated for the synthesis of copper oxide nanoparticles decorated phosphate functionalized graphene oxide (CuO/PGO). The synthesized nanocatalyst was used as an efficient and active candidate for the synthesis of β-amino carbonyl compounds via a green synthetic ultrasonic route. The structural properties of the samples were investigated by means of a number of sophisticated techniques like X-ray diffraction (XRD), Fourier-transform Infrared (FTIR) spectroscopy, High Resolution Transmission Electron Microscope (HRTEM), N 2 adsorption-desorption measurements, X-ray photoelectron spectroscopy (XPS) analysis, Ammonia temperature programmed desorption analysis (NH 3 -TPD) and Raman spectroscopy. HRTEM analysis confirmed the presence of spherical CuO nanoparticles distributed uniformly throughout the PGO surface. XPS analysis demonstrated the presence of Cu 2+ species and minor reduction of oxygen functional groups on GO. A higher surface area of 162 m 2 /g for CuO/PGO was found from N 2 adsorption-desorption isotherms. Later on, the presence of acidic groups on CuO/PGO that play an essential role in the catalytic activity was examined by NH 3 -TPD and pyridine adsorbed IR analysis. The total acidity on the surface of synthesized nanocatalyst was found to be of 0.59 mmol g −1 which includes both Lewis as well as Brönsted acidic sites. A higher product yield of 95% in a shorter period of time of 15 min was achieved which is superior to many reported catalytic systems. A combined strategy involving greener and easier ultrasonic route and use of an efficient acidic graphene oxide-based catalyst resulted in higher catalytic activity and stability with good recyclability.

Cellulose-Supported Ionic Liquid Phase Catalyst-Mediated Mannich Reaction

Cellulose-supported ionic liquid phase (SILP) catalyst containing a camphor sulfonate anion with a pendant ferrocenyl group was prepared and characterised with different analytical techniques such as Fourier-transform infrared, Fourier-transform Raman, and cross polarization–magic angle spinning (CP-MAS) 13C NMR spectroscopy, X-ray diffraction, scanning electron microscopy, and thermogravimetric analysis. The SILP catalyst displayed excellent catalytic activity in the synthesis of β-amino carbonyl compounds by Mannich reaction. Recycling studies revealed that SILP catalyst could be reused six times without significant decrease in catalytic activity.

Tartaric Acid–Zinc Nitrate as an Efficient Brønsted Acid-Assisted Lewis Acid Catalyst for the Mannich Reaction

Tartaric acid–zinc nitrate has been found to be an efficient Brønsted acid-assisted Lewis acid catalytic system for the facile synthesis of β-amino carbonyl compounds through the one-pot Mannich reaction of aldehydes, aromatic amines and ketones in ethanol at room temperature. Remarkable enhancement of reactivity by tartaric acid (Brønsted acid) was observed in these reactions in the presence of anhydrous zinc nitrate (Lewis acid), due to coordination of the tartaric acid ligand to zinc ions increasing the acidity of the system. This procedure shows some advantages such as mild reaction conditions, short reaction times and high yields.

Green composite nanostructure (Fe3O4@PEG-SO3H): Preparation, characterization and catalytic performance in the efficient synthesis of [formula omitted]-amino carbonyl compounds at room temperature

The synthesis of a few biologically active β-amino carbonyl compounds via Mannich three-component reaction by using poly(ethylene glycol) (PEG)-SO3H-functionalized Fe3O4 is described. The Fe3O4@PEG-SO3H nanocomposite was synthesized via in-situ co-precipitation method and characterized by Fourier transform infrared (FT-IR) spectroscopy, field-emission scanning electron microscopy (FE-SEM) and transmission electron microscopy (TEM) images, X-ray diffraction (XRD) pattern, energy-dispersive X-ray (EDX), vibrating sample magnetometer (VSM), N2 adsorption–desorption by Brunauer–Emmett–Teller (BET), thermogravimetric analysis (TGA) and inductively coupled plasma (ICP) analyses. Furthermore, this is the first report on using of the green heterogeneous nanocomposite catalyst in the one-pot multicomponent synthesis of β-amino carbonyl compounds at room temperature. This synthesized nanocatalyst can be easily recovered from the reaction mixture by using an external magnet and reused for several times without significant decrease in catalytic activity.

Three-component carbon-carbon bond-forming reactions for the synthesis of β-amino carbonyl compounds using maleic acid-catalyzed one-pot mannich-type reaction in ethanol

Three-component carbon-carbon bond-forming reactions for the synthesis of β-amino carbonyl compounds using maleic acid-catalyzed one-pot mannich-type reaction in ethanol

Design and development of a novel magnetic camphor nanospheres core/shell nanostructure

In this work, the first synthesis, characterization and catalytic performance of Fe3O4/camphor core/shell nanospheres as a magnetic composite nanocatalyst were reported. The characterization was carried out by Fourier transform infrared spectroscopy, field-emission scanning electron microscopy, transmission electron microscopy, X-ray diffraction, energy-dispersive X-ray spectroscopy, thermogravimetric analysis, vibrating sample magnetometer, N2 adsorption–desorption by Brunauer–Emmett–Teller and inductively coupled plasma analyses. The recoverable heterogeneous nanostructure catalyst was simply prepared and effectively employed in the one-pot multicomponent synthesis of β-amino carbonyl compounds in ethanol as a green solvent at room temperature. Further advantages of this new protocol are short reaction times, high yields, easy workup procedure, inexpensive and eco-friendly protocol and magnetically recoverability and several times reusability of the nanocatalyst without significant decrease in catalytic activity.

Design of Supported Organocatalysts from Carboxylic Acids for the Mannich-Type Synthesis of β-Amino Carbonyl Compounds

New supported acidic organocatalysts were prepared by the impregnation of three carboxylic acids (CF3COOH, CCl3COOH, and CH3COOH) on silica support at room temperature in diethyl ether. The catalysts were characterized by scanning electron microscopy, energy dispersion X-ray analysis (EDX), Brunauer-Emmett-Teller-surface-area-analysis (BET), thermogravitational analysis, Fourier transform infrared, and powder X-ray diffractometry analysis. These solid acids were observed as highly efficient reusable catalysts at room temperature for the selective synthesis of β-amino carbonyl compounds via Mannich-type reactions of acetophenone, arylamine and arylaldehydes using two different conditions in CH2Cl2 solution and solvent-free grinding within a short time. The more acidic two catalysts could be recycled for up to five cycles with a small loss in catalytic activity.

One-pot synthesis of β-amino carbonyl compounds catalyzed silica supported phenylphosphinic acid

AbstractA simple and facile synthesis of β-amino carbonyl compounds was developed by the one-pot condensation of cyclohexanone, aromatic aldehydes and anilines at 25°C in the presence of silica supported phenylphosphinic acid. β-Amino carbonyl compounds were obtained in moderate to good yields and reasonable diastereoselectivities. This method has the advantages of short reaction time, mild reaction conditions, reusable catalyst, cost efficiency and environment friendly. In addition, acetophenone and aliphatic ketones as reactants were investigated.

Mesoporous silica polymer nanocomposites encapsulated with polyphosphoric acid for the synthesis of β-amino carbonyl compounds under environmental benign conditions

Hydrophobic polymer functionalized SBA-15 was impregnated with polyphosphoric acid. Polymer composites SAR displays a crucial role in the selective synthesis of Mannich base.

Aqueous formic acid: an efficient, inexpensive and environmentally friendly catalyst for diastereoselective synthesis of β-amino carbonyl derivatives

In this article, we present a convenient and green method for synthesis of β-amino carbonyl compounds through ball-milling technique by using aqueous formic acid, which is an inexpensive and highly efficient catalyst. This multi-component reaction was done at room temperature with high anti-selectivity and easy workup. The use of solvent-free ball-milling technique helped to have high yields and more cleanness, besides omitting the need for solvent in this method.

Diastereoselective three-component synthesis of β-amino carbonyl compounds using diazo compounds, boranes, and acyl imines under catalyst-free conditions.

Diazo compounds, boranes, and acyl imines undergo a three-component Mannich condensation reaction under catalyst-free conditions to give the anti β-amino carbonyl compounds in high diastereoselectivity. The reaction tolerates a variety of functional groups, and an asymmetric variant was achieved using the (−)-phenylmenthol as chiral auxiliary in good yield and selectivity. These β-amino carbonyl compounds are valuable intermediates, which can be transformed to many potential bioactive molecules.

A facile synthesis of β-amino carbonyl compounds through an aza-Michael addition reaction under solvent-free conditions

An efficient and eco-friendly process for the synthesis of β-amino carbonyl compounds was introduced in this paper. The oxanorbornene β-amino esters and β-enamine esters were successfully prepared from oxabornene and amines by using solvent-free aza-Michael addition reaction in the absence of any catalyst. Oxanorbornene β-amino esters were the major product at room temperature, but higher temperature (e.g. 90 °C) led to the formation of β-enamine esters. In addition, all of the target compounds were characterized by IR, 1H NMR, 13C NMR, and HR-MS. A possible reaction pathway was also proposed.

PPh3-catalyzed Mannich reaction: a facile one-pot synthesis of β-amino carbonyl compounds under solvent-free conditions at room temperature

PPh3 was used as an efficient catalyst for the one-pot three-component Mannich reactions of acetophenone with different aromatic amines and aromatic aldehydes under solvent-free conditions at room temperature. This method provides a novel and improved method for preparing β-amino carbonyl compounds in the absence of acidic catalyst in excellent yield. Little catalyst loading, easy accessibility of the catalyst, mild conditions, and simple work-up procedure are the main features of this protocol.

Sulfonated poly(4-vinylpyridine) heteropolyacid salts: A reusable green solid catalyst for Mannich reaction

Sulfonated poly(4-vinylpyridine) heteropolyacid salts acted as a heterogeneous catalyst to effectively catalyze the one-pot synthesis of β-amino carbonyl compounds via the Mannich reaction between aromatic aldehydes, aromatic ketone, and aromatic amines. In addition, the catalyst could be easily recovered by the filtration and reused six times without significant loss of catalytic activity.

Rice-husk-supported FeCl3 nano-particles: Introduction of a mild, efficient and reusable catalyst for some of the multi-component reactions

Abstract Rice-husk-supported FeCl 3 nano-particles (FeCl 3 –RiH) were prepared and used as an environmentally friendly catalyst in the synthesis of β-amino carbonyl compounds, 1,8-dioxo-octahydro xanthenes, and bis-indolyl methanes from simple and readily available precursor molecules.

Aza-Michael reaction promoted by aqueous sodium carbonate solution

A general and efficient aza-Michael reaction promoted by aqueous sodium carbonate solution has been developed. The reaction has complete mono-alkylation selectivity and proceeds with complete chirality retention for chiral amino esters. With a broad substrate scope, a well-common catalyst and simple operation, the catalytic approach provides a facile, practicable, economical, and environmentally benign method for the synthesis of β-amino carbonyl compounds.