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• 106291-87-6 C₂₈H₂₄N₂ 

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Relevant academic research and scientific papers

Cerium chloride (CeCl3·7H2O) as a highly efficient catalyst for one-pot three-component Mannich reaction

We have demonstrated the use of CeCl3·7H2O as highly efficient catalyst for one-pot threecomponent Mannich reaction to afford β-amino carbonyl compounds in good to excellent yield within shorter period of reaction time. The process is mild, efficient, environmentally benign with the use of little amount of catalyst.

Mechanistic studies on counter-ionic effects of camphorsulfonate-based ionic liquids on kinetics, thermodynamics and stereoselectivity of β-amino carbonyl compounds

Catalysis is important in various applications of organic chemistry and its output product control for stereoselective compounds is outrageous. Establishment of experimental facts of stereoselective compounds from catalysis and their validation using theoretical evidences is the key to understand various mechanisms of optically active compounds. A family of new ionic liquids (ILs) with various imidazolium cations and camphorsulfonate anion as environmentally benign liquid salts have been synthesized and deployed for catalysis of β-amino carbonyl compounds. The products were formed using ILs as a homogeneous catalyst with excellent product yield and diastereoselectivity. The effect of counter ions, Hammett acidity and viscosity of ILs along with solvent and temperature are explored in terms of reaction kinetics and product yields. Density functional theory (DFT) was used to investigate thermodynamical study of mechanistic pathway of the reaction. The DFT calculations predicted that the catalysis mechanism involved both counterions of the IL. Moreover, it is evidenced that the syn-pathway required lower activation energy while anti-pathway led to thermodynamically stable product. This study explores new avenues for using ILs as potential homogeneous catalysts for the production of stereoselective species.

Ionic liquid-immobilized proline(s) organocatalyst-catalyzed one-pot multi-component Mannich reaction under solvent-free condition

A highly efficient clean and simple methodology has been established for the one-pot Mannich reaction using ionic liquid-immobilized proline(s) organocatalyst under solvent-free conditions. The three components comprising substituted acetophenones, substituted aromatic aldehydes and substituted aromatic amines underwent Mannich reactions in the presence of 7?mol% of ionic liquid-immobilized proline(s) organocatalyst to provide β-amino carbonyl compounds in 2–3?h at room temperature with excellent yields. This methodology provides several advantages such as mild reaction conditions, short reaction time, low catalyst loading percentage, multi-component approach, transition metal-free and solvent-free synthesis. The ionic liquid-immobilized proline(s) organocatalyst was recycled and reused five times without a significant loss of its catalytic activity.

Hf(OTf)4 as a highly potent catalyst for the synthesis of Mannich bases under solvent-free conditions

Hf(OTf)4 was identified as a highly potent catalyst (0.1–0.5 mol%) for three-component Mannich reaction under solvent-free conditions. Hf(OTf)4-catalyzed Mannich reaction exhibited excellent regioselectivity and diastereoselectivity when alkyl ketones were employed as substrates. 1H NMR tracing of the H/D exchange reaction of ketones in MeOH-d4 indicated that Hf(OTf)4 could significantly promote the keto-enol tautomerization, thereby contributing to the acceleration of reaction rate.

Br?nsted-Lewis dual acidic ionic liquid immobilized on mesoporous silica materials as an efficient cooperative catalyst for Mannich reactions

Novel mesoporous silica supported ILs have been prepared and successfully applied as a heterogeneous catalyst in Mannich reactions. The excellent recyclability of the supported catalyst, mild reaction conditions, good to excellent yields, low catalyst loading, and operational simplicity are the important features of this methodology.

Choline-based biodegradable ionic liquid catalyst for Mannich-type reaction

A three-component Mannich-type reaction of aromatic aldehydes, ketones, and amines was catalyzed by a novel choline-based acidic ionic liquid. The proposed catalyst was a Lewis-Br?nsted dual acid catalyst as well as water-tolerant. The β-amino carbonyl compounds were obtained at room temperature in reasonable to good yields ranging from 63 to 98%. After the reaction, the catalyst could be recycled and reused for 5 times without obvious decrease of the yield. Further, the catalyst was environment-friendly with a significant biodegradation rate. [Figure not available: see fulltext.]

Ultrasound-promoted synthesis of-Amino carbonyl compounds via a mannich reaction catalyzed by ionic liquids

Background: Mannich reaction is one of the most important carbon-carbon bond formation reactions in organic synthesis. Traditional methods require a large amount of ungreen catalysts or much longer reaction time, which limits the scope of their application. So, a recyclable catalyst with high activity and selectivity is highly appreciated, and the highly shortened reaction time is also very appealing. Methods: An efficient and facile process to prepare a series of -Amino carbonyl compounds was found via Mannich reactions catalyzed by caprolactam-based Br?nsted acidic ionic liquids under ultrasonic irradiation. Results: [Capl][BF4] was the most effective catalyst in the Mannich reaction, and good yields was gained within 2-6 h. The activity and stability of the catalyst was maintained very well even after five times, and ultrasound can effectively shorten the reaction time and enhance the yield at ambient condition. Conclusion: A convenient procedure for Mannich reaction using acidic ILs catalyst under ultrasonic irradiation has been designed with many superiorities, such as simple manipulation, less reaction time and high yields. The Mannich reaction takes place in no presence of organic solvents such as toluene or ethanol, etc. The new synthetic method reported in this paper would make appreciable contribution to the subject of environmental friendly chemistry and it is available for industrial applications.

A magnetic solid sulfonic acid modified with hydrophobic regulators: An efficient recyclable heterogeneous catalyst for one-pot aza-Michael-type and Mannich-type reactions of aldehydes, ketones, and amines

Two convenient green protocols for the synthesis of β-amino ketones have been developed which involve one-pot aza-Michael-type and Mannich-type reactions of a series of aldehydes, ketones, and amines in the presence of a catalytic amount of the magnetic solid sulfonic acid catalyst, Fe3O4@SiO2@Me&Et-PhSO3H, at room temperature. The catalyst can be reused four times without loss of activity.

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

Rice-husk-supported FeCl3 nano-particles (FeCl3-RiH) were prepared and used as an environmentally friendly catalyst in the synthesis of b-amino carbonyl compounds, 1,8- dioxo-octahydro xanthenes, and bis-indolyl methanes from simple and readily available precursor molecules.

Nafion-H: A recyclable and diastereoselective solid acid catalyst for three-component mannich reaction

One-pot, three-component Mannich reactions of ketones, aldehydes and amines are efficiently catalyzed by heterogeneous Nafion-H at ambient temperature to give the corresponding β-amino ketones compounds in good to excellent yields. The catalyst can be easily recovered and reused without any decrease of activity for at least four times. Diastereoselective products can be obtained in Mannich reaction of aliphatic ketone. Pleiades Publishing, Ltd., 2012.