804-20-6Relevant academic research and scientific papers
Synthesis of β-Amino Ketones using graphene oxide: a benign carbonaceous acid catalyst for Mannich reaction
Saravana Ganesan, Nagappan,Suresh, Palaniswamy
, p. 1197 - 1210 (2021/01/07)
Abstract: Simple and easily preparable graphene oxide (GO) is used as a straightforward carbocatalyst for the synthesis of β-amino ketones via a 3-component Mannich reaction under mild condition. The native GO is acting as a carbonaceous solid Br?nsted acid catalyst without any special functionalization, yielding a spectrum of β-amino ketones under metal-free conditions. The present catalytic method offers a benign and simple procedure without any hazardous workup, and chromatographic purification resulted in an excellent yield of β-amino ketones. The catalyst has shown good sustainability up to 6 consecutive catalytic cycles without any significant loss in its activity. The stability of the recovered catalyst is proved by analytical techniques such as FT-IR, PXRD, SEM, and TEM. This mild solid-acid catalyst offers an alternative and sustainable approach to get synthetically essential β-amino ketones under greener conditions. Graphical abstract: [Figure not available: see fulltext.].
A ZnS@N-GQD nanocomposite as a highly effective and easily retrievable catalyst for the sonosynthesis of β-amino carbonyls
Mutashar, Mohammaed Abdulridha,Safaei-Ghomi, Javad,Saharkhan, Zahra
, p. 19935 - 19942 (2021/06/16)
A three-component reaction of acetophenone, aromatic aldehydes, and aniline derivatives has been achieved in the presence of a ZnS@nitrogen graphene quantum dot (N-GQD) nanocomposite as a highly effective heterogeneous catalyst to produce β-amino carbonyls. The catalyst has been characterized by XRD, SEM, TEM, FT-IR spectroscopy, EDS, BET and TGA techniques. The feasibility of carrying out the one-pot synthesis under ultrasonic irradiation with a heterogeneous nanocatalyst could improve the reaction rates and shorten the reaction times.
Ionic liquid-immobilized proline(s) organocatalyst-catalyzed one-pot multi-component Mannich reaction under solvent-free condition
Prabhakara,Maiti, Barnali
, p. 2381 - 2401 (2020/01/31)
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.
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
Rahmatpour, Ali,Eeimen, Reza,Goodarzi, Niloofar
, p. 2915 - 2930 (2019/08/30)
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.
Cellulose-Supported Ionic Liquid Phase Catalyst-Mediated Mannich Reaction
Khanapure, Sharanabasappa,Jagadale, Megha,Kale, Dolly,Gajare, Shivanand,Rashinkar, Gajanan
, p. 513 - 523 (2019/05/15)
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.
An Efficient Synthesis of 1,3-Diphenyl-3-phenylamino-propan-1-one and its Derivatives by Mannich Reaction in the Presence of Doped Porous Carbon by Nitrogen and Sulfur (NS-PCS) as Catalyst
Mansoori, Aida,Eshghi, Hossein,Lari, Jalil
, p. 548 - 553 (2017/12/28)
Synthesis of β-amino carbonyl compounds by Mannich reaction involves the creation of various bonds in a single action and is attracting great attention as one of the most powerful synthetic tools for the expansion of molecular convolution and versatility. Carbon spheres (CSs) combine the advantages of carbon materials with spherical colloids, which gives them several inimitable features as catalysts. In this work, the reaction between acetophenone, aromatic aldehydes, and aromatic amines has been efficiently catalyzed by porous carbon spheres which were doped by nitrogen and sulfur (NS-PCS) at ambient temperature to give diverse β-amino carbonyl compounds in nearly high yields.
Synthesis of [beta]-amino ketone compounds through catalysis by bifunctional ionic liquid
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Paragraph 0039; 0040, (2017/05/18)
The invention discloses a synthesis method of [beta]-amino ketone compounds through catalysis by a bifunctional ionic liquid. A key of the technical scheme is that the bifunctional ionic liquid having bifunctional groups of Bronsted acid and Lewis acid is employed as a catalyst while water/ethanol are employed as a reaction medium. Raw materials, including aromatic aldehyde, ketone and aromatic amine, are subjected to a reaction at normal temperature and under normal pressure to obtain a target product. The synthesis method has the advantages of: 1) the raw materials are widely-sourced and the compounds are easy to prepare; 2) the catalyst has bifunctional groups, wherein the Bronsted acid and the Lewis acid in the molecule achieve synergistic catalysis, and the catalyst can be recycled, thereby achieving significant energy-saving and emission-reducing effects; and 3) the synthesis method is carried out with the water/ethanol as the reaction medium, so that the method has safe and stable reactions, is easy to industrially amplify and is an environment-friendly chemical engineering process.
Ultrasound-promoted synthesis of-Amino carbonyl compounds via a mannich reaction catalyzed by ionic liquids
Qian, Hua,Kai, Wang,Zhen, Juejie
, p. 143 - 147 (2016/03/01)
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.
Mesoporous silica nanoparticles (MSNs) as an efficient and reusable nanocatalyst for synthesis of β-amino ketones through one-pot three-component Mannich reactions
Nasresfahani, Zahra,Kassaee, Mohammad Zaman,Nejati-Shendi, Mohammad,Eidi, Esmaiel,Taheri, Qazale
, p. 32183 - 32188 (2016/04/26)
Mesoporous silica nanoparticles (MSNs) proved efficient and reusable in the catalytic synthesis of β-amino ketones, through three-component Mannich reaction of ketones, aromatic aldehydes and aromatic amines under solvent-free conditions. Simple reaction conditions coupled with simple work-ups, makes this methodology a superior option for the synthesis of such β-amino ketones.
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
Movassagh, Barahman,Tahershamsi, Leili,Mobaraki, Akbar
, p. 1851 - 1854 (2015/03/30)
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.
