802-49-3Relevant 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.].
Tuning Microenvironment of Quaternary Ammonium Salt and Tertiary Amine Bifunctionalized Polyacrylonitrile Fiber for Cooperatively Catalyzed Aza-Michael Addition
Yuan, Xueyu,Du, Huimin,Zhao, Jingyan,Chima, Anyaegbu Ejike,Ma, Ning,Tao, Minli,Zhang, Wenqin
, p. 832 - 843 (2020/08/10)
A series of novel polyacrylonitrile fiber catalysts modified with different ratio of quaternary ammonium salt (QA) to tertiary amine (TA) were screened for heterogeneously catalyzed aza-Michael addition in water. The best catalyst was found to be PAN
Graphene oxide as a catalyst for one-pot sequential aldol coupling/aza-Michael addition of amines to chalcones through in situ generation of Michael acceptors under neat conditions
Khalili, Dariush,Lavian, Salime,Moayyed, Mohammadesmaeil
, (2019/12/25)
Graphene oxide (GO) in conjunction with tetra n-butyl ammonium bromide (TBAB) was found to function as an efficient catalyst for one-pot sequential aldol coupling/aza-Michael addition of amines to chalcones in a single reaction vessel. Benzaldehydes and acetophenone were coupled in situ to produce their corresponding chalcones which underwent a subsequent aza-Michael addition under solvent-free condition. This procedure avoids the use of precious metals and the heterogeneous nature of the GO simplifies purification and isolation of the products by simple filtration of the catalyst.
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.
An uncommon use of irradiated flavins: Br?nsted acid catalysis
Arakawa, Yukihiro,Mihara, Tomohiro,Fujii, Hiroki,Minagawa, Keiji,Imada, Yasushi
supporting information, p. 5661 - 5664 (2020/06/09)
We present that thioacetalization of aldehydes can be induced by blue light irradiation in the presence of a catalytic amount of riboflavin tetraacetate (RFTA) under aerobic conditions. Several control experiments have suggested that the reaction is more
Design, and facile synthesis of 1,3 diaryl-3-(arylamino)propan-1-one derivatives as the potential alpha-amylase inhibitors and antioxidants
Bashary, Roqia,Khatik, Gopal L.
, p. 156 - 162 (2018/10/20)
Diabetes is the most prevalent metabolic disorder causing a high rate of mortality and morbidity. Recently alpha-amylase is reported to be good drug design target for the treatment of diabetes mellitus. We have designed 116 molecules based on aza-Michael
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.
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.
Br?nsted-Lewis dual acidic ionic liquid immobilized on mesoporous silica materials as an efficient cooperative catalyst for Mannich reactions
Wang, Hong Bo,Yao, Nan,Wang, Long,Hu, Yu Lin
supporting information, p. 10528 - 10531 (2017/10/03)
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.
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.
