37904-94-2Relevant academic research and scientific papers
Preparation of β-aminoketone by 2,3-dichloro-5,6-dicyanobenzoquinone catalysed three-component Mannich reaction
Xu, Feng,Li, Peng-Bo,Tian, You-Ping,Li, Hui-Li,Li, Qi
, p. 15 - 18 (2010)
2,3-Dichloro-5,6-dicyanobenzoquinone (DDQ) was used as an effi cient catalysts for a one-pot, three-component Mannich reaction of cyclohexanone or acetophenone with aromatic aldehydes and aromatic amines under solvent free condition. This protocol has the advantage of high yield, mild reaction conditions, lower catalyst loading and simple work up procedure.
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.
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
Air-stable Organoantimony (III) Perfluoroalkyl(aryl)sulfonate complexes as highly efficient, selective, and recyclable catalysts for C–C and C–N bond-forming reactions
Fan, Qi,Guo, Rui,Li, Ningbo,Ma, Rong,Qiao, Jie,Xu, Li,Xu, Shitang,Xu, Xinhua,Yun, Kemin
, (2021/07/08)
A series of air-stable organoantimony (III) perfluoroalkyl(aryl)sulfonate complexes with an azastibocine framework {t-BuN(CH2C6H4)2SbOSO2C4F9 (2a); [t-BuN(CH2C6/
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.
Hf(OTf)4 as a highly potent catalyst for the synthesis of Mannich bases under solvent-free conditions
Gong, Shan-Shan,Han, Shuai-Bo,Liu, Rong,Peng, Xiao-Chong,Sun, Qi,Wei, Jing-Ying
, (2020/01/28)
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.
Ultrasonic-assisted green synthesis of β-amino carbonyl compounds by copper oxide nanoparticles decorated phosphate functionalized graphene oxide via Mannich reaction
Achary, L. Satish K.,Nayak, Pratap S.,Barik, Bapun,Kumar, Aniket,Dash, Priyabrat
, p. 137 - 147 (2019/09/03)
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 viaa 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), N2 adsorption-desorption measurements, X-ray photoelectron spectroscopy (XPS) analysis, Ammonia temperature programmed desorption analysis (NH3-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 Cu2+ species and minor reduction of oxygen functional groups on GO. A higher surface area of 162 m2/g for CuO/PGO was found from N2 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 NH3-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 Br?nsted 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.
Dehydrogenation and α-functionalization of secondary amines by visible-light-mediated catalysis
Bujok, Robert,Morawska, Paulina,Pawlowski, Robert,Stanek, Filip,Stodulski, Maciej
, p. 2103 - 2112 (2020/03/27)
A visible-light-mediated process for dehydrogenation of amines has been described. The given protocol showed a broad substrate scope, mild reaction conditions and excellent results without the requirement of tedious purification. This process can be applied in one-pot functionalization of secondary amines with various nucleophiles through the cooperation of visible-light and Lewis acid catalysis, leading to the structurally varied essential components of biologically active molecules. In addition, Stern-Volmer studies and quenching experiments revealed the role of a catalyst and led to the proposed mechanism of this transformation.
