1075-76-9Relevant articles and documents
β-Cyclodextrin promoted aza-Michael addition of amines to conjugated alkenes in water
Surendra,Krishnaveni, N. Srilakshmi,Sridhar,Rao, K. Rama
, p. 2125 - 2127 (2006)
Highly efficient and environmentally benign aza-Michael additions of amines to α,β-unsaturated compounds catalyzed by β-cyclodextrin in water to produce the corresponding β-amino compounds in excellent yields under mild conditions are described. β-Cyclodextrin can be recovered and reused in subsequent reactions without loss of activity.
Aza-Michael reactions in water using functionalized ionic liquids as the recyclable catalysts
Liu,Lu,Gu,Lu
, p. 775 - 781 (2011)
Some recyclable SO3H-functionalized ionic liquids have been used as catalysts in water for the aza-Michael reactions of amines with α,β-unsaturated compounds to produce β-amino compounds. High yields of the products, short reaction times, mild reaction conditions, simple experimental procedure, reusable catalysts and no obvious loss of the catalytic activity make this protocol a contribution to organic chemistry.
A catalytic method for room-temperature Michael additions using 12-tungstophosphoric acid as a reusable catalyst in water
Chen, Xiang,She, Jin,Shang, Zhicai,Wu, Jun,Zhang, Peizhi
, p. 3931 - 3936 (2008)
12-Tungstophosphoric acid (H3PW12O40) has been found to be an efficient and recyclable catalyst in promoting room temperature Michael additions of amines and aryl thiols to α,β- unsaturated esters and acrylonitrile in water to afford the corresponding saturated amines in good to excellent yields. Georg Thieme Verlag Stuttgart.
Indium trichloride-catalyzed conjugate addition of amines to α,β-ethylenic compounds in water
Loh, Teck-Peng,Wei, Lin-Li
, p. 975 - 976 (1998)
Catalytic amount of indium (III) trichloride efficiently catalyzed Michael reaction between amines and α,β-ethylenic compounds in water and under mild conditions. Indium trichloride can be recovered and reused without decrease in yield.
Air- and moisture-stable cationic (diphosphine)palladium(II) complexes as hydroamination catalysts X-ray crystal structures of two complexes
Li, Kelin,Horton, Peter N.,Hursthouse, Michael B.,Hii, King Kuok Mimi
, p. 250 - 257 (2003)
A series of cationic (diphosphine)palladium(II) complexes have been prepared and fully characterized, including two crystal structures. These complexes were evaluated as catalysts for the hydroamination of acyclic alkenes. The reactivity of the catalysts is dependent on the nature of the diphosphine ligand and the substituents on the amine and alkene substrates.
Green synthesis of CuO nanoparticles using: Lantana camara flower extract and their potential catalytic activity towards the aza-Michael reaction
Chowdhury, Rakesh,Khan, Aslam,Rashid, Md. Harunar
, p. 14374 - 14385 (2020)
Aza-Michael addition is one of the most exploited reactions in organic chemistry. It is regarded as one of the most popular and efficient methods for the creation of the carbon-nitrogen bond, which is a key feature of many bioactive molecules. Herein, we report the synthesis of CuO nanoparticles by an alkaline hydrolysis process in the presence of the flower extract of Lantana camara, an invasive weed, followed by calcination in air at 400 °C. Microscopic results indicated that the plant extract played an important role in the modulation of the size and shape of the product. In the presence of extract, porous CuO nanostructures are formed. While mostly aggregated rod-shaped CuO nanostructures are formed in the absence of extract. The products are pure and highly crystalline possessing the monoclinic phase. The CuO nanoparticles have been used as a catalyst in the aza-Michael addition reaction in aqueous medium under ultrasound vibration. The product yield is excellent and the catalyst is reusable up to the fifth cycle. The catalyst system can be extended to various substituted substrates with excellent to moderate yields.
Solid sodium stannate as a high-efficiency superbase catalyst for anti-Markovnikov hydroamination and hydroalkoxylation of electron-deficient olefins under mild conditions
Zhang, Shuguo,Wei, Yudan,Yin, Shuangfeng,Au, Chak-Tong
, p. 712 - 716 (2011)
A solid superbase with H- above 26.5 has been obtained through thermal treatment of sodium stannate hydrate. It was found to be an efficient catalyst for anti-Markovnikov hydroamination and hydroalkoxylation of electron-deficient olefins under mild conditions.
Functionalized ionic liquid promoted aza-michael addition of aromatic amines
Liu, Xiao-Bing,Lu, Ming,Lu, Ting-Ting,Gu, Guo-Liang
, p. 1221 - 1226 (2010)
A functionalized ionic liquid, 3-(N,N-dimethyldodecylammonium) propanesulfonic acid hydrogen sulphate ([DDPA][HSO4]) has been used as catalyst for the aza-Michael reactions of aromatic amines with α,β-unsaturated compounds at room temperature to produce β-amino compounds in good yields. The catalyst can be reused for several times without obvious loss of the catalytic activity.
TiCl2(OTf)-SiO2: A solid stable lewis acid catalyst for Michael addition of α-Aminophosphonates, Amines, Indoles and Pyrrole
Firouzabadi, Habib,Iranpoor, Naser,Farahi, Soghra
, p. 317 - 323 (2018)
TiCl2(OTf)-SiO2 is simply prepared by immobilization of TiCl3(OTf) on silica gel surface and introduced as a non-hygroscopic Lewis acid catalyst for C-N and C-C bond formation via Michael addition reaction. A variety of structurally diverse nitrogen nucleophiles including α-aminophosphonates, aliphatic and aromatic amines and imidazole were evaluated as Michael donors. Friedel–Crafts alkylation of indoles and pyrrole was also investigated through Michael addition reaction in the presence of TiCl2(OTf)-SiO2 as a catalyst. The reactions were conducted at room temperature or 60 °C under solvent-free conditions and the desired Michael adducts were obtained in high to excellent yields.
Synthesis and Catalytic Application of Mixed Valence Iron (FeII/FeIII)-Based OMS-MIL-100(Fe) as an Efficient Green Catalyst for the aza-Michael Reaction
Rostamnia, Sadegh,Alamgholiloo, Hassan
, p. 2918 - 2928 (2018)
Abstract: In the present study, open metal site iron-based MOF [MIL-100(Fe)], by a solvothermal method with polygonal morphology, are synthesised and then applied as a heterogeneous green catalyst for aza-Michael addition of various amines with α, β-unsaturated compounds. The MIL-100(Fe) was found to be efficient, selective, green and heterogeneous catalyst for the aza-Michael reaction. The proposed catalyst has better recyclability and can be reused six times without apparent loss of activity. Graphical Abstract: [Figure not available: see fulltext.].
