4151-04-6Relevant articles and documents
Dolomite (CaMg(CO3)2) as a recyclable natural catalyst in Henry, Knoevenagel, and Michael reactions
Tamaddon, Fatemeh,Tayefi, Mohammad,Hosseini, Elaheh,Zare, Elham
, p. 36 - 42 (2013/02/22)
Iranian dolomite (CaMg(CO3)2) which consists of double-layered carbonates with Ca2+ and Mg2+ ions was utilized as a heterogeneous base catalyst in the CC, CN, and CS bond forming reactions via the Henry, Knoevenagel, aza-Michael, and thia-Michael transformations under mild conditions in water. Iranian dolomite has been characterized by X-ray diffraction (XRD), Fourier transform infrared spectroscopy (FT-IR), Brunauer Emmett Teller (BET) and XRF chemical analysis, while its basic strength was evaluated by following the Hammett indicators procedure. This water-insoluble natural catalyst demonstrated high activity and was reusable.
Lipase-catalyzed aza-michael reaction on acrylate derivatives
Steunenberg, Peter,Sijm, Maarten,Zuilhof, Han,Sanders, Johan P. M.,Scott, Elinor L.,Franssen, Maurice C. R.
, p. 3802 - 3813 (2013/06/05)
A methodology has been developed for an efficient and selective lipase-catalyzed aza-Michael reaction of various amines (primary and secondary) with a series of acrylates and alkylacrylates. Reaction parameters were tuned, and under the optimal conditions it was found that Pseudomonas stutzeri lipase and Chromobacterium viscosum lipase showed the highest selectivity for the aza-Michael addition to substituted alkyl acrylates. For the first time also, some CLEAs were examined that showed a comparable or higher selectivity and yield than the free enzymes and other formulations.
Aza-michael addition of amines to α,β-unsaturated compounds using molecular iodine as catalyst
Borah, Kalyan Jyoti,Phukan, Mridula,Borah, Ruli
experimental part, p. 2830 - 2836 (2010/11/02)
Aza-Michael adducts are obtained in very good yields by the conjugate addition of aliphatic amines to α,β-unsaturated compounds using molecular iodine as catalyst in dichloromethane at room temperature. Aromatic amines were found to be reactive under reflux in toluene.
Silicon tetrachloride catalyzed aza-michael addition of amines to conjugated alkenes under solvent-free conditions
Azizi, Najmedin,Baghi, Roya,Ghafuri, Hossein,Bolourtchian, Mohammad,Hashemi, Mohammad
experimental part, p. 379 - 382 (2010/04/03)
The efficient and very simple conjugate addition of aromatic and aliphatic amines to α,β-unsaturated carbonyl compounds under solvent-free conditions in the presence of catalytic amount of silicon tetrachloride is reported. The reaction of aryl and alkyl amines with different Michael acceptors gave the corresponding Michael adducts with simple catalyst and good to excellent yields. Georg Thieme Verlag Stuttgart New York.
Microwave-assisted, rapid, solvent-free aza-michael reaction by perchloric acid impregnated on silica gel
Singh, Surya Prakash,Kumar, T. Vijaya,Chandrasekharam,Giribabu,Reddy, P. Yella
experimental part, p. 3982 - 3989 (2009/12/24)
Highly efficient solvent-free aza-Michael additions of a variety of amines to,-unsaturated carbonyl compounds under microwave-irradiation conditions catalyzed by perchloric acid impregnated on silica gel (HClO4/SiO2) is reported. The reactions are completed within 2-7min in a microwave oven to produce the corresponding adducts in excellent yields, and the catalyst can be recovered and reused.
A basic ionic liquid as catalyst and reaction medium: A rapid and simple procedure for Aza-Michael addition reactions
Xu, Jian-Ming,Wu, Qi,Zhang, Qing-Yi,Zhang, Fu,Lin, Xian-Fu
, p. 1798 - 1802 (2008/02/08)
A fast, mild, and quantitative procedure for Michael addition reactions between various amines and α,β-unsaturated carbonyl compounds and nitriles in the presence of an easily accessible basic ionic liquid - 3-butyl-1-methylimidazolium hydroxide, [bmIm]OH - as both catalyst and reaction medium has been developed. For large-scale reactions the products could be directly distilled from the ionic liquid, allowing the use of organic solvents to be avoided totally. The ionic liquid could be reused at least eight times with consistent activity and was stable during the reaction process. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU)-promoted efficient and versatile aza-Michael addition
Yeom, Chang-Eun,Kim, Mi Jeong,Kim, B. Moon
, p. 904 - 909 (2007/10/03)
A convenient and versatile method was developed for aza-Michael addition using a substoichiometric amount of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). Various nitrogen nucleophiles were efficiently introduced to α,β-unsaturated carbonyl compounds employing 0.5 equiv of DBU. Furthermore, other heteroatomic nucleophiles could also be introduced successfully under the same reaction conditions.
Cellulose-supported copper(0) catalyst for aza-Michael addition
Reddy, K. Rajender,Kumar, Nadakudity S.
, p. 2246 - 2250 (2007/10/03)
Cellulose-supported copper(0) efficiently catalyzes the aza-Michael reaction of N-nucleophiles, such as amines and imidazoles with α,β-unsaturated compounds to produce the corresponding β-amino compounds and N-substituted imidazoles in excellent yields. The reactions are facile and the recovered catalyst is used for several cycles with consistent activity. Georg Thieme Verlag Stuttgart.
ZrOCl2·8H2O on montmorillonite K10 accelerated conjugate addition of amines to α,β-unsaturated alkenes under solvent-free conditions
Hashemi, Mohammed M.,Eftekhari-Sis, Bagher,Abdollahifar, Amir,Khalili, Behzad
, p. 672 - 677 (2007/10/03)
At room temperature, ZrOCl2·8H2O on montmorillonite K10 efficiently catalyzes conjugate addition of amines to a variety of conjugated alkenes such as α,β-unsaturated carbonyl compounds, carboxylic esters, nitriles and amides under solvent-free conditions. The catalyst can be recycled for subsequent reactions without any appreciable loss of efficiency.
Boric acid: A novel and safe catalyst for aza-Michael reactions in water
Chaudhuri, Mihir K.,Hussain, Sahid,Kantam, M. Lakshmi,Neelima
, p. 8329 - 8331 (2007/10/03)
Boric acid efficiently catalyzes the conjugate addition of aliphatic amines to α,β-unsaturated compounds to produce β-amino compounds, with great alacrity and excellent yields, in water under mild conditions. Aromatic amines do not participate effectively in the reaction.
