30539-20-9Relevant academic research and scientific papers
On-water magnetic NiFe2O4 nanoparticle-catalyzed Michael additions of active methylene compounds, aromatic/aliphatic amines, alcohols and thiols to conjugated alkenes
Payra, Soumen,Saha, Arijit,Banerjee, Subhash
, p. 95951 - 95956 (2016/10/25)
Here, we have demonstrated the Michael addition of active methylene compounds, aromatic/aliphatic amines, thiols and alcohols to conjugated alkenes using magnetic nano-NiFe2O4 as reusable catalyst in water. Nano-NiFe2O4 efficiently catalyzed the formation of C-C and C-X (X = N, S, O etc.) bond through 1,4-addition reactions.
MgO nanoparticles as an efficient and reusable catalyst for aza-Michael reaction
Tajbakhsh, Mahmood,Farhang, Maryam,Hosseini, Ali Asghar
, p. 665 - 672 (2014/05/20)
MgO nanoparticles were prepared by an improved sol-gel technique which appeared to have narrow size distributions. The synthesized magnesium oxide nanoparticles were used as an efficient catalyst in aza-Michael reaction for addition of amines to a series of α,β-unsaturated carbonyl compounds and nitro olefins under solvent-free conditions at room temperature to afford high yields of the β-amino carbonyl and β-nitro amines. The catalyst can be recovered and reused at least five successive runs without loss of activity. Graphical abstract: [Figure not available: see fulltext.]
Selective and nonselective aza-michael additions catalyzed by a chiral zirconium bis-diketiminate complex
El-Zoghbi, Ibrahim,Kebdani, Myriam,Whitehorne, Todd J. J.,Schaper, Frank
, p. 6986 - 6995 (2014/01/06)
Reaction of the chiral bis-diketiminate complex rac- or (R,R)-C 6H10(nacnacXyl)2ZrCl2 with AgOTf yielded the corresponding bis-triflate complex. The complex geometry changes from distorted octahedral in the dichloride complex to a pseudotetrahedral coordination involving π coordination of the diketiminate ligands. The bis-triflate complex is highly active for aza-Michael additions with turnover frequencies of 20000/h for the addition of morpholine to acrylonitrile and 1000/h for the addition of morpholine to methacrylonitrile. The enantioselectivities of the latter reaction in various solvents were low, never surpassing 19% ee. The reaction is first-order in olefin concentration and second order in amine concentration, which is explained by its participation as a base in the reaction mechanism. The presence of catalytic amounts of triethylamine slightly increases the observed rate constants and reduces the reaction order in amine to first order. Other activated alkenes such as methacrylonitrile, crotonitrile, methyl acrylate, and cyclohexenone can be employed, but no reactivity is observed toward styrene or vinyl ethers. Primary amines, secondary amines, and anilines can be employed as nucleophiles with activities correlating with their nucleophilicity, but the catalyst is unstable in the presence of alcohols.
Ultrasound-assisted aza-Michael reaction in water: A green procedure
Bandyopadhyay, Debasish,Mukherjee, Sanghamitra,Turrubiartes, Luis C.,Banik, Bimal K.
experimental part, p. 969 - 973 (2012/05/20)
The conjugate addition of amines to conjugated alkenes (commonly known as aza-Michael reaction) constitutes a key step for the synthesis of various complex natural products, antibiotics, α-amino alcohols and chiral auxiliaries. Ultrasound-induced addition of several amines to α, β-unsaturated ketones, esters and nitriles has been carried out very efficiently in water as well as under solvent-free conditions. No catalysts or solid supports have been used in this method. Remarkable enhancement of reaction rate has been observed in water under ultrasound-induced method. This environmentally benign procedure has provided clean formation of the products with better selectivity.
Substituted Tetrahydropyrrolopyrazine Compounds
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Page/Page column 39, (2012/03/26)
Tetrahydropyrrolopyrazine compounds, methods for their preparation, pharmaceutical compositions containing such compounds, and a method of using such compounds for the treatment of pain and other conditions mediated at least partially by Bradykinin 1 rece
SUBSTITUTED TETRAHYDROPYRROLOPYRAZINE DERIVATIVES
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Page/Page column 78, (2012/03/26)
The present invention relates to tetrahydropyrrolopyrazines, methods for the preparation thereof, medicaments containing these compounds and compounds for the use of treating, amongst other things, pain.
Microwave-induced aza-michael reaction in water: A remarkably simple procedure
Kall, Andrea,Bandyopadhyay, Debasish,Banik, Bimal K.
experimental part, p. 1730 - 1735 (2010/07/14)
Microwave-induced fast addition of several amines to conjugated carbonyl compounds has been carried out in water very efficiently in the absence of any catalyst. Copyright
Nanocrystalline copper(II) oxide catalyzed aza-Michael reaction and insertion of α-diazo compounds into N-H bonds of amines
Kantam, M. Lakshmi,Laha, Soumi,Yadav, Jagjit,Jha, Shailendra
experimental part, p. 4467 - 4469 (2009/12/01)
Nanocrystalline copper(II) oxide efficiently catalyzed the conjugate addition of aliphatic amines to α,β-unsaturated compounds to produce β-amino compounds with excellent yields under mild reaction conditions. Similarly, Glycine esters are obtained in good yields by the insertion of α-diazoacetate into N-H bonds of amines. The catalyst is used for three cycles with minimal loss of activity.
NOVEL CYCLIC HYDROCARBON COMPOUNDS FOR THE TREATMENT OF DISEASES
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Page/Page column 80-81, (2009/06/27)
The invention relates to novel cyclic hydrocarbon compounds and derivatives thereof, processes for the preparation thereof, to said compounds for use as a medicament, to said compounds for use in therapy, to pharmaceutical compositions comprising said com
Triethylammonium acetate (TEAA): A recyclable inexpensive ionic liquid promotes the chemoselective aza- and thia-Michael reactions
Verma, Akhilesh K.,Attri, Pankaj,Chopra, Varun,Tiwari, Rakesh K.,Chandra, Ramesh
experimental part, p. 1041 - 1047 (2009/11/30)
A new, highly efficient, inexpensive, recyclable, mild, convenient, and green protocol for chemoselective aza/thia-Michael addition reactions of amines/thiols to α,β-unsaturated compounds using triethylammonium acetate (TEAA) ionic liquid was developed. The catalyst can be recycled ten times and obviate the need for toxic and expensive catalysts.
