β-Cyclodextrin promoted aza-Michael addition of amines to conjugated alkenes in water

Surendra, K.; Krishnaveni, N. Srilakshmi; Ramaswamy, Sridhar; Rao, K. Rama

doi:10.1016/j.tetlet.2006.01.124

Cited by 125 publications

(32 citation statements)

References 46 publications

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“…In contrast, the smooth instances of magnetic nanostructure-based catalysts that display creditable catalytic reactivity are as yet unusual in practice. We design a magnetic nanoparticles-based catalytic The aza-Michael addition reaction of acryl amides is significant for preparing kinds of β-amino carbonyl compounds from readily manufactured raw materials in a sustainable and clean method [41][42][43][44][45][46]. Recently, the researches in aza-Michael addition by the imidazolium-based polymer [47], enzymes [48][49][50][51], and room-temperature ionic liquids (RTILs) have given a novelty way to achieve the important β-amino carbonyl derivatives [28].…”

Section: Resultsmentioning

confidence: 99%

Recyclable Fe3O4 Nanoparticles Catalysts for Aza-Michael Addition of Acryl Amides by Magnetic Field

Liu

Luo

et al. 2017

Catalysts

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Abstract:A nanostructure-based catalytic system has the advantages of both homogeneous and heterogeneous catalysis. It is of great significance to develop the sustainable and green process of homogeneous catalytic reaction. We report a novel, efficient and recyclable magnetic Fe 3 O 4 nanoparticles-catalyzed aza-Michael addition reaction of acryl amides, and the magnetic nanoparticles catalysts can be recovered by external magnetic field. Both primary amine and secondary amine can react with various acryl amides providing a good output to target products successfully at room temperature. Further experiments reveal that the magnetic Fe 3 O 4 nanoparticles-based catalyst shows excellent yields, which can be recycled 10 times, and, at the same time, it maintains a high catalytically activity. In this catalytic system, the tedious separation procedures are replaced by external magnetic field, which gives us a different direction for choosing a catalyst in a nanostructure-based catalytic system.

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Section: Resultsmentioning

confidence: 99%

Recyclable Fe3O4 Nanoparticles Catalysts for Aza-Michael Addition of Acryl Amides by Magnetic Field

Liu

Luo

et al. 2017

Catalysts

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“…Products were also analyzed by GC-MS (Shimadzu MS-5000 with an Ultra-1 capillary column (above mentioned) and 1 H-NMR spectra by using a JEOL ECA-500 FT-NMR spectrometer for the identification and selectivity for the products. 13 C NMR (in CDCl 3 solvent using TMS as an internal standard) and solid 13 C MAS NMR (using a 4 mm zirconia rotor spinning at 10 kHz) were also carried out using the same spectrometer.…”

Section: Methodsmentioning

confidence: 99%

“…This reaction gives directly b-amino acid ester derivatives from a,b-carbonyl compounds. However, previous attempts have been focused on aliphatic amines because they have higher basicity than aromatic amines [6][7][8][9][10][11][12][13]. It is expected to find the catalysts with high performances even for less reactive aromatic amines, resulting in offering green chemical process.…”

Section: Introductionmentioning

confidence: 99%

Na-Y Zeolite as a Highly Active Catalyst for the Hydroamination of α,β-Unsaturated Compounds with Aromatic Amines

et al. 2008

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Hydroamination of a,b-unsaturated compounds with less reactive aromatic amines was investigated over Na-Y zeolite. Aniline gave the 99% conversion at 100°C for 5 h over Na-Y zeolite, resulting in the formation of N-[2-(methoxycarbonyl)ethyl]aniline with excellent monoselectivity. However, aromatic amines having an electronwithdrawing functional group gave moderate conversions. The reactions using recovered catalyst also occurred without significant decrease in the catalytic activity during four recycles. The regeneration of used Na-Y zeolite can be performed by the calcination. Solid-state 13 C MAS NMR measurement revealed that methyl acrylate was effectively activated by Na-Y zeolite.

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“…[31][32][33][34][35][36][37][38][39][40][41][42][43] It has been extensively used for the synthesis of β-amino carbonyl structural motifs which are embedded in a wide range of pharmaceutical intermediates, peptide analogues, antibiotics, and other biologically active molecules and drugs.…”

mentioning

confidence: 99%

Single-walled Carbon Nanotube-triethylammonium Ionic Liquid as a New Catalytic System for Michael Reaction

Attri¹,

Choi²,

Kwon³

et al. 2014

Bulletin of the Korean Chemical Society

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A new efficient catalytic method for aza/thia-Michael addition reactions of amines/thiols with higher product yields has been developed. Combining single-walled carbon nanotubes (SWCNT) with triethylammonium hydrogen phosphate (TEAP) ionic liquid (IL) can work as a catalyst. We utilized Raman spectroscopy to gain insight into the interactions between IL and SWCNT. The interactions between SWCNT with TEAP were confirmed by the increasing intensity ratios and spectral shift in wavelength of the Raman D and G bands of SWCNT. Further, the morphology of the resulting composite materials of TEAP and SWCNT was determined by using scanning electron microscopy (SEM). Higher product yield in reduced reaction time is the key advantage of using bucky gel as a catalyst for Michael reaction.

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β-Cyclodextrin promoted aza-Michael addition of amines to conjugated alkenes in water

Cited by 125 publications

References 46 publications

Recyclable Fe3O4 Nanoparticles Catalysts for Aza-Michael Addition of Acryl Amides by Magnetic Field

Recyclable Fe3O4 Nanoparticles Catalysts for Aza-Michael Addition of Acryl Amides by Magnetic Field

Na-Y Zeolite as a Highly Active Catalyst for the Hydroamination of α,β-Unsaturated Compounds with Aromatic Amines

Single-walled Carbon Nanotube-triethylammonium Ionic Liquid as a New Catalytic System for Michael Reaction

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