Nitroaldol-reaction of aldehydes in the presence of non-activated Mg:Al 2:1 hydrotalcite; a possible new mechanism for the formation of 2-aryl-1,3-dinitropropanes

Cwik, Agnieszka; Fuchs, Alexandra; Hell, Zoltán; Clacens, Jean‐Marc

doi:10.1016/j.tet.2005.02.055

Cited by 56 publications

(25 citation statements)

References 35 publications

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“…All samples were degassed to a pressure below 3 mm Hg at 423 K prior to analysis. 13 C-CP/MAS NMR spectra were recorded at 100.62 MHz on a Bruker ACP-400 spectrometer. Samples were spun at the magic angle at 3.5 kHz on a zirconia rotor.…”

Section: Characterization Of the Catalystmentioning

confidence: 99%

“…The silica-supported ethanolamine phase was examined by using various instrumental techniques. 13 C-CP/MAS NMR revealed the presence of ethanolamine on the catalyst surface. Figure 2a shows the spectrum for the catalyst, which exhibits the two typical signals for the two methylene groups in ethanolamine.…”

Section: Characterization Of the Catalystmentioning

confidence: 99%

“…The greatest advantages of using a heterogeneous catalyst in this context are the ease with which it can be removed from the reaction medium and the ability to reuse it over several reaction cycles. Heterogeneous catalysts consisting of alumina [8][9][10], anionic clays [11][12][13][14] and metal oxides [7][8][9][10][11][12][13][14][15], among other substances, have so far provided excellent activity and conversion results in many applications.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of (E)-nitroalkenes Catalysed by Ethanolamine Supported on Silica

et al. 2009

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A simple method for preparing (E)-nitroalkenes based on a Henry reaction in the presence of a heterogenized homogeneous catalyst consisting of silica-supported ethanolamine is proposed. With 4-substituted benzaldehydes, the reaction gives the corresponding (E)-nitrostyrenes in high yields and a short time. Heterocyclic carboxaldehydes also give good results, but the presence of an N or S atom in the ring has a slightly adverse effect on the reaction. The synthetic process is quite novel and interesting. The catalyst remains active and exhibits no substantial loss of activity or selectivity over up to three reaction cycles.

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Section: Characterization Of the Catalystmentioning

confidence: 99%

Section: Characterization Of the Catalystmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis of (E)-nitroalkenes Catalysed by Ethanolamine Supported on Silica

et al. 2009

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“…Nitroaldol condensation is also a key reaction in the synthesis of b-nitroalkanols which are extensively important intermediates in variant organic transformations [21,22]. b-nitroalkanols can further be converted to obtain 2-aminoalcohols for intermediates in chloroamphenicol, [23] ephedrine, norephedrine [24,25], drugs like S-propanolol [26,27] and to achieve amino sugars and ketones [28].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Silica–Polymer Nanocomposites Functionalized with Piperazine for the Synthesis of β-Nitro Alcohols

Sachdev

Dubey

2011

Catal Lett

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In order to compare the activity and selectivity for the synthesis of b-nitro alcohols, piperazine was functionalized directly and after surface modification into the ordered mesoporous SBA-15 framework. The materials were characterized by powder X-ray diffraction, N 2 -adsorption-desorption isotherm, FT-IR, SS-NMR and scanning electron microscopy. The catalyst synthesized via surface modification under solvent free conditions showed very high activity and selectivity of b-nitro alcohols compared to the one synthesized by direct functionalization of SBA-15. Finally the possible reaction pathways were explained mechanistically.

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“…All products are reported in literature. 17,18,19,20 2-Nitro-1-phenylethanol (entry 1) 12, 134.86, 130.24, 129.78, 126.13, 70.20 12, 134.86, 130.24, 129.78, 129.32, 126.13, 124.04, 70.20 (m, 9H), 5.43-5.40 (m, 1H), 4.59-4.48 (m, 2H), 2.49 (bs, 1H). 13 C NMR (CDCl3,50 MHz): 157.86,140.45,130.29,129.83,123.71,12.36,119.11,118.73,115.97,70.50 (m, 1H), 7.91-7.88 (m, 1H), 7.85-7.84 (m, 1H), 7.73-7.71 (m, 1H), 7.26-7.30 (m, 3H), 6.27-6.24 (m, 1H), 4.68-4.65 (m, 2H), 2.89 (bs, 1H).…”

mentioning

confidence: 99%

TMEDA Catalyzed Henry (Nitroaldol) Reaction under Metal and Solvent-free Conditions

2009

Bulletin of the Korean Chemical Society

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The Henry (nitroaldol) reaction proceeds under mild conditions with catalytic amount of tetramethylethylenediamine (TMEDA) to afford β-nitro alkanol in considerably excellent yield. Structurally diverse aldehydes react with nitromethane in presence of 0.3 equiv of TMEDA under solvent-free condition at rt. The low catalytic loading and mild reaction condition are the key features of the catalytic method.

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Nitroaldol-reaction of aldehydes in the presence of non-activated Mg:Al 2:1 hydrotalcite; a possible new mechanism for the formation of 2-aryl-1,3-dinitropropanes

Cited by 56 publications

References 35 publications

Synthesis of (E)-nitroalkenes Catalysed by Ethanolamine Supported on Silica

Synthesis of (E)-nitroalkenes Catalysed by Ethanolamine Supported on Silica

Synthesis and Characterization of Silica–Polymer Nanocomposites Functionalized with Piperazine for the Synthesis of β-Nitro Alcohols

TMEDA Catalyzed Henry (Nitroaldol) Reaction under Metal and Solvent-free Conditions

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