Mannich reaction in the calyx[4]resorcinarenes series containing organophosphorus fragments on the lower molecule rim

Knyazeva, Irina R.; Sadykova, Yu. M.; Бурилов, А. Р.; Pudovik, M. A.; Коновалов, А. И.

doi:10.1134/s1070363209110310

Cited by 7 publications

(6 citation statements)

References 1 publication

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“…The formed precipitate was filtered and dried in vacuum up to a constant weight. (9) 0.2 g (0.6 mmol) bicyclic phosphonate 3 in the mixture of 3 mL ethanol and 2 mL water was stirred until complete dissolution; after that, 0.11 g (1.2 mmol) morpholine 4b and 0.04 g (1.2 mmol) The solvent was removed, residue was reprecipitated from chloroform into diethyl ether, and the product was filtered and dried in vacuum up to a constant weight.…”

Section: Resultsmentioning

confidence: 99%

“…substrates are used as CH-acidic components in the Mannich reaction, namely ketones, ß-ketoethers, malonates, nitro compounds, and phenol derivatives [1,2]. The Mannich reaction is one of the most available methods of the synthesis of new macrocyclic structures [4,5], involving calix [4] resorcinols [6][7][8][9]. To introduce less reactive substrates to the Mannich reaction, preformed or in situ generated iminium [10] or N-acyliminium ions [11,12], as well as carbon nucleophiles, are used.…”

Section: Variousmentioning

confidence: 99%

“…Yield: 0.98 g (81%) mp >180°C (decomp. (9) 0.2 g (0.6 mmol) bicyclic phosphonate 3 in the mixture of 3 mL ethanol and 2 mL water was stirred until complete dissolution; after that, 0.11 g (1.2 mmol) morpholine 4b and 0.04 g (1.2 mmol)…”

Section: Hexaene 1-oxide (5a)mentioning

confidence: 99%

“…Many studies have been devoted to understanding of the Mannich reaction [1][2][3]. The Mannich reaction is one of the most available methods of the synthesis of new macrocyclic structures [4,5], involving calix [4] resorcinols [6][7][8][9]. The Mannich reaction is one of the most available methods of the synthesis of new macrocyclic structures [4,5], involving calix [4] resorcinols [6][7][8][9].…”

Section: Introductionmentioning

confidence: 99%

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Modification of Bicyclic Phosphonates Based on Resorcinols and Its Derivatives via the Mannich Reaction

et al. 2015

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Amino‐containing derivatives of various structures have been obtained via the Mannich reaction in a series of bicyclic phosphonates based on 2‐methylresorcinol, resorcinol, and pyrogallol with paraformaldehyde and secondary amines via the Mannich reaction. The structure and composition of the obtained compounds have been determined using 31Р and 1Н NMR spectroscopy, IR spectroscopy, mass spectrometry (MALDI‐TOF), and X‐ray analysis.

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Section: Resultsmentioning

confidence: 99%

Section: Variousmentioning

confidence: 99%

Section: Hexaene 1-oxide (5a)mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Modification of Bicyclic Phosphonates Based on Resorcinols and Its Derivatives via the Mannich Reaction

et al. 2015

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“…The mixture of solution was cooled and then evaporated to obtain a viscous solution. The viscous solution was continued with recrystallization using a mixture of 1:1 % (v/v) benzeneethanol solution until a white precipitate was obtained (Knyazeva et al 2009). The DA-host was dried in vacuum (0.2 mmHg) to obtain a constant mass and was then characterized using (IR Prestige-21 FTIR-8400s; Shimadzu Corp., Japan) and NMR (JNM GX400; JEOL, Japan).…”

Section: Methodsmentioning

confidence: 99%

Predominant hosting lead(II) in ternary mixtures of heavy metal ions by a novel of diethylaminomethyl-calix[4]resorcinarene

Yusof

Kikuchi

Kobayashi

2013

Int. J. Environ. Sci. Technol.

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Heavy metal ions from single and ternary systems of Pb(II), Cu(II), and Ni(II) adsorbed by calix [4]resorcinarenes in water-chloroform extraction were studied. Comparison was made of calix [4]resorcinarenes, 2,8,14, 20-tetraundecyl calix[4]resorcinarene-4,6,10,12,16,18,22,24-octol, and diethylaminomethyl-calix[4]resorcinarene, 5,11, 17,23-tetra(diethylaminomethyl)-2,8,14,20-tetraundecylcalix[4]resorcinarene-4,6,10,12,16,18,22,24-octol, for predominant extraction of their ions from the ternary mixture of aqueous solution at different pH in a water layer. The hosting of Pb(II) by the diethylaminomethyl-calix[4]resorcinarene occurred efficiently at pH 6-7. The hosting of Pb(II), Cu(II), and Ni(II) ions for the ternary aqueous mixture was applied to the Langmuir isotherm. Adsorption was studied using nuclear magnetic resonance spectroscopy in a water-deuterium chloroform extraction system. Results showed that as the heavy metal ions were included into the host cavity, the observation of shifted peaks of water molecules from downfield to higher field was visible in the nuclear magnetic resonance spectra, meaning that water molecules were included with heavy metal ion into the host cavity. The spectra also showed that the diethylamino group expressed formation of the coordination complex between the diethylaminomethylcalix[4]resorcinarene and Pb(II) for the purpose of predominant hosting of Pb(II).

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Synthesis of Novel Phosphorus‐Containing calix[4]resorcinols Based on Polyphenols with Phosphonium Fragment

Knyazeva

Sokolova

Шарафутдинова

et al. 2014

Heteroatom Chemistry

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The reactions of linear polyphenols containing phosphonium fragment with formaldehyde and morpholine (Mannich reaction), as well as with propionic aldehyde, have been studied. As a result, calix[4]resorcinols of novel type have been synthesized, which contain alternating methylphosphonium and ethyl substituents. The structure and composition of the products obtained were confirmed according to 1H and 31P nuclear magnetic resonance, mass spectrometry, and elemental analysis data.

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Mannich reaction in the calyx[4]resorcinarenes series containing organophosphorus fragments on the lower molecule rim

Cited by 7 publications

References 1 publication

Modification of Bicyclic Phosphonates Based on Resorcinols and Its Derivatives via the Mannich Reaction

Modification of Bicyclic Phosphonates Based on Resorcinols and Its Derivatives via the Mannich Reaction

Predominant hosting lead(II) in ternary mixtures of heavy metal ions by a novel of diethylaminomethyl-calix[4]resorcinarene

Synthesis of Novel Phosphorus‐Containing calix[4]resorcinols Based on Polyphenols with Phosphonium Fragment

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