A novel, simple and effective synthesis of the hydroxybenzyl derivative of resorcinarene and the modification possibilities thereof

Iwanek, Waldemar; Stefańska, Karolina

doi:10.1016/j.tetlet.2015.02.026

Cited by 6 publications

(5 citation statements)

References 49 publications

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“…In general, the values of the calculated activation energies for the formation of o-QMR [4]A from ABR [4]A are very close and are about 30 kcal mol −1 . This is consistent with experimental observations showing that any of these derivatives can be used to generate o-QMR [4]A, especially methoxy and ethoxybenzyl derivatives of resorcin [4]arene, but also HBR [4]A [40].…”

Section: Generation Of O-qmr[4]a From Hbr[4]a and Abr[4]a And Reactio...supporting

confidence: 91%

Theoretical calculations of formation and reactivity of o -quinomethide derivatives of resorcin[4]arene with reference to empirical data

Iwanek

2022

R. Soc. open sci.

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This paper describes theoretical reaction pathways of alkoxybenzyl derivatives of resorcin[4]arene leading to the formation of o -quinomethide derivatives of resorcin[4]arene ( o- QMR[4]A). For each case, the activation energies for the formation of one o -QMR[4]A unit and the activation energies for the backward reaction were calculated. Based on the calculated reaction pathways, the reaction mechanism of o -QMR[4]A formation was proposed. Using the example of o -QMR[4]A generated from a methoxy derivative of resorcin[4]arene, the activation energies with selected nucleophiles were calculated and the reaction mechanisms discussed. Reaction path calculations were performed using the nudged elastic band method and semiempirical extended tight-binding method (GFN2-xTB). Using hydroxybenzyl derivatives of resorcin[4]arene as an example, a comparison of calculated activation energies by selected density-functional theory methods with GFN2-xTB and B97-3c geometries was performed. B97-3c and wB97XD methods were used to calculate the energies of the reactants (R), transition states (TS) and products (P) of the analysed reactions. Theoretical reaction mechanisms were discussed with respect to the orbital-weighted Fukui dual descriptor (Δ f w ) and experimental data.

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Section: Generation Of O-qmr[4]a From Hbr[4]a and Abr[4]a And Reactio...supporting

confidence: 91%

Theoretical calculations of formation and reactivity of o -quinomethide derivatives of resorcin[4]arene with reference to empirical data

Iwanek

2022

R. Soc. open sci.

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“…Iwanek and coworkers reported another variation of the Mannich type reaction. [74][75][76][77] The method was able to quantitatively form hydroxybenzyl resorcin [4]arene derivatives in onepot. The approach holds value as it shortens the route to accessing such derivatives, from three steps in resorcin [4]arene ethers and four steps in cavitands to just two.…”

Section: Electrophilic Aromatic Substitutionmentioning

confidence: 99%

“…al. performed lithium-halogen exchange on cavitands, [74,98] compounds that are based on the resorcin [4]arene scaffold, to achieve selective derivatization of these molecules (Scheme 7). Starting with the bridging of the tetrabromoresorcin [4]arene 2 to form the tetrabrominated cavitand 17, reactions of 17 with equivalents of n-butyllithium, quenching with electrophiles, managed to furnish functionalized cavitands.…”

Section: Lithium-halogen Exchangementioning

confidence: 99%

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Methodologies for the Derivatization of Resorcin[4]arenes at the Upper Rim ortho‐Positions

et al. 2022

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Resorcin[4]arenes are not as extensively studied as their sister compounds, calix[4]arenes, owing to challenges in synthetic methodologies for their derivatization from the perceptive of molecular economy. In this tutorial review, we briefly illustrate the summary of their access methodologies together with their limitations, focusing at the derivatization of the ortho‐positions in the upper rim. We hope to spark a refreshed surge in the development of these derivatization strategies, allowing access to novel molecules and futuristic applications, putting resorcin[4]arenes at the center stage of research for which they were meant.

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“…These will provide cyclic structure of the molecule and even arrangement of two hydroxyl groups. 21 Several artificial receptors were developed for the detection of protein surface. 22 Disorder of the biotic substances have create very serious difficulties in the human body.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of supramolecular receptors for amino acid recognition

Upadhyay¹,

Parekh²

2019

10.5267/j.ccl

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The derivatives of 2,6-dihydroxyacetophenone [4]arene were synthesized via one-step in the presence of base catalyzed cyclocondensation reaction of equimolar volumes of different aliphatic aldehydes and 2,6-dihydroxyacetophenone. All the compounds were purified by column chromatography and characterized by 1 H-NMR Spectroscopy, 13 C-NMR Spectroscopy, IR Spectroscopy, and Mass spectrometry techniques. The compounds were provided with good yield and can be successfully useful for various amino acid detection because of the four ketone groups in 2,6-Dihydroxyaceto-phenone[4]arene were able to react with the amino group of amino acid to give a stable product formation. It was caused by the intermolecular hydrogen bonded between the two groups, ketone and carboxylic group of amino acid. This recognition of amino acid was carried out in UV-vis spectroscopic technique.

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A novel, simple and effective synthesis of the hydroxybenzyl derivative of resorcinarene and the modification possibilities thereof

Cited by 6 publications

References 49 publications

Theoretical calculations of formation and reactivity of o -quinomethide derivatives of resorcin[4]arene with reference to empirical data

Theoretical calculations of formation and reactivity of o -quinomethide derivatives of resorcin[4]arene with reference to empirical data

Methodologies for the Derivatization of Resorcin[4]arenes at the Upper Rim ortho‐Positions

Synthesis of supramolecular receptors for amino acid recognition

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