Calix[4]resorcinols bearing γ-aminoacetal groups on the upper rim. Synthesis and properties

Vagapova, L. I.; Чачков, Д. В.; Ankushina, M. V.; Бурилов, А. Р.; Пудовик, М. А.

doi:10.1134/s107036321302014x

Russ J Gen Chem

2013

DOI: 10.1134/s107036321302014x

|View full text |Cite

Calix[4]resorcinols bearing γ-aminoacetal groups on the upper rim. Synthesis and properties

L. I. Vagapova

Д. В. Чачков

M. V. Ankushina

et al.

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2015

2017

Publication Types

Select...

Article3

Relationship

Self Cite1

Independent2

Authors

Journals

Cited by 3 publications

(2 citation statements)

References 5 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Thus obtained macromolecules are used as the supramolecular catalysts, extractants, and precursors in the synthesis of new macromolecular compounds [1,[6][7][8].In the present work we investigated the possibility of modifying calix[4]resorcinol with γ-aminobutyric acid by the Mannich reaction. γ-Aminobutyric acid and its derivatives are used as neurotransmitters in the central nervous system [9].…”

mentioning

confidence: 99%

See 1 more Smart Citation

Calix[4]resorcinols modified with γ-aminobutyric acid fragments

et al. 2015

Self Cite

View full text Add to dashboard Cite

The Mannich reaction involving amines, amino alcohols, aminoacetals, aminophosphonates, and aminophosphine oxides is one of the most convenient methods of functionalization of calix[4]resorcinols [1][2][3][4][5]. Thus obtained macromolecules are used as the supramolecular catalysts, extractants, and precursors in the synthesis of new macromolecular compounds [1,[6][7][8].In the present work we investigated the possibility of modifying calix[4]resorcinol with γ-aminobutyric acid by the Mannich reaction. γ-Aminobutyric acid and its derivatives are used as neurotransmitters in the central nervous system [9]. Recently it was shown that the complex based on 5,11,17,23-tetra-tert-butyl-25,27-bis[carboxymethoxy]-26,28-dihydroxycalix[4]arene with γ-aminobutyric acid has prolonged anticonvulsant activity [10]. Furthermore, amino acid molecules are often used as additional pharmacophore groups and are key intermediates in the synthesis of many biologically important molecules [11].Interaction of calix[4]resorcinol I with formaldehyde and γ-aminobutyric acid II in aqueous ethanol medium at a ratio of the initial reactants of 1 : 4 : 4 led to the formation of the products of incomplete substitution of the macrocycle. In the ESI mass spectrum of the precipitate obtained there were the signals of m/z 716, 831, 946, indicating the presence of mono-, di-, and trisubstituted calixarene macrocycles, respectively.We found that the optimal solution for the reaction performing was ethanol-water-DMSO mixture allowing to obtain calix[4]resorcinol comprising four amino acid III fragments at the upper rim of the molecule in a yield of 68%.The reaction of calix[4]resorcinol I with formaldehyde and γ-aminobutyric acid II in a ratio of 1 : 8 : 4 under reflux led to the formation of oxazine derivative IV in a high yield (Scheme 1).Structure and composition of the synthesized compounds III and IV were confirmed by IR, NMR 1 H and 13 C spectroscopy, mass spectrometry (ESI) and elemental analysis data. 23-dodecaene (III). A solution of 0.35 g (3.34 mmol) of amino acid II in 5 mL of water, 0.28 g (3.34 mmol) of 37% aqueous solution of formaldehyde and 20 mL of dimethyl sulfoxide were added successively to a mixture of 0.5 g (0.83 mmol) of calix[4]resorcinol I in 5 mL of ethanol. The reaction mixture was stirred at room temperature for 8 h. The solvent was distilled off in vacuum. The residue was re-precipitated from chloroform to hexane, washed with water and dried in vacuum to constant weight. Yield 0.68 g (68%), mp 177-178°C. IR spectrum, ν, cm -1 : 1610 m (С=С Ar ), 1716 m, 1733 (C=O), 2734 br (NH + ), 3422 br (OH). 1 H NMR spectrum (CDCl 3 ), δ, ppm: 0.94 t (12H, 4CH 3 CH 2 , 3 J HH 7.0 Hz), 1.99 br.s (8H, 4NCH 2 CH 2 ), 2.23-2.27 m (8H, 4CH 2 СН 3 ), 2.33 br.s (8Н,

show abstract

mentioning

confidence: 99%

“…Thus obtained macromolecules are used as the supramolecular catalysts, extractants, and precursors in the synthesis of new macromolecular compounds [1,[6][7][8].…”

mentioning

confidence: 99%

Calix[4]resorcinols modified with γ-aminobutyric acid fragments

et al. 2015

Self Cite

View full text Add to dashboard Cite

show abstract

Reactions of polyhydric phenols with nitrogen-containing acetals in the synthesis of polyphenols and heterocyclic compounds

2016

View full text Add to dashboard Cite

Reactions of nitrogen-containing acetals with aromatic nucleophiles

Газизов¹,

Бурилов²,

Pudovik³

et al. 2017

Russ. Chem. Rev.

View full text Add to dashboard Cite

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

customersupport@researchsolutions.com

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

Calix[4]resorcinols bearing γ-aminoacetal groups on the upper rim. Synthesis and properties

Cited by 3 publications

References 5 publications

Calix[4]resorcinols modified with γ-aminobutyric acid fragments

Calix[4]resorcinols modified with γ-aminobutyric acid fragments

Reactions of polyhydric phenols with nitrogen-containing acetals in the synthesis of polyphenols and heterocyclic compounds

Reactions of nitrogen-containing acetals with aromatic nucleophiles

Contact Info

Product

Resources

About