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Grebenyuk, A. D.; Andreev, S. A.; Stempnevskaya, I. A.; Левкович, М. Г.; Ташмухамедова, А. К.

doi:10.1023/a:1017530731688

Cited by 8 publications

(3 citation statements)

References 4 publications

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“…4′-Nitro and 4′,4″-and 4′,5″-dinitro-DB18C6 were prepared as before [10]; 4′-amino-DB18C6, according to the literature [11] by reduction of 4′-nitro-DB18C6 with hydrazine hydrate over Raney nickel in dioxane. Yield 74%, mp 142-144°C.…”

Section: Methodsmentioning

confidence: 99%

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Dibenzo-18-crown-6 modified with kojic acid fragments

2006

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In continuation of our research on the modification of dibenzo-18-crown-6 (DB18C6) with natural compounds [1-5], we synthesized several new heterocyclic derivatives by coupling kojic acid (5-hydroxy-2-hydroxymethyl-γ-pyrone) with 4′-(DB18C6-yl)-diazonium chloride and 4′,4″-and 4′,5″-di-(DB18C6-yl)-diazonium dichlorides.Kojic acid is a natural heterocyclic compound produced by many species of the genus Aspergilus, certain species of Penicillum, and certain acetic-acid bacteria [6].The prepared derivatives were potential double ionophores, i.e., capable of binding cations of alkaline and alkalineearth elements (through the macrocyclic portion) [7] and cations of d-transition metals (through the kojic acid portion) [8,9].The synthons for preparing the products were 4′-nitro-and 4′,4″-and 4′,5″-dinitro-DB18C6 [10], which were reduced to 4′-amino-(1) and 4′,4″-and 4′,5″-diamino-DB18C6 (2 and 3) according to the literature [11].Kojic acid is known to undergo electrophilic substitution (halogenation, alkylation, azo-coupling) at the 6-position [12]. The diazonium salts were prepared from amines 1-3 and underwent azo-coupling with kojic acid according to the scheme as before [13].The structures of the products were determined by PMR and IR spectra. The PMR spectra of 4, 5, and 6 gave multiplets for the aromatic protons of DB18C6 and the aromatic proton in the 3-position of kojic acid at 6.98-6.66 ppm (4) and 6.95-6.75 ppm (5 and 6). The macrocycle protons appeared as two multiplets at 4.10-3.90 ppm (α-OCH 2 ) and 3.90-3.62 ppm (β-OCH 2 ) (4) and at 4.20-4.02 ppm (α-OCH 2 ) and 3.95-3.80 ppm (β-OCH 2 ) (5 and 6). The kojic-acid methylene protons appeared as a singlet at 3.40 ppm (4) and 3.45 ppm (5 and 6); the OH proton, at 1.24 ppm (4) and 1.15 ppm (5 and 6).

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Section: Methodsmentioning

confidence: 99%

“…The synthons for preparing the products were 4′-nitro-and 4′,4″-and 4′,5″-dinitro-DB18C6 [10], which were reduced to 4′-amino-(1) and 4′,4″-and 4′,5″-diamino-DB18C6 (2 and 3) according to the literature [11].…”

Section: -6mentioning

confidence: 99%

Dibenzo-18-crown-6 modified with kojic acid fragments

2006

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“…and metal nitrates and sulfates in polyphosphoric acid it was found that the substituent entering one of the benzene rings affects the distribution of electron density in the second ring [1][2][3]. This effect was confirmed by nonidentical splitting of the signals for the carbon atoms of the ring in the 13 C NMR spectra [1,4].…”

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Acylation of Dibenzo-18-crown-6 with Alkali-metal Acetates in Polyphosphoric Acid

Saifullina

Ташмухамедова

2005

Chem Heterocycl Compd

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Synthesis of some novel quinone diimine derivatives of benzo‐15‐crown‐5 for application in Hg²⁺ recognition

et al. 2013

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A series of novel fluoroionophore bearing derivatives of benzo-15-crown-5 were synthesized by the amination of benzo-15-crown-5 followed by condensation with different quinones in the presence of titanium tetrachloride (TiCl4 ) and 1,4-diazabicyclo-[2.2.2]octane. The compounds were characterized by infrared, (1) H and (13) C nuclear magnetic resonance, mass spectroscopy and elemental analysis. Absorption and fluorescence spectral characteristics of these compounds were studied. It was observed that the anthraquinone derivative was acting as an Hg(2+) ion sensor.

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Cited by 8 publications

References 4 publications

Dibenzo-18-crown-6 modified with kojic acid fragments

Dibenzo-18-crown-6 modified with kojic acid fragments

Acylation of Dibenzo-18-crown-6 with Alkali-metal Acetates in Polyphosphoric Acid

Synthesis of some novel quinone diimine derivatives of benzo‐15‐crown‐5 for application in Hg²⁺ recognition

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Untitled

Cited by 8 publications

References 4 publications

Dibenzo-18-crown-6 modified with kojic acid fragments

Dibenzo-18-crown-6 modified with kojic acid fragments

Acylation of Dibenzo-18-crown-6 with Alkali-metal Acetates in Polyphosphoric Acid

Synthesis of some novel quinone diimine derivatives of benzo‐15‐crown‐5 for application in Hg2+ recognition

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Synthesis of some novel quinone diimine derivatives of benzo‐15‐crown‐5 for application in Hg²⁺ recognition