Synthesis and structure of new 3-pyrazolinylcoumarins and 3-pyrazolinyl-2-quinolones

Traven, V. F.; Manaev, A. V.; Voevodina, I. V.; Okhrimenko, I. N.

doi:10.1007/s11172-008-0195-4

Cited by 14 publications

(6 citation statements)

References 12 publications

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“…This situation is further complicated by the fact that full NMR assignments are often not performed due to a partial or complete overlap of the proton signals of the coumarinic moiety and also of the aryl side group. The same situation is found in the literature regarding the assignment of the 13 C NMR spectral data for many coumarin derivatives 18–23…”

Section: Introductionsupporting

confidence: 75%

Complete assignment of the ¹H and ¹³C NMR spectra of antimicrobial 4‐arylamino‐ 3‐nitrocoumarin derivatives

Dekić¹,

Radulović²,

Vukićević³

et al. 2010

Magnetic Reson in Chemistry

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Herein, we describe the synthesis and complete assignment of the (1)H and (13)C NMR chemical shifts of a series of antimicrobial 4-arylamino-3-nitrocoumarin derivatives based on a combination of (1)H and (13)C NMR, (1)H-(1)H-COSY, NOESY, HSQC and HMBC experiments. Conformational effects upon the chemical shifts of the coumarin moiety arising from the anisotropy of the aryl side group are briefly discussed. This study provides the first complete and fully assigned NMR data for this important group of antimicrobial compounds and bridges the gap existing in the literature with regard to NMR structural data for 4-arylamino-3-nitrocoumarins.

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Section: Introductionsupporting

confidence: 75%

Complete assignment of the ¹H and ¹³C NMR spectra of antimicrobial 4‐arylamino‐ 3‐nitrocoumarin derivatives

Dekić¹,

Radulović²,

Vukićević³

et al. 2010

Magnetic Reson in Chemistry

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“…Compounds L2 and L3, boron difluoride complex 3-acetyl-4-hydroxycoumarin have been completely characterized by NMR, IR, elemental analysis and mass spectrometry in [ 14 , 15 , 16 ]. The synthetic methodology has followed the same steps and sequential reactions.…”

Section: Methodsmentioning

confidence: 99%

Exploring Coumarin-Based Boron Emissive Complexes as Temperature Thermometers in Polymer-Supported Materials

Pedro

Duarte

Cheptsov

et al. 2023

Sensors

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Three coumarin-based boron complexes (L1, L2 and L3) were designed and successfully incorporated into polymeric matrixes for evaluation as temperature probes. The photophysical properties of the complexes were carried out in different solvents and in the solid state. In solution, compound L1 exhibited the highest fluorescence quantum yield, 33%, with a positive solvatochromism also being observed on the absorption and emission when the polarity of the solvent increased. Additionally in the presence of anions, L1 showed a colour change from yellow to pink, followed by a quenching in the emission intensity, which is due to deprotonation with the formation of a quinone base. Absorption and fluorescence spectra of L1 were calculated at different temperatures by the DFT/B3LYP method. The decrease in fluorescence of compound L1 with an increase in temperature seems to be due to the presence of pronounced torsional vibrations of the donor and acceptor fragments relative to the single bond with C(carbonyl)-C (styrene fragment). L1, L2 and L3, through their incorporation into the polymeric matrixes, became highly emissive by aggregation. These dye@doped polymers were evaluated as temperature sensors, showing an excellent fluorescent response and reversibility after 15 cycles of heating and cooling.

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“…The intermediate chalcone compounds 4a-d were prepared by conventional Claisen-Schmidt condensation reaction of 1 with the previously mentioned aryl aldehydes in the presence of piperidine drops in ethanol [41][42][43] (Scheme 2). The coumarin-pyrazoline hybrids 5-7 were synthesized through 1,4-addition of hydrazine hydrate or phenyl hydrazine to the α,ß unsaturated carbonyl moiety of the chalcones 4a-d, followed by dehydration and rearrangement (Scheme 2).…”

Section: Methodsmentioning

confidence: 99%

“…The chalcone compounds 4a, 4b, 4c and 4d were prepared according to the reported methods [41][42][43].…”

Section: A-dmentioning

confidence: 99%

3-Substituted-4-hydroxycoumarin as a new scaffold with potent CDK inhibition and promising anticancer effect: Synthesis, molecular modeling and QSAR studies

Latif

Batran

Khedr

et al. 2016

Bioorganic Chemistry

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Synthesis and structure of new 3-pyrazolinylcoumarins and 3-pyrazolinyl-2-quinolones

Cited by 14 publications

References 12 publications

Complete assignment of the ¹H and ¹³C NMR spectra of antimicrobial 4‐arylamino‐ 3‐nitrocoumarin derivatives

Complete assignment of the ¹H and ¹³C NMR spectra of antimicrobial 4‐arylamino‐ 3‐nitrocoumarin derivatives

Exploring Coumarin-Based Boron Emissive Complexes as Temperature Thermometers in Polymer-Supported Materials

3-Substituted-4-hydroxycoumarin as a new scaffold with potent CDK inhibition and promising anticancer effect: Synthesis, molecular modeling and QSAR studies

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Synthesis and structure of new 3-pyrazolinylcoumarins and 3-pyrazolinyl-2-quinolones

Cited by 14 publications

References 12 publications

Complete assignment of the 1H and 13C NMR spectra of antimicrobial 4‐arylamino‐ 3‐nitrocoumarin derivatives

Complete assignment of the 1H and 13C NMR spectra of antimicrobial 4‐arylamino‐ 3‐nitrocoumarin derivatives

Exploring Coumarin-Based Boron Emissive Complexes as Temperature Thermometers in Polymer-Supported Materials

3-Substituted-4-hydroxycoumarin as a new scaffold with potent CDK inhibition and promising anticancer effect: Synthesis, molecular modeling and QSAR studies

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Complete assignment of the ¹H and ¹³C NMR spectra of antimicrobial 4‐arylamino‐ 3‐nitrocoumarin derivatives

Complete assignment of the ¹H and ¹³C NMR spectra of antimicrobial 4‐arylamino‐ 3‐nitrocoumarin derivatives