Catalytic synthesis of α-amino chromone phosphonates and their antimicrobial, toxicity and potential HIV-1 RT inhibitors based on silico screening

Jaiyeola, Abosede Oluwabukola; Anand, Krishnan; Kasumbwe, Kabange; Ramesh, Madhu; Gengan, Robert Moonsamy

doi:10.1016/j.jphotobiol.2016.11.014

Cited by 15 publications

(9 citation statements)

References 37 publications

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“…Thus, 2 0 -hydroxyacetophenones underwent Vilsmeier-Haack cyclization reaction in the presence of phosphorus(V) oxychloride (POCl 3 ) and DMF (Scheme 42) to afford an array of substituted 4-oxo-4H-chromen-3carbaldehydes. The reaction occurs usually at room temperature [300][301][302][303][304][305][306][307][308][309] but warmer conditions, at 45-80 °C, can be applied. 255,[310][311][312][313] More examples were obtained from the reaction of 2 0 -hydroxyacetophenones with oxalyl chloride in DMF at room temperature, in good yields.…”

Section: Scheme 38mentioning

confidence: 99%

Recent advances in the synthesis of 4H-chromen-4-ones (2012 − 2021)

Santos

Silva

2022

Advances in Heterocyclic Chemistry

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Section: Scheme 38mentioning

confidence: 99%

Recent advances in the synthesis of 4H-chromen-4-ones (2012 − 2021)

Santos

Silva

2022

Advances in Heterocyclic Chemistry

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“…24,25 Only a few examples have been described in the literature for the Kabachnik-Fields reaction of 3-formylchromones, primary amines and dialkyl-(DAP) or trialkyl phosphites (TAP) (Table 1). [26][27][28][29][30][31][32] In four cases, the (4-oxo-4H-chromen-3-yl)phosphonates (3−6) were synthesized in the presence of a catalyst. [26][27][28][29] In the first two examples, the condensation was performed using rhodium-boron nitride or yttria-zirconia as a catalyst in acetonitrile for long reaction time (Table 1/Entries 1 and 2).…”

Section: Introductionmentioning

confidence: 99%

“…[26][27][28][29][30][31][32] In four cases, the (4-oxo-4H-chromen-3-yl)phosphonates (3−6) were synthesized in the presence of a catalyst. [26][27][28][29] In the first two examples, the condensation was performed using rhodium-boron nitride or yttria-zirconia as a catalyst in acetonitrile for long reaction time (Table 1/Entries 1 and 2). 26,27 In a solvent-free method, using triethylamine (TEA) as a base, the desired products (5) were obtained at 60-70 °C in yields of 70-100% (Table 1/Entry 3).…”

Section: Introductionmentioning

confidence: 99%

Microwave-assisted synthesis of α-aminophosphonate-chromone hybrids using Kabachnik-Fields Reaction

Szabó¹,

Akaili²,

Tajti³

et al. 2022

Arkivoc

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An efficient, practical, and green approach for the synthesis of α-aminophosphonates incorporating a chromone moiety by the one-pot Kabachnik-Fields reaction has been developed. The three-component reactions of 3-formylchromones, primary amines and dialkyl phosphites was carried out in short reaction times in the absence of any catalyst or solvent under microwave irradiation. The method developed did not require column chromatographic separation since the products could be recovered from the reaction mixture by simple filtration. The method developed could be applied to a range of primary amines and dialkyl phosphites, which confirmed the large scope and functional-group tolerance.

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“…Substituted chromones represent one of the major classes of naturally occurring compounds . Chromones revealed variable biological activities including antimicrobial , antioxidant activity , anticancer , and neuroprotective . Chromone‐3‐carbonitriles have attracted significant consideration as highly reactive compounds, due to the presence of three electrophilic centers (C‐2, C‐4, and CN group) .…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Density Functional Theory Band Structure Calculations, Optical, and Photoelectrical Characterizations of the Novel (9‐Bromo‐3‐cyano‐5‐oxo‐1,5‐dihydro‐2H‐chromeno[4,3‐b]pyridin‐2‐ylidene)propanedinitrile

Halim

Ibrahim

2019

Journal of Heterocyclic Chem

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Ring transformation of 6‐bromochromone‐3‐carbonitrile (1) with malononitrile dimer in basic medium furnished the unexpected (9‐bromo‐3‐cyano‐5‐oxo‐1,5‐dihydro‐2H‐chromeno[4,3‐b]pyridin‐2‐ylidene)propanedinitrile (2, BCOCPP). Density functional theory, theoretical investigation of the electronic structure, geometries linear polarizability ⟨Δα⟩ (Quadrupole moment), first‐order hyperpolarizability ⟨β⟩ (Octapole moment), natural bonding orbital, molecular electrostatic potential contours, thermo‐chemical parameters, harmonic vibration frequencies, the FT‐IR spectrum of the compound (2, BCOCPP) in the solid phase was recorded, and time‐dependent density functional theory calculations at the B3LYP/6‐311G (d,p) level of theory, UV‐Vis spectra, in both ethanol and dioxane solvents have been employed for compound (2, BCOCPP). The geometrical and energetic parameters have been extensively investigated to reveal the reason behind the selective formation of compound (2, BCOCPP), instead of expected product 3. The Coulomb‐attenuating method‐B3LYP and Corrected Linear Response Polarizable Continuum Model studied for theoretically obtaining the electronic absorption spectra in gas phase, ethanol, and dioxane, respectively, and indicate a good agreement with the observed spectra. The heterojunction based on BCOCPP showed phototransient properties under various illumination intensities that give the recommendation of the studied heterojunction in the field of optoelectronic device application.

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Catalytic synthesis of α-amino chromone phosphonates and their antimicrobial, toxicity and potential HIV-1 RT inhibitors based on silico screening

Cited by 15 publications

References 37 publications

Recent advances in the synthesis of 4H-chromen-4-ones (2012 − 2021)

Recent advances in the synthesis of 4H-chromen-4-ones (2012 − 2021)

Microwave-assisted synthesis of α-aminophosphonate-chromone hybrids using Kabachnik-Fields Reaction

Synthesis, Density Functional Theory Band Structure Calculations, Optical, and Photoelectrical Characterizations of the Novel (9‐Bromo‐3‐cyano‐5‐oxo‐1,5‐dihydro‐2H‐chromeno[4,3‐b]pyridin‐2‐ylidene)propanedinitrile

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