1,2-Naphthoquinone-4-sulfonic acid salts in organic synthesis

Ribeiro, Ruan Stevan de Almeida; Ferreira, Patrícia; Borges, Amanda de A; Forezi, Luana da S. M.; Silva, Fernando de Carvalho da; Ferreira, Vı́tor F.

doi:10.3762/bjoc.18.5

Cited by 7 publications

(7 citation statements)

References 103 publications

(108 reference statements)

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“…As shown in (Figures 8 A and B ), the results that 1:2 reagents to 2 of each drugs were formed using both of the above-mentioned methods. This indicates that a nucleophilic substitution product was formed in the weak acidic medium, as shown in the proposed mechanism [35] (Figure9).…”

Section: The Nature Of Complex and The Mechanism Of Reactionsmentioning

confidence: 66%

Spectrofluorimetric determination of adrenaline and dopamine .

Dhamra¹,

Al-Sabha²,

Al-Enizzi³

2022

JES

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A sensitive fluorometric method, with few steps and suitable for the daily routine, was made for examining adrenaline hydrochloride and dopamine hydrochloride. The reliance in this paper was on the nucleophilic substitution interaction of the mentioned drugs with 1,2-naphthoquinone sulfonate (NQS) in an aqueous pH 6 to give a fluorescent product with a maximum emission wave at ʎem 471 nm after being excited at a maximum excitation wave at ʎex 300 nm. The plots have complied within the range of 0.01-4.0, 0.01-2 µg/ml, and The detection limits (0.0062, 0.0027) and quantitation limits were (0.0207, 0.0091) µg/ml, for adrenaline and dopamine respectively. The accuracy (% recovery) was between (99.21% -100.72%) and the relative standard deviation (RSD%) is better than 0.95%. It was also found that the formed product was in a ratio of 1:2 reagent to the drug. The estimation of adrenaline and dopamine has been successfully tested on the injection, and it is in good agreement with its approved value and with that of the British Pharmacopoeia method.

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Section: The Nature Of Complex and The Mechanism Of Reactionsmentioning

confidence: 66%

Spectrofluorimetric determination of adrenaline and dopamine .

Dhamra¹,

Al-Sabha²,

Al-Enizzi³

2022

JES

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“…2-Naphthol (β-naphthol) has been in the synthesis of compounds with antimicrobial potential 40 , antitumoral 41 , antiviral 42 , and in the manufacturing of agrochemical products 43 .…”

Section: Introductionmentioning

confidence: 99%

Phytocytogenotoxicity of Esters obtained from Phenols and Phenoxyacetic Acid using the Steglich reaction

Pinheiro,

Martins,

Gonçalves

et al. 2024

Preprint

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There is a growing demand for herbicides that are more effective than conventional ones yet less harmful to ecosystems. Considering this, this study aimed to synthesize esters from phenols and phenoxyacetic acid, using compounds with known phytotoxic potential as starting materials. Phenoxyacetic acid was first synthesized and then utilized in the synthesis of seven esters through Steglich esterification, employing DCC (N,N'-dicyclohexylcarbodiimide) and DMAP (N,N-dimethylpyridin-4-amine) in the presence of phenols (thymol, vanillin, eugenol, carvacrol, guaiacol, p-cresol, and β-naphthol), yielding esters 1–7. All synthesized compounds were characterized using mass spectrometry, as well as 1H and 13C NMR. These compounds were tested for phytotoxicity to evaluate their effects on the germination and root development of sorghum (Sorghum bicolor) and lettuce (Lactuca sativa) seeds, commonly used as model plants in phytotoxicity studies and for the induction of alterations in the mitotic cycle of meristematic cells of L. sativa roots. Esters 1, 3, 4, and 5 exhibited the most significant phytotoxic activity in the initial development stages of both L. sativa and S. bicolor. These findings suggest that these compounds could serve as inspiration for the synthesis of new semi-synthetic herbicides.

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“…Redox potentials, solubility, and stability in the case of small quinones can be affected by modification with electron-donating or -withdrawing functional groups or in combination with a side chain that can form hydrogen bonds. Additionally, substituted o-quinones, besides their "classical" form, can also exist in various forms [15], like quinone methides, quinone imines, and zwitterions. This ability to adopt different structures allows modulation of their properties for different applications.…”

Section: Introductionmentioning

confidence: 99%

Studies of the Functionalized α-Hydroxy-p-Quinone Imine Derivatives Stabilized by Intramolecular Hydrogen Bond

Gaile,

Belyakov,

Dūrena

et al. 2024

Molecules

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In this work, reactions between 6,7-dichloropyrido[1,2-a]benzimidazole-8,9-diones with different benzohydrazides were studied. Nucleophilic substitution at C(6) was followed by isomerization and led to α-hydroxy-p-quinone imine derivatives. Synthesized compounds represent a combination of several structural motifs: a benzimidazole core fused with α-hydroxy-p-quinone imine, which contains a benzamide fragment. X-ray crystallography analysis revealed the formation of dimers linked through OH···O interactions and stabilization of the imine form by strong intramolecular NH···N hydrogen bonds. The protonation/deprotonation processes were investigated in a solution using UV–Vis spectroscopy and a 1H NMR titration experiment. Additionally, the electrochemical properties of 6,7-dichloropyrido[1,2-a]benzimidazole-8,9-dione and its α-hydroxy-p-quinone imine derivative as cathode materials were investigated in acidic and neutral environments using cyclic voltammetry measurements. Cathode material based on 6,7-dichloropyrido[1,2-a]benzimidazole-8,9-dione could act as a potentially effective active electrode in aqueous electrolyte batteries; however, further optimization is required.

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1,2-Naphthoquinone-4-sulfonic acid salts in organic synthesis

Cited by 7 publications

References 103 publications

Spectrofluorimetric determination of adrenaline and dopamine .

Spectrofluorimetric determination of adrenaline and dopamine .

Phytocytogenotoxicity of Esters obtained from Phenols and Phenoxyacetic Acid using the Steglich reaction

Studies of the Functionalized α-Hydroxy-p-Quinone Imine Derivatives Stabilized by Intramolecular Hydrogen Bond

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