Synthesis of tetraaryl-p-benzoquinones and 2,3-diaryl-1,4-naphthoquinones via Suzuki–Miyaura cross-coupling reactions

Hassan, Zahid; Ullah, Ihsan; Ali, Iftikhar; Khera, Rasheed Ahmad; Knepper, Ingo; Ali, Asad; Patonay, Tamás; Villinger, Alexander; Langer, Peter

doi:10.1016/j.tet.2012.11.040

Cited by 20 publications

(7 citation statements)

References 84 publications

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“…22 Finally, the highly efficient Suzuki-Miyaura reaction 23 had been explored by independent research groups providing miscellaneous substituted 1,4-naphthoquinones that were studied for their physicochemical properties as organic catholytes, 24 photochromic materials, 25 and for weak intramolecular electrostatic interactions. 26 The operated reaction conditions were similar for all published procedures and represented a standard use of Pd(PPh 3 ) 4 and K 2 CO 3 , described in 2013 27 as a general method for the Suzuki reaction for DBNQ and arylboronic acids. Unfortunately, the reported conditions have a major disadvantage of requiring elevated temperatures (90-95 °C) that, together with aqueous basic media, might be fatal for either functionalized aryl fragments or diverse heterocycles.…”

Section: Syn Thesismentioning

confidence: 99%

A New Synthetic Pathway to Symmetric Bisubstituted Naphthoquinones

Migulin

2019

Synthesis

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straightforward and practical synthesis of 2,3-diiodo-1,4-naphthoquinone is reported. Based on the prepared diiodide, a new synthetic approach to symmetric bisubstituted 1,4-naphthoquinones via double Suzuki–Miyaura reaction at room temperature has been researched and developed. The presented general method combines broad-spectrum applicability, efficiency, and simplicity providing target materials in good to quantitative yields.

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Section: Syn Thesismentioning

confidence: 99%

A New Synthetic Pathway to Symmetric Bisubstituted Naphthoquinones

Migulin

2019

Synthesis

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“…We have previously reported the synthesis of 2,3diarylnaphthoquinones by double Suzuki-Miyaura reactions of 2,3-dibromonaphthoquinone. 10 Unfortunately, despite many efforts, the selective introduction of only one aryl group was not possible under a variety of conditions. Therefore, we changed the strategy by reversing the order of reactions.…”

Section: Letter Syn Lettmentioning

confidence: 99%

One-Pot Palladium-Catalyzed Synthesis of Benzo[b]carbazolediones

Hung

Ohlendorf

et al. 2015

Synlett

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dibromo-1,4-naphthoquinone 1 (0.3 mmol), the appropriate amine (0.3 mmol) and H 2 O (1 mL) were poured into a pressure tube. The reaction was set up at 60 C for 6 h, then, 2-bromophenylboronic acid (0.3 mmol), Pd (PPh 3) 4 (5 mol%), Pd 2 dba 3 (5 mol%), RuPhos (10 mol%), K 3 PO 4 (0.9 mmol) and 1,4dioxane (10 mL) were added under argon. The tube was sealed with a Teflon valve and stirred at 90 C. After 24 h, the mixture was allowed to reach room temperature, diluted with water and extracted with dichloromethane. The combined organic layers were dried over sodium sulfate and concentrated under vacuum. The crude material was purified by flash column chromatography on silica gel. Procedure B: An argon purged pressure tube was charged with 2,3-dibromo-1,4-naphthoquinone 1 (0.3 mmol) and the secondary amine (0.3 mmol), Pd (OAc) 2 (5 mol%), PPh 3 (10 mol%), tBuONa (0.9 mmol) and toluene (10 mL). The reaction was set up at 90 C for 24 h. Afterwards the mixture was allowed to reach room temperature, was diluted with water and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated under vacuum. The crude material was purified by flash column chromatography on silica gel. 5 Analytical data 2-Bromo-3-(p-tolylamino)naphthalene-1,4-dione (2b) Starting from p-toluidine with 2,3-dibromonaphthalene-1,4-dione in water at 60 C for 6 h, 2b was obtained as a dark red solid, mp = 157-158 C. 1 H NMR (300 MHz,

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“…The literature offers data that the reactions of 2,3‐dibromo‐1,4‐naphthoquinone with amines (methyl, propyl, butyl), arylamines, m, p‐aminophenols, 4‐aminopyridine, piperidine, ethylamine,, 2‐hydroxyethylamine, p‐toluidine, 2‐aminobenzothiazole, to produce 2‐Bromo‐3‐substituted‐l,4‐naphthoquinone derivatives.. It has been reported that the palladium‐catalyzed Suzuki‐Miyaura coupling reaction of 2,3‐Dibromonaphthoquinone with arylboronic acids affords the 2,3‐diarylnaphthoquinones . Also, it is known that 1,4‐naphthoquinones, possessing a substituted amino group in the 2‐position and a halogen (bromine or chloro) or a thio in the 3‐position, have shown anti‐microbial, cytotoxic, antibacterial,,, antiproliferative and antifungal activities ,,.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Electrochemistry, DFT Calculations, Antimicrobial Properties and X‐ray Crystal Structures of Some NH‐ and/or S‐ Substituted‐1,4‐quinones

et al. 2018

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The NH-, NH-,S-substituted-1,4-naphthoquinones and NH-, Ssubstituted-1,4-benzoquinones have been synthesized from the reaction between quinones (2,3-Dibromo-1,4-naphthoquinone or p-benzoquinone) and different amines. The structures of the compounds have been confirmed using FTIR, UV-Vis, 1 H-NMR, 13 C-NMR, mass MS(ESI) spectrometry and cyclic voltammetry (CV). The ground state energies of the molecules have been estimated using B3LYP functional with different basis sets based on time dependent density functional theory (TD-DFT). The theoretical ΔE gap values obtained from TD-DFT calculations have been compared with UV visible spectroscopy results. Antibacterial and antifungal activities of the synthesized compounds have been evaluated against Escherichia coli, Staphylococcus aureus and Microsporum canis, Trichophyton mentagrophytes, respectively. Two representative crystal structures of quinone derivatives, 2-(4-Fluorophenylamino)-3-bromonaphthalene-1,4-dione and 2-(3,5-Dimethylphenylthio)cyclohexa-2,5-diene-1,4-dione, are reported with CCDC 1811265 and CCDC 1811263, respectively.

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Synthesis of tetraaryl-p-benzoquinones and 2,3-diaryl-1,4-naphthoquinones via Suzuki–Miyaura cross-coupling reactions

Cited by 20 publications

References 84 publications

A New Synthetic Pathway to Symmetric Bisubstituted Naphthoquinones

A New Synthetic Pathway to Symmetric Bisubstituted Naphthoquinones

One-Pot Palladium-Catalyzed Synthesis of Benzo[b]carbazolediones

Synthesis, Electrochemistry, DFT Calculations, Antimicrobial Properties and X‐ray Crystal Structures of Some NH‐ and/or S‐ Substituted‐1,4‐quinones

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