One-Pot Synthesis of 1-Hydroxyacridones from <i>para</i>-Quinols and <i>ortho</i>-Methoxycarbonylaryl Isocyanates

Wu, Jing; Zhang, Jinzhu; Soto-Acosta, Rubén; Mao, Lili; Lian, Jiahui; Chen, Kenny; Pillon, Guy; Zhang, Guoqi; Geraghty, Robert J.; Zheng, Shengping

doi:10.1021/acs.joc.9b03307

Cited by 12 publications

(7 citation statements)

References 38 publications

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“…102–103 °C; [ 81 ]; 1 H NMR (400 MHz, CDCl 3 ) δ 7.55–7.43 (m, 2H), 7.43–7.28 (m, 3H), 6.90 (d, J = 10.1 Hz, 2H), 6.22 (d, J = 10.1 Hz, 2H), 2.71 (s, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ 185.7, 150.8, 138.7, 128.9, 128.4, 126.8, 125.2, 71.0. NMR data were in accordance with those reported in the literature [ 82 ].…”

Section: Methodssupporting

confidence: 89%

Synthesis and Antimicrobial Activity of the Pathogenic E. coli Strains of p-Quinols: Additive Effects of Copper-Catalyzed Addition of Aryl Boronic Acid to Benzoquinones

Koszelewski

Kowalczyk

Samsonowicz-Górski

et al. 2023

IJMS

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A mild and efficient protocol for the synthesis of p-quinols under aqueous conditions was developed. The pivotal role of additives in the copper-catalyzed addition of aryl boronic and heteroaryl boronic acids to benzoquinones was observed. It was found that polyvinylpyrrolidone (PVP) was the most efficient additive used for the studied reaction. The noteworthy advantages of this procedure include its broad substrate scope, high yields up to 91%, atom economy, and usage of readily available starting materials. Another benefit of this method is the reusability of the catalytic system up to four times. Further, the obtained p-quinols were characterized on the basis of their antimicrobial activities against E. coli. Antimicrobial activity was further compared with the corresponding 4-benzoquinones and 4-hydroquinones. Among tested compounds, seven derivatives showed an antimicrobial activity profile similar to that observed for commonly used antibiotics such as ciprofloxacin, bleomycin, and cloxacillin. In addition, the obtained p-quinols constitute a suitable platform for further modifications, allowing for a convenient change in their biological activity profile.

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Section: Methodssupporting

confidence: 89%

Synthesis and Antimicrobial Activity of the Pathogenic E. coli Strains of p-Quinols: Additive Effects of Copper-Catalyzed Addition of Aryl Boronic Acid to Benzoquinones

Koszelewski

Kowalczyk

Samsonowicz-Górski

et al. 2023

IJMS

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“…The one-pot synthesis of acridones 42.3 was achieved, when the reaction was performed in toluene/DBU at 130 1C for 12 h in a sealed tube. 36…”

Section: Aromatization Of P-quinolsmentioning

confidence: 99%

Site-selective and stereoselective transformations on p-quinols & p-quinamines

et al. 2023

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“…From this strategy variety of acridone derivatives were synthesized and their biological evaluation against the virus was also conducted (Scheme 29). [87] …”

Section: Reactions Of Para‐quinols and 25‐cyclo‐hexa‐dienone Monoketalmentioning

confidence: 99%

“…From this strategy variety of acridone derivatives were synthesized and their biological evaluation against the virus was also conducted (Scheme 29). [87] Arylation of silyl enol ether of quinone monoacetal was reported. Thus, compound 271 was when treated with ketene silyl acetal 272 in the presence of a hydrogen bond donor solvent such as hexafluoroisopropanol, then there was the formation of compound 273.…”

Section: Scheme 22 Reactions Of Para-quinols With Different N-contaimentioning

confidence: 99%

Molecular Complexity from Aromatics: Recent Advances in the Chemistry of paraQuinol and Masked para‐Quinone Monoketal

Chandra

Patel

2020

ChemistrySelect

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Synthesis of complex organic molecules from simple, cheap, and readily available starting materials is one of the most challenging and desirable factors in organic synthesis. In the last two decades, various methods have been developed for the de-aromatization reaction of planar aromatics compounds which lead to reactive intermediates like 2,5-cyclohexadienone ketal and para-quinol having a non-planar framework. Recently, there is an upsurge of interest in the development of the chemistry of these intermediates due to their inherent dual electrophilic and nucleophilic character. The presence of diverse functionality makes them important scaffolds and thus these are intensively utilized for the development of methodologies towards the synthesis of the highly functionalized and diverse chemical framework. These synthons have also been used in the total synthesis of many natural products. Interestingly, these are also adaptable for asymmetric synthesis. This review is a summary of the recent development of methods for 2,5-cyclohexadienone ketal and para-quinol synthesis and their application in natural product synthesis.

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One-Pot Synthesis of 1-Hydroxyacridones from para-Quinols and ortho-Methoxycarbonylaryl Isocyanates

Cited by 12 publications

References 38 publications

Synthesis and Antimicrobial Activity of the Pathogenic E. coli Strains of p-Quinols: Additive Effects of Copper-Catalyzed Addition of Aryl Boronic Acid to Benzoquinones

Synthesis and Antimicrobial Activity of the Pathogenic E. coli Strains of p-Quinols: Additive Effects of Copper-Catalyzed Addition of Aryl Boronic Acid to Benzoquinones

Site-selective and stereoselective transformations on p-quinols & p-quinamines

Molecular Complexity from Aromatics: Recent Advances in the Chemistry of paraQuinol and Masked para‐Quinone Monoketal

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