Catalytic, ultrasonic, and microwave-assisted synthesis of naphthoquinone derivatives by intermolecular and intramolecular N-arylation reactions

Leyva, Elisa; Loredo‐Carrillo, Silvia E.; López, Lluvia I.

doi:10.1016/b978-0-12-819848-3.00004-9

Cited by 3 publications

(7 citation statements)

References 82 publications

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“…The reaction was also carried out under microwave conditions. The results are shown in Tables 5 and 6 [56,57]. ---------3a 2 6.1 65.5 61.0 3a 3 ---70.7 51.6 3a 4 ---22.0 23.0 ------3a 1 23.3 28.7 2a 2 18.1 10.8 1a ------3a2…”

Section: Naphthoquinonementioning

confidence: 97%

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Various Techniques for the Synthesis of 2-Nitrophenylamino-1,4-naphthoquinone Derivatives

Leyva,

Loredo-Carrillo,

Aguilar

2023

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Nitrated products are important since they are intermediates in the synthesis of other compounds, such as explosives, perfumes, dyes and plastics, among others, and they have an easy capacity to convert into other functional groups. The synthesis of compounds with biological activity that have a nitro group in their structure is relevant to improving and/or enhancing their effect. In this work, different methodologies for the nitration of naphthoquinone derivative compounds are presented. The nitration of 3-R-2-(phenylamino)-1,4-naphthoquinone derivatives was carried out with nitric acid and sulfuric acid; milder reaction conditions were also established by diluting the acids or performing the reaction with weaker acids. Other methodologies were tested using nitrate salts for mononitrate product synthesis. We used a solvent-free reaction with oxalic acid using 3-R-2-(phenylamino)-1,4-naphthoquinones (R=H, Br or Cl), noting that the electronegativity of the chlorine group is decisive for achieving nitration with good yields. Finally, a Michael addition was performed with some nitrated anilines. To obtain denitrated compounds in the ortho and para positions, the reaction with strong acids is feasible; however, for the formation of mononitrated products, the Michael-type addition is more convenient.

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Section: Naphthoquinonementioning

confidence: 97%

“…For this methodology, the same catalysts as under ambient conditions were used. The synthesis of the 2NO 2 PAN and 2F-4NO 2 molecules was not possible under microwave radiation [57].…”

Section: Naphthoquinonementioning

confidence: 99%

Various Techniques for the Synthesis of 2-Nitrophenylamino-1,4-naphthoquinone Derivatives

Leyva,

Loredo-Carrillo,

Aguilar

2023

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“…With a Lewis acid catalyst with strong oxidation properties such as CeCl3 (b), the reaction takes place in four hours, and high yields of products are obtained (60-90%). Performing the reaction under an alternative source of energy (c), e.g., microwave (MW) and ultrasound (US), results in higher yields (70-95%) of cleaner compounds within minutes (15-50 min) of reaction (Figure 3) [10,[37][38][39][40]. Leyva et al, 2017, synthesized anilino (PAN: phenylamino naphthoquinone) and dianilino derivatives.…”

Section: Chemical Modification Of Nqs Structures With Nitrogen Groupsmentioning

confidence: 99%

“…Since many quinones have a planar structure, they can function as DNA-intercalating agents [7,10,11,71].…”

Section: Pharmaceutical Relevance and Evidence On The Antitumoral And...mentioning

confidence: 99%

“…They constitute a large group of natural and synthetic compounds with important physicochemical and biological properties. Thus, quinones have been applied in several areas, for instance: (1) to develop novel synthetic and heterocyclic derivatives, (2) to be used as molecular probes to study biological interactions, and (3) to synthesize therapeutic agents [7][8][9][10][11][12][13].…”

Section: Introductionmentioning

confidence: 99%

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The Relevance and Insights on 1,4-Naphthoquinones as Antimicrobial and Antitumoral Molecules: A Systematic Review

et al. 2023

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Natural product derivatives are essential in searching for compounds with important chemical, biological, and medical applications. Naphthoquinones are secondary metabolites found in plants and are used in traditional medicine to treat diverse human diseases. Considering this, the synthesis of naphthoquinone derivatives has been explored to contain compounds with potential biological activity. It has been reported that the chemical modification of naphthoquinones improves their pharmacological properties by introducing amines, amino acids, furan, pyran, pyrazole, triazole, indole, among other chemical groups. In this systematic review, we summarized the preparation of nitrogen naphthoquinones derivatives and discussed their biological effect associated with redox properties and other mechanisms. Preclinical evaluation of antibacterial and/or antitumoral naphthoquinones derivatives is included because cancer is a worldwide health problem, and there is a lack of effective drugs against multidrug-resistant bacteria. The information presented herein indicates that naphthoquinone derivatives could be considered for further studies to provide drugs efficient in treating cancer and multidrug-resistant bacteria.

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A review on the synthesis and application of naphthoquinone-based drugs

Khan,

Rani,

Aslam

et al. 2023

Results in Chemistry

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Catalytic, ultrasonic, and microwave-assisted synthesis of naphthoquinone derivatives by intermolecular and intramolecular N-arylation reactions

Cited by 3 publications

References 82 publications

Various Techniques for the Synthesis of 2-Nitrophenylamino-1,4-naphthoquinone Derivatives

Various Techniques for the Synthesis of 2-Nitrophenylamino-1,4-naphthoquinone Derivatives

The Relevance and Insights on 1,4-Naphthoquinones as Antimicrobial and Antitumoral Molecules: A Systematic Review

A review on the synthesis and application of naphthoquinone-based drugs

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