Direct Nitration of 3‐Arylamino‐2‐chloro‐1,4‐naphthoquinones.

Win, Thida; Yerushalmi, Sarit; Bittner, Shmuel

doi:10.1002/chin.200546092

Cited by 2 publications

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“…It is also possible to make a second substitution at position 3 of the naphthoquinone ring since, with the first reaction, the electrophilicity of said position is decreased due to the electronic effects of the substituents. By introducing a highly electroattracting group, position 3 recovers its electrophilicity [45][46][47].…”

Section: Resultsmentioning

confidence: 99%

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: Resultsmentioning

confidence: 99%

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

Leyva,

Loredo-Carrillo,

Aguilar

2023

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“…However, they can be obtained by an alternative two-step synthesis was developed. In the first step, 2-anilino-3-chloro-1,4-naphthoquinones were prepared by the classical Michael type addition-elimination reaction [ 33 , 36 ]. The phenyl group was then nitrated via direct electrophilic aromatic substitution in the second step.…”

Section: Discussionmentioning

confidence: 99%

“…Interestingly, 2-arylamino-1,4-naphthoquinones 28a – d treated with nitrosylsulfuric acid in acetic acid are converted to benzo[ b ]phenazine-6,11-dione oxides 29a – d . Usually the 2-arylamino-3-chloro-1,4-naphthoquinones in reaction with HNO 3 /H 2 SO 4 are nitrated on the arylamino group [ 36 ]. Thus, the reaction of aminoquinones 28a – d with nitrosylsulfuric acid takes another pathway than that described in the literature.…”

Section: Discussionmentioning

confidence: 99%

A Survey of Synthetic Routes and Antitumor Activities for Benzo[g]quinoxaline-5,10-diones

et al. 2020

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Anthracycline antibiotics play an important role in cancer chemotherapy. The need to improve their therapeutic index has stimulated an ongoing search for anthracycline analogs with enhanced properties. This review aims to summarize the common synthetic approaches to benzo[g]quinoxaline-5,10-diones and their uses in heterocyclic chemistry. Because of the valuable biological activities of the 1,4-diazaanthraquinone compounds, a summary of the most promising heterocyclic quinones is provided together with their antitumor properties.

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Direct Nitration of 3‐Arylamino‐2‐chloro‐1,4‐naphthoquinones.

Cited by 2 publications

References 0 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

A Survey of Synthetic Routes and Antitumor Activities for Benzo[g]quinoxaline-5,10-diones

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