Various Techniques for the Synthesis of 2-Nitrophenylamino-1,4-naphthoquinone Derivatives
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 nit...
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| Format: | Article |
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MDPI AG
2023-08-01
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| Series: | Reactions |
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| Online Access: | https://www.mdpi.com/2624-781X/4/3/26 |
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| author | Elisa Leyva Silvia E. Loredo-Carrillo Johana Aguilar |
| author_facet | Elisa Leyva Silvia E. Loredo-Carrillo Johana Aguilar |
| author_sort | Elisa Leyva |
| collection | DOAJ |
| description | 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 <i>ortho</i> and <i>para</i> positions, the reaction with strong acids is feasible; however, for the formation of mononitrated products, the Michael-type addition is more convenient. |
| first_indexed | 2024-03-10T22:07:30Z |
| format | Article |
| id | doaj.art-8ef4be52a5074b07b177a996ec5185bf |
| institution | Directory Open Access Journal |
| issn | 2624-781X |
| language | English |
| last_indexed | 2024-03-10T22:07:30Z |
| publishDate | 2023-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Reactions |
| spelling | doaj.art-8ef4be52a5074b07b177a996ec5185bf2023-11-19T12:44:36ZengMDPI AGReactions2624-781X2023-08-014343244710.3390/reactions4030026Various Techniques for the Synthesis of 2-Nitrophenylamino-1,4-naphthoquinone DerivativesElisa Leyva0Silvia E. Loredo-Carrillo1Johana Aguilar2Facultad de Ciencias Químicas, Universidad Autónoma de San Luis Potosí, Manuel Nava No. 6, Zona Universitaria, San Luis Potosí 78210, SLP, MexicoFacultad de Ciencias Químicas, Universidad Autónoma de San Luis Potosí, Manuel Nava No. 6, Zona Universitaria, San Luis Potosí 78210, SLP, MexicoFacultad de Ciencias Químicas, Universidad Autónoma de San Luis Potosí, Manuel Nava No. 6, Zona Universitaria, San Luis Potosí 78210, SLP, MexicoNitrated 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 <i>ortho</i> and <i>para</i> positions, the reaction with strong acids is feasible; however, for the formation of mononitrated products, the Michael-type addition is more convenient.https://www.mdpi.com/2624-781X/4/3/26nitrationnitronium ionMichael addition2-(R-phenylamino)-1,4-naphthoquinone |
| spellingShingle | Elisa Leyva Silvia E. Loredo-Carrillo Johana Aguilar Various Techniques for the Synthesis of 2-Nitrophenylamino-1,4-naphthoquinone Derivatives Reactions nitration nitronium ion Michael addition 2-(R-phenylamino)-1,4-naphthoquinone |
| title | Various Techniques for the Synthesis of 2-Nitrophenylamino-1,4-naphthoquinone Derivatives |
| title_full | Various Techniques for the Synthesis of 2-Nitrophenylamino-1,4-naphthoquinone Derivatives |
| title_fullStr | Various Techniques for the Synthesis of 2-Nitrophenylamino-1,4-naphthoquinone Derivatives |
| title_full_unstemmed | Various Techniques for the Synthesis of 2-Nitrophenylamino-1,4-naphthoquinone Derivatives |
| title_short | Various Techniques for the Synthesis of 2-Nitrophenylamino-1,4-naphthoquinone Derivatives |
| title_sort | various techniques for the synthesis of 2 nitrophenylamino 1 4 naphthoquinone derivatives |
| topic | nitration nitronium ion Michael addition 2-(R-phenylamino)-1,4-naphthoquinone |
| url | https://www.mdpi.com/2624-781X/4/3/26 |
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