Synthesis of some new substituted imines from aldehydes and ketones derived from quinolinic acid
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Universidade Estadual Paulista Júlio de Mesquita Filho
2023
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| author | Anwar Abdulghani Fathi |
| author_facet | Anwar Abdulghani Fathi |
| contents | Synthesis of some new substituted imines from aldehydes and ketones derived from quinolinic acid Anwar Abdulghani Fathi Yassir Shakeeb Al Jawaheri Shaimaa Samir Ismaee Química Imine Schiff base quinolinic acid benzenesulfonyl chloride In this paper, some substituted imines compounds have been prepared from quinolinic acid as a starting material. Firstly, the quinolinic acid was treated with acetic anhydride and acetic acid to form furo3,4-bpyridine-5,7-dione (1); the resulting compound was heated with urea to form 5H-pyrrolo3,4-bpyridine-5,7(6H)-dione (2). After that, it was treated with potassium hydroxide to give potassium 5,7-dioxo-5,7-dihydropyrrolo3,4-bpyridin-6-dione, which was directly and easily converted to 6-(2-(1,1'-biphenyl-4-yl)-2-oxoethyl)-5H-pyrrolo3,4-bpyridine-5,7(6H)-dione (3) by the reaction with 1-(1,1'-biphenyl-4-yl)-2-bromoethan-1-one. Finally, the resultant compound reacted with substituted aniline to give imines (4, 5). Secondly the quinolinic acid converted to 4-(5,7-dioxo-5,7-dihydro-6H-pyrrolo3,4-b pyridin-6-yl) benzenesulfonyl chloride according to our previous work, then treated with p-hydroxy acetophenone or p-hydroxy benzaldehyde to form 4-substituted bezyloxy 4-(5,7-dioxo-5,7-dihydro-6H-pyrrolo3,4-b pyridine-6-yl) benzenesulfonate (6, 7), which were finally treated with substituted aniline to form new substituted imines (8–12). 2023 artículo científico 0100-4670 https://www.redalyc.org/articulo.oa?id=42976211005 https://www.redalyc.org/journal/429/42976211005/ https://www.redalyc.org/journal/429/42976211005/html/ https://www.redalyc.org/journal/429/42976211005/42976211005.epub https://www.redalyc.org/journal/429/42976211005/movil https://doi.org/10.26850/1678-4618eqj.v48.2.2023.p49-65 en http://www.redalyc.org/revista.oa?id=429 Eclética Química application/pdf Universidade Estadual Paulista Júlio de Mesquita Filho Eclética Química (Brasil) Num.2 Vol.48 |
| format | Artículo científico |
| id | redalyc_42976211005 |
| institution | Redalyc |
| language | en |
| publishDate | 2023 |
| publisher | Universidade Estadual Paulista Júlio de Mesquita Filho |
| spellingShingle | Synthesis of some new substituted imines from aldehydes and ketones derived from quinolinic acid Anwar Abdulghani Fathi Química Imine Schiff base quinolinic acid benzenesulfonyl chloride Synthesis of some new substituted imines from aldehydes and ketones derived from quinolinic acid Anwar Abdulghani Fathi Yassir Shakeeb Al Jawaheri Shaimaa Samir Ismaee Química Imine Schiff base quinolinic acid benzenesulfonyl chloride In this paper, some substituted imines compounds have been prepared from quinolinic acid as a starting material. Firstly, the quinolinic acid was treated with acetic anhydride and acetic acid to form furo3,4-bpyridine-5,7-dione (1); the resulting compound was heated with urea to form 5H-pyrrolo3,4-bpyridine-5,7(6H)-dione (2). After that, it was treated with potassium hydroxide to give potassium 5,7-dioxo-5,7-dihydropyrrolo3,4-bpyridin-6-dione, which was directly and easily converted to 6-(2-(1,1'-biphenyl-4-yl)-2-oxoethyl)-5H-pyrrolo3,4-bpyridine-5,7(6H)-dione (3) by the reaction with 1-(1,1'-biphenyl-4-yl)-2-bromoethan-1-one. Finally, the resultant compound reacted with substituted aniline to give imines (4, 5). Secondly the quinolinic acid converted to 4-(5,7-dioxo-5,7-dihydro-6H-pyrrolo3,4-b pyridin-6-yl) benzenesulfonyl chloride according to our previous work, then treated with p-hydroxy acetophenone or p-hydroxy benzaldehyde to form 4-substituted bezyloxy 4-(5,7-dioxo-5,7-dihydro-6H-pyrrolo3,4-b pyridine-6-yl) benzenesulfonate (6, 7), which were finally treated with substituted aniline to form new substituted imines (8–12). 2023 artículo científico 0100-4670 https://www.redalyc.org/articulo.oa?id=42976211005 https://www.redalyc.org/journal/429/42976211005/ https://www.redalyc.org/journal/429/42976211005/html/ https://www.redalyc.org/journal/429/42976211005/42976211005.epub https://www.redalyc.org/journal/429/42976211005/movil https://doi.org/10.26850/1678-4618eqj.v48.2.2023.p49-65 en http://www.redalyc.org/revista.oa?id=429 Eclética Química application/pdf Universidade Estadual Paulista Júlio de Mesquita Filho Eclética Química (Brasil) Num.2 Vol.48 |
| title | Synthesis of some new substituted imines from aldehydes and ketones derived from quinolinic acid |
| topic | Química Imine Schiff base quinolinic acid benzenesulfonyl chloride |
| url | https://www.redalyc.org/articulo.oa?id=42976211005 https://www.redalyc.org/journal/429/42976211005/ https://www.redalyc.org/journal/429/42976211005/html/ https://www.redalyc.org/journal/429/42976211005/42976211005.epub https://www.redalyc.org/journal/429/42976211005/movil https://doi.org/10.26850/1678-4618eqj.v48.2.2023.p49-65 |