Synthesis of some new substituted imines from aldehydes and ketones derived from quinolinic acid
| Autor: | Anwar Abdulghani Fathi, Yassir Shakeeb Al Jawaheri, Shaimaa Samir Ismaee |
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| Jazyk: | angličtina |
| Rok vydání: | 2023 |
| Předmět: | |
| Zdroj: | Eclética Química, Vol 48, Iss 2, Pp 49-65 (2023) |
| Druh dokumentu: | article |
| ISSN: | 0100-4670 1678-4618 |
| DOI: | 10.26850/1678-4618eqj.v48.2.2023.p49-65 |
| Popis: | 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 furo[3,4-b]pyridine-5,7-dione (1); the resulting compound was heated with urea to form 5H-pyrrolo[3,4-b]pyridine-5,7(6H)-dione (2). After that, it was treated with potassium hydroxide to give potassium 5,7-dioxo-5,7-dihydropyrrolo[3,4-b]pyridin-6-dione, which was directly and easily converted to 6-(2-([1,1'-biphenyl]-4-yl)-2-oxoethyl)-5H-pyrrolo[3,4-b]pyridine-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-pyrrolo[3,4-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-pyrrolo[3,4-b] pyridine-6-yl) benzenesulfonate (6, 7), which were finally treated with substituted aniline to form new substituted imines (8–12). |
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