Ejjoummany Abdelaziz, Elie Jonathan, El Hakmaoui Ahmed, Akssira Mohamed, Routier Sylvain, Buron Frédéric
Institut de Chimie Organique et Analytique, Université d'Orléans, UMR CNRS 7311, BP 6759, CEDEX 2, F-45067 Orléans, France.
Faculté des Sciences et Technique, Université Hassan II-Casablanca, BP 146, Mohammedia 28800, Morocco.
Molecules. 2023 Aug 1;28(15):5811. doi: 10.3390/molecules28155811.
The first access to polyfunctionnalized pyrrolo[3,4-]pyrazole-4,6-(2,5)-dione derivatives is reported. The series were generated from diethyl acetylenedicarboxylate and arylhydrazines, which afforded the key intermediates bearing two functional positions. The annellation to generate the maleimide moiety of the bicycle was studied. Moreover, an efficient palladium-catalyzed C-C and C-N bond formation via Suzuki-Miyaura or Buchwald-Hartwig coupling reactions in C-6 position was investigated from 6-chloropyrrolo[3,4-]pyrazole-4,6-(2,5)-diones. This method provides novel access to various 1,6 di-substituted pyrrolo[3,4-] pyrazole-4,6-(2,5)-diones.
首次报道了多官能化吡咯并[3,4 - ]吡唑 - 4,6 - (2,5) - 二酮衍生物的合成方法。该系列化合物由乙炔二羧酸二乙酯和芳基肼反应生成，得到带有两个官能团位置的关键中间体。对生成双环马来酰亚胺部分的环化反应进行了研究。此外，还研究了通过铃木 - 宫浦或布赫瓦尔德 - 哈特维希偶联反应在6 - 氯吡咯并[3,4 - ]吡唑 - 4,6 - (2,5) - 二酮的C - 6位高效形成碳 - 碳和碳 - 氮键的反应。该方法为合成各种1,6 - 二取代吡咯并[3,4 - ]吡唑 - 4,6 - (2,5) - 二酮提供了新途径。
