Department of Chemistry, College of Science, University of Guilan, University Campus 2, Rasht, Iran.
Comb Chem High Throughput Screen. 2021;24(1):155-163. doi: 10.2174/1386207323666200709170916.
In this work, we tried to introduce a non-toxic and stable organic compound named succinimide as a green and efficient organo-catalyst for the promotion of the synthesis of arylidene malononitrile and tetrahydrobenzo[b]pyran derivatives. Using this method led to a clean procedure to achieve these types of bioactive compounds without a specific purification step. The rate and yield of the reactions were excellent, and also succinimide showed acceptable reusability as the catalyst.
In a 25 mL round-bottom flask, [A: a mixture of aromatic aldehyde (1 mmol), malononitrile (1.1 mmol) and B: a mixture of aromatic aldehyde (1.0 mmol), malononitrile (1.1 mmol)] and succinimide (0.2 mmol) in H2O/ EtOH [5 mL (1:1)] was stirred at 80 °C for an appropriate time. After completion of the reaction, which was monitored by TLC [n-hexane-EtOAc (7:3)], the mixture was cooled to room temperature, and the solid product was filtered, washed several times with cold distilled water to obtain the corresponding pure product.
After the optimization of the conditions and amount of the catalyst, a series of aromatic aldehydes containing either-electron-donating or electron-withdrawing substituents were successfully used for both of the reactions. The reactions rates and yields under the selected conditions were excellent. The nature and electronic properties of the substituents had no obvious effect on the rate and yield of the reaction. Meanwhile, the catalyst showed acceptable reusability for these two reactions.
In this work, we have introduced Succinimide as a green and safe organo-catalyst for the efficient synthesis arylidene malononitrile and tetrahydrobenzo[b]pyran derivatives. The results showed that the catalyst had excellent efficiency in green aqueous media and also the reusability of the catalyst was good.
在这项工作中，我们试图引入一种无毒且稳定的有机化合物琥珀酰亚胺，作为一种绿色高效的有机催化剂，促进芳基亚甲基丙二腈和四氢苯并[b]吡喃衍生物的合成。使用这种方法可以在无需特定纯化步骤的情况下，以清洁的方式获得这些类型的生物活性化合物。反应的速率和产率都很高，而且琥珀酰亚胺作为催化剂也具有良好的可重复使用性。
在 25 mL 圆底烧瓶中，[A：芳香醛（1 mmol）、丙二腈（1.1 mmol）的混合物和 B：芳香醛（1.0 mmol）、丙二腈（1.1 mmol）的混合物]和琥珀酰亚胺（0.2 mmol）在 H2O/ EtOH [5 mL（1:1）]中搅拌，温度为 80°C，反应时间适当。反应完成后，通过 TLC [正己烷-乙酸乙酯（7:3）]监测，将混合物冷却至室温，将固体产物过滤，用冷蒸馏水多次洗涤，得到相应的纯产物。
在优化条件和催化剂用量后，一系列含有供电子或吸电子取代基的芳香醛成功地用于这两种反应。在所选择的条件下，反应速率和产率都很高。取代基的性质和电子性质对反应速率和产率没有明显影响。同时，该催化剂对这两种反应具有良好的可重复使用性。
在这项工作中，我们引入了琥珀酰亚胺作为一种绿色安全的有机催化剂，用于高效合成芳基亚甲基丙二腈和四氢苯并[b]吡喃衍生物。结果表明，该催化剂在绿色水相介质中具有优异的效率，并且催化剂的可重复使用性良好。
