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Introduction of Succinimide as A Green and Sustainable Organo-Catalyst for the Synthesis of Arylidene Malononitrile and Tetrahydrobenzo[b]pyran Derivatives.
Combinatorial Chemistry & High Throughput Screening ( IF 1.8 ) Pub Date : 2020-12-31 , DOI: 10.2174/1386207323666200709170916
Fariba Hassanzadeh 1 , Farhad Shirini 1 , Manouchehr Mamaghani 1 , Nader Daneshvar 1
Affiliation  

Aim and Objective: 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.

Materials and Methods: 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.

Results: 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.

Conclusion: 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.



中文翻译:

引入琥珀酰亚胺作为合成亚芳基丙二腈和四氢苯并 [b] 吡喃衍生物的绿色可持续有机催化剂。

目的与目的: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,用于促进亚芳基丙二腈和四氢苯并[b]吡喃衍生物的合成。使用这种方法可以通过清洁程序获得这些类型的生物活性化合物,而无需特定的纯化步骤。反应的速率和产率非常好,而且琥珀酰亚胺作为催化剂也表现出可接受的可重复使用性。

材料和方法: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)] 中的溶液在 80 °C 下搅拌适当的时间。反应完成后,TLC监测[正己烷-乙酸乙酯(7:3)],将混合物冷却至室温,过滤固体产物,用冷蒸馏水洗涤数次,得到相应的纯产品。

结果:优化催化剂的条件和用量后,一系列含有给电子或吸电子取代基的芳香醛均成功用于这两个反应。在所选条件下的反应速率和产率非常好。取代基的性质和电子性质对反应的速率和产率没有明显影响。同时,催化剂对这两个反应显示出可接受的重复使用性。

结论: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,用于有效合成亚芳基丙二腈和四氢苯并 [b] 吡喃衍生物。结果表明,该催化剂在绿色水性介质中具有优异的效率,且催化剂的重复使用性良好。

更新日期:2021-01-13
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