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Ultrasound-promoted green synthesis of pyrido[2,1-a]isoquinoline derivatives and studies on their antioxidant activity.
Combinatorial Chemistry & High Throughput Screening ( IF 1.8 ) Pub Date : 2020-12-31 , DOI: 10.2174/1386207323666200606212501
Shirin Sharafian 1 , Zinatossadat Hossaini 1 , Faramarz Rostami-Charati 1 , Mohammad A Khalilzadeh 1
Affiliation  

Aims & Objective: An efficient procedure for the synthesis of pyrido[2,1-a]isoquinoline derivatives in excellent yields was investigated using catalyst-free multicomponent reaction of phthaladehyde, methylamine, activated acetylenic compounds, alkyl bromides and triphenylphosphine in water under ultrasonic irradiation at room temperature. In addition, Diels- Alder reactions of pyrido[2,1-a]isoquinoline derivatives with activated acetylenic compounds under ultrasonic irradiation are investigated in two procedures. The advantages of this procedure compared to report methods are short time of reaction, high yields of product, easy separation of product, clean mixture of reaction and green media for performing reaction. In addition, because of having isoquinoline core in synthesized compounds, in this research antioxidant activity of some synthesized compounds was studied.

Materials and Methods: To a stirred mixture of phthalaldehyde 1 (2 mmol) and methylamine 2 (2 mmol) in water (3 mL) under ultrasonic irradiation was added to activated acetylenic compounds 4 after 20 min. Alkyl bromide 3 and triphenylphosphine 5 react in another pot in water (3 mL) under ultrasonic irradiation for 15 min. After this time, this mixture was added to the first pot. After completion of the reaction, the solid residue was separated by filtration and washed with Et2O to afforded pure title compound 6.

Results: In this work, generation of pyrido[2,1-a]isoquinoline derivatives 6 are performed using phthalaldehyde 1, methylamine 2, α-halo substituted carbonyls 3, activated acetylenic compounds 4 and triphenylphosphine 5 in water under ultrasonic irradiation condition at room temperature in excellent yield at short time.

Conclusion: In summary, multicomponent reaction of phthaladehyde, methylamine, activated acetylenic compounds, alkyl bromides and triphenylphosphine in water under ultrasonic irradiation at room temperature produced pyrido[2,1-a]isoquinoline derivatives in excellent yields. Also, Diels-Alder reaction of pyrido[2,1-a]isoquinoline derivatives with activated acetylenic compounds and triphenylphosphine under ultrasonic irradiation is investigated in two procedures. Also, the antioxidant activities of 6a, 6c, 6g and 6i were evaluated by DPPH radical scavenging and ferric reducing power analyzes. The compounds 6a exhibit excellent DPPH radical scavenging activity and FRAP compared to synthetic antioxidants BHT and TBHQ. The chief benefits of our method are high atom economy, green reaction conditions, higher yield, shorter reaction times, and easy work-up, which agree with some principles of green chemistry.



中文翻译:

超声促进吡啶并[2,1-a]异喹啉衍生物的绿色合成及其抗氧化活性研究。

目的与目的:采用无催化剂多组分反应,在超声波照射下,邻苯二甲醛、甲胺、活化炔属化合物、烷基溴和三苯基膦在水中的多组分反应以优异的收率合成吡啶并[2,1-a]异喹啉衍生物。在室温下。此外,在两个程序中研究了在超声辐射下吡啶并 [2,1-a] 异喹啉衍生物与活化的炔属化合物的 Diels-Alder 反应。与报道方法相比,该方法的优点是反应时间短、产物收率高、产物容易分离、反应混合物干净、反应介质绿色。此外,由于合成化合物中含有异喹啉核,

材料和方法: 20 分钟后,在超声照射下,将苯二醛 1 (2 mmol) 和甲胺 2 (2 mmol) 在水 (3 mL) 中的搅拌混合物加入到活化的炔属化合物 4 中。烷基溴 3 和三苯基膦 5 在另一个锅中的水 (3 mL) 中在超声波照射下反应 15 分钟。此后,将该混合物加入第一个罐中。反应完成后,过滤分离固体残留物并用Et2O洗涤,得到纯的标题化合物6。

结果:在这项工作中,使用邻苯二甲醛 1、甲胺 2、α-卤代羰基化合物 3、活化炔属化合物 4 和三苯膦 5 在室温超声照射条件下在水中生成吡啶并 [2,1-a] 异喹啉衍生物 6在短时间内以优异的温度产率。

结论:总之,邻苯二甲醛、甲胺、活化炔属化合物、烷基溴和三苯基膦在室温下超声辐照水中的多组分反应以优异的产率产生吡啶并[2,1-a]异喹啉衍生物。此外,在两个程序中研究了在超声辐射下吡啶并 [2,1-a] 异喹啉衍生物与活化的炔属化合物和三苯基膦的 Diels-Alder 反应。此外,通过 DPPH 自由基清除和铁还原能力分析评估了 6a、6c、6g 和 6i 的抗氧化活性。与合成抗氧化剂 BHT 和 TBHQ 相比,化合物 6a 表现出优异的 DPPH 自由基清除活性和 FRAP。我们方法的主要优点是原子经济性高、反应条件绿色、产率更高、反应时间更短、

更新日期:2021-01-13
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