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新型一锅法三组分合成苯并呋喃衍生物斯特雷克反应:抗氧化活性研究。

A novel one-pot three-component synthesis of benzofuran derivatives Strecker reaction: Study of antioxidant activity.

机构信息

Department of Chemistry, Ardabil Branch, Islamic Azad University, Ardabil, Iran.

Department of Chemistry, Qaemshahr Branch, Islamic Azad University, Qaemshahr, Iran.

出版信息

Nat Prod Res. 2020 Apr;34(7):923-929. doi: 10.1080/14786419.2018.1542389. Epub 2018 Dec 26.

Abstract

A three-component Strecker-type reactions was applied for the synthesis of benzofuran derivatives through the reaction of 1-(6-hydroxy-2-isopropenyl-1-benzofuran-yl)-1-ethanone (euparin), primary amines and trimethylsilyl cyanide (TMSCN) in the presence of catalytic amount of ZnO-nanorods (ZnO-NR) and piperidine in acetonitrile at room temperature. The method has proved to be synthetically simple, and effective with high atom economy and yield. The catalyst also revealed significant reusability. Moreover, the antioxidant activity and free radical scavenging capacity of the newly synthesized such as , , and was screened using free radical scavenging 2,2-diphenyl-1-picrylhydrazyl (DPPH) and ferric reducing antioxidant power (FRAP) assays and compared with hydroxytoluene (BHT) and tert-butylhydroquinone (TBHQ). These compounds exhibit good DPPH radical scavenging and ferric reducing antioxidant power (FRAP) assays.

摘要

一种三组分Strecker 型反应被应用于苯并呋喃衍生物的合成,通过在催化量的 ZnO-纳米棒(ZnO-NR)和哌啶存在下,用 1-(6-羟基-2-丙烯基-1-苯并呋喃基)-1-乙酮(euparin)、伯胺和三甲基硅基氰化物(TMSCN)在乙腈中于室温下反应。该方法被证明具有合成简单、高效、原子经济性高和产率高的特点。该催化剂还表现出显著的可重复使用性。此外,新合成的抗氧化活性和自由基清除能力如 、 、 和 通过自由基清除 2,2-二苯基-1-苦基肼(DPPH)和铁还原抗氧化能力(FRAP)测定法进行筛选,并与羟基甲苯(BHT)和叔丁基对苯二酚(TBHQ)进行比较。这些化合物表现出良好的 DPPH 自由基清除和铁还原抗氧化能力(FRAP)测定法。

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