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ZnO-nanorods Promoted Synthesis of α-amino Nitrile Benzofuran Derivatives using One-pot Multicomponent Reaction of Isocyanides.
Combinatorial Chemistry & High Throughput Screening ( IF 1.8 ) Pub Date : 2020-05-01 , DOI: 10.2174/1386207323666200219124625
Asef H Najar 1 , Zinatossadat Hossaini 1 , Shahrzad Abdolmohammadi 2 , Daryoush Zareyee 1
Affiliation  

Aims and Objective: In this work ZnO-nanorod (ZnO-NR) as reusable catalyst promoted Strecker-type reaction of 2,4-dihydroxyacetophenone, isopropenylacetylene, trimethylsilyl cyanide (TMSCN), primary amines and isocyanides at ambient temperature under solvent-free conditions and produced α-amino nitriles benzofuran derivatives in high yields. These synthesized compounds may have antioxidant ability.

Materials and Methods: ZnO-NRs in these reactions were prepared according to reported article. 2,4-dihydroxyacetophenone 1 (2 mmol) and isopropenylacetylene 2 (2 mmol) were mixed and stirred for 30 min in the presence of ZnO-NR (10 mol%) under solvent-free conditions at room temperature. After 30 min, primary amine 3 (2 mmol) was added to the mixture gently and the mixture was stirred for 15 min. After this time TMSCN 4 (2 mmol) was added to the mixture and stirred for 15 min. After completion of the reaction, as indicated by TLC, isocyanides 5 was added to mixture in the presence of catalyst.

Results: In the first step of this research, the reaction of 2,4-dihydroxyacetophenone 1, isopropenylacetylene 2, methyl amine 3a, trimethylsilyle cyanide 4 and tert-butyl isocyanides 5a was used as a sample reaction to attain the best reaction conditions. The results showed this reaction performed with catalyst and did not have any product without catalyst after 12 h.

Conclusion: In conclusion, we investigate multicomponent reaction of 2,4-dihydroxyacetophenone 1, isopropenylacetylene 2, primary amines 3, trimethylsilyl cyanide 4 and isocyanides along with ZnO-NRs as reusable catalyst at room temperature under solvent-free conditions which generates α-amino nitrile benzofuran derivatives in high yields. The advantages of our method are high atom economy, green reaction conditions, higher yield, shorter reaction times, and easy work-up, which are in good agreement with some principles of green chemistry. The compounds 8c exhibit excellent DPPH radical scavenging activity and FRAP compared to synthetic antioxidants BHT and TBHQ.



中文翻译:

ZnO-纳米螯合物通过异氰酸酯的一锅多组分反应促进了α-氨基腈苯并呋喃衍生物的合成。

目的和目的:在可重复使用的催化剂中,ZnO-纳诺洛德(ZnO-NR)在环境温度和无溶剂条件下,促进了2,4-二羟基苯乙酮,异丙烯基乙炔,三甲基甲硅烷基氰化物(TMSCN),伯胺和异氰酸酯的Strecker型反应。并以高收率生产了α-氨基腈苯并呋喃衍生物。这些合成的化合物可以具有抗氧化能力。

材料和方法:这些反应中的ZnO-NRs是根据报道的文章制备的。混合2,4-二羟基苯乙酮1(2 mmol)和异丙烯基乙炔2(2 mmol),在无溶剂条件下于室温在ZnO-NR(10 mol%)下搅拌30分钟。30分钟后,将伯胺3(2 mmol)缓慢添加至混合物中,并将混合物搅拌15分钟。此时间之后,将TMSCN 4(2mmol)添加至混合物中,并搅拌15分钟。反应完成后,如TLC所示,在催化剂存在下将异氰酸酯5加入混合物中。

结果:在本研究的第一步中,将2,4-二羟基苯乙酮1,异丙烯基乙炔2,甲胺3a,三甲基甲硅烷基氰化物4和叔丁基异氰化物5a的反应用作样品反应以获得最佳反应条件。结果表明该反应用催化剂进行,并且在没有催化剂的情况下12小时后没有任何产物。

结论:总之,我们在室温下无溶剂条件下研究了2,4-二羟基苯乙酮1,异丙烯基乙炔2,伯胺3,三甲基甲硅烷基氰化物4和异氰化物与ZnO-NRs的可重用催化剂的多组分反应,该反应可生成α-氨基腈苯并呋喃衍生物的收率很高。该方法的优点是原子经济性高,绿色反应条件高,收率高,反应时间短,后处理容易,这与绿色化学的某些原理非常吻合。与合成抗氧化剂BHT和TBHQ相比,化合物8c具有出色的DPPH自由基清除活性和FRAP。

更新日期:2020-05-01
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