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室温下以[H-DABCO][HSO]离子液体为绿色催化剂的六氢喹啉合成串联反应方案

Tandem Protocol of Hexahydroquinoline Synthesis Using [H-DABCO][HSO] Ionic Liquid as a Green Catalyst at Room Temperature.

作者信息

Sahiba Nusrat, Sethiya Ayushi, Teli Pankaj, Agarwal Shikha

机构信息

Synthetic Organic Chemistry Laboratory, Department of Chemistry, Mohanlal Sukhadia University (MLSU), Udaipur 313001, India.

出版信息

ACS Omega. 2023 Feb 6;8(6):5877-5884. doi: 10.1021/acsomega.2c07672. eCollection 2023 Feb 14.

Abstract

Green, eco-benign, and sustainable synthesis is paramount in present chemistry. Here, a facile, efficient, and [H-DABCO][HSO] ionic-liquid-catalyzed one-pot multicomponent synthesis of hexahydroquinolines was reported under ambient reaction conditions. The reaction of 1,3-dicarbonyls, malononitrile, and ammonium acetate with various aldehydes in the presence of an ionic liquid catalyst and EtOH solvent at room temperature afforded excellent yields (76-100%) of hexahydroquinolines under a short reaction time (5-15 min). Mild reaction conditions, broad substrate scope (28 derivatives), and column-chromatography-free synthesis with excellent catalytic efficiency and good recyclability rendered this protocol superior and practical. The greenness of the present method was assessed through eco-score and E-factor. The significant results in gram-scale synthetic conditions validate its applicability in industries as well as academia in the near future.

摘要

绿色、环境友好且可持续的合成在当今化学领域至关重要。在此,报道了一种在环境反应条件下,由[H-DABCO][HSO]离子液体催化的1,3-二羰基化合物、丙二腈和醋酸铵与各种醛的简便、高效一锅多组分合成六氢喹啉的方法。在离子液体催化剂和乙醇溶剂存在下,1,3-二羰基化合物、丙二腈、醋酸铵与各种醛在室温下反应,在短反应时间(5 - 15分钟)内可获得优异产率(76 - 100%)的六氢喹啉。温和的反应条件、广泛的底物范围(28种衍生物)以及无需柱色谱的合成方法,具有优异的催化效率和良好的可循环性,使得该方法具有优越性和实用性。通过生态评分和E因子评估了本方法的绿色程度。克级合成条件下的显著结果证实了其在不久的将来在工业和学术界的适用性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/68eb/9933228/9aa9619bea92/ao2c07672_0007.jpg

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