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用于更清洁地合成3,4-二氢嘧啶-2-(1)-酮的超高性能纤维负载铁基离子液体

Ultrahigh-Performance Fiber-Supported Iron-Based Ionic Liquid for Synthesizing 3,4-Dihydropyrimidin-2-(1)-ones in a Cleaner Manner.

作者信息

Zhang Tian, Shi Xian-Lei, Hu Qianqian, Gong Honghui, Shi Keren, Li Zhenhua

机构信息

College of Chemistry and Chemical Engineering, Henan Polytechnic University, Jiaozuo, Henan 454003, P. R. China.

State Key Laboratory of High-Efficiency Utilization of Coal and Green Chemical Engineering, Ningxia University, Yinchuan, Ningxia 750021, P. R. China.

出版信息

Langmuir. 2024 May 7;40(18):9579-9591. doi: 10.1021/acs.langmuir.4c00332. Epub 2024 Apr 24.

Abstract

Herein, a fiber-supported iron-based ionic liquid as a type of fibrous catalyst has been developed for the synthesis of bioactive 3,4-dihydropyrimidin-2-(1)-ones (DHPMs) via three-component Biginelli reactions in a cleaner manner. The described fibrous catalyst was obtained from the commercially available polyetheretherketone (PEEK) fiber by postfunctionalization processes and was characterized and analyzed in detail by means of diversified technologies. Furthermore, the fiber-supported iron-based ionic liquids could mediate the classical three-component Biginelli reactions to proceed smoothly to gain a variety of substituted DHPMs with yields of up to 99%. The superior catalytic activities of the fibrous catalyst were ascribed to the quasi-homogeneous medium by ionic liquids generated in the surface layer of the PEEK fiber, which could afford an appropriate reaction zone and could further be available for the aggregation of substrates to facilitate the three-component reaction. Notably, the fibrous catalyst is available for recycling over 10 runs just by a pair of tweezers, and the operational procedure was capable of enlarging the catalytic system to the gram-scale without any performance degradation, which provided a cleaner manner to take advantage of the iron-based catalyst in organic synthesis with potential industrialization prospects.

摘要

在此,一种纤维负载的铁基离子液体作为一种纤维状催化剂被开发出来,用于通过三组分Biginelli反应以更清洁的方式合成生物活性3,4-二氢嘧啶-2-(1)-酮(DHPMs)。所述纤维状催化剂是通过后功能化过程从市售的聚醚醚酮(PEEK)纤维获得的,并通过多种技术进行了详细的表征和分析。此外,纤维负载的铁基离子液体可以介导经典的三组分Biginelli反应顺利进行,以获得各种取代的DHPMs,产率高达99%。纤维状催化剂的优异催化活性归因于PEEK纤维表面层中离子液体产生的准均相介质,其可以提供合适的反应区域,并且可以进一步用于底物的聚集以促进三组分反应。值得注意的是,纤维状催化剂仅用一把镊子就可以循环使用10次以上,并且该操作程序能够将催化体系扩大到克级规模而不会有任何性能下降,这为在有机合成中利用铁基催化剂提供了一种更清洁的方式,具有潜在的工业化前景。

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