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通过多组分反应实现黄烷酮电子等排体的区域和化学选择性合成:氢键和溶剂效应的协同作用

Regio- and chemoselective synthesis of flavanone isosteres via multicomponent reactions: synergistic role of hydrogen bonding and solvent effects.

作者信息

Zhang Li-Xin, Tang Zi-Yi, Liu Xin-Yue, Chen Xing-Yu, Jia Shi-Qi, Jiang Xing-Wei, Gao Xin-Yan, Xu Jia, Lei Jie

机构信息

College of Pharmacy, National and Local Joint Engineering Research Center of Targeted and Innovative Therapeutics, Chongqing Key Laboratory of Kinase Modulators As Innovative Medicine, Chongqing University of Arts and Sciences, Chongqing, 402160, China.

College of Agricultural and Forestry Sciences, Chongqing Three Gorges Vocational College, Chongqing, 404155, China.

出版信息

Mol Divers. 2025 Mar 26. doi: 10.1007/s11030-025-11151-4.

Abstract

Given the prevalence and significance of flavanones, we present a regio- and chemoselective approach for the synthesis of flavanone isosteres. This method is facilitated by the synergistic effects of hydrogen bonding and solvent interactions. Notably, this novel multicomponent reaction employs commercially available starting materials, operates without the need for catalysts, and achieves high levels of regio- and chemoselectivity under mild conditions. The protocol exhibits excellent tolerance for complex substrates, including those derived from Linagliptin and Cholesterol. Furthermore, this robust synthetic method not only surpasses the limitations of traditional approaches but also aligns with the principles of green chemistry.

摘要

鉴于黄烷酮的普遍性和重要性,我们提出了一种区域和化学选择性的方法来合成黄烷酮类似物。这种方法得益于氢键和溶剂相互作用的协同效应。值得注意的是,这种新型多组分反应使用市售起始原料,无需催化剂即可运行,并在温和条件下实现了高水平的区域和化学选择性。该方案对复杂底物表现出优异的耐受性,包括那些源自利格列汀和胆固醇的底物。此外,这种稳健的合成方法不仅克服了传统方法的局限性,而且符合绿色化学的原则。

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