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串联 Knoevenagel [4+1] 环加成-缩合-aza-Friedel-Crafts 分子内环化反应:一种可调谐荧光吲哚嗪四环的 4 中心 3 组分反应。

Sequential Knoevenagel [4+1] Cycloaddition-Condensation-Aza-Friedel-Crafts Intramolecular Cyclization: A 4-Center-3-Component Reaction Toward Tunable Fluorescent Indolizine Tetracycles.

机构信息

Department of Chemistry & Biochemistry, College of Science, The University of Arizona, Tucson, Arizona 85721, United States.

Department of Pharm./Tox., College of Pharmacy, The University of Arizona, Tucson, Arizona 85721, United States.

出版信息

J Org Chem. 2021 Dec 17;86(24):17550-17559. doi: 10.1021/acs.joc.1c01280. Epub 2021 Nov 24.

Abstract

A two-step multicomponent reaction oxidation protocol is reported herein, which affords novel tunable fluorescent tetracyclic indolizines. The procedure involves a novel 4-center-3-component reaction, which proceeds via a sequential Knoevenagel condensation, [4+1] cycloaddition, and imine condensation to afford imino-indolizines. Products then undergo cyclization and are oxidized to afford fluorescent tetracycles, which are readily tunable through modification of diversity elements.

摘要

本文报道了一种两步多组分反应氧化方案,可提供新型可调谐荧光四环吲嗪。该方法涉及一种新颖的 4 中心-3 组分反应,通过顺序的 Knoevenagel 缩合、[4+1]环加成和亚胺缩合得到亚氨基吲嗪。然后产物进行环化并被氧化得到荧光四环,通过改变多样性元素可以很容易地进行修饰。

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