Visible-Light-Induced Strain-Release [2π + 2σ] Cycloaddition of Bicyclo[1.1.0]butanes with N-Vinylamides: Access to Highly Functionalized Bicyclo[2.1.1]hexanes

IF 4.7 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2026-10-19 DOI:10.1021/acs.orglett.6c03781

Xiao-Yu He,Piao-Piao Yang-Liu,Man Deng,Kun Shen,Dan Liu,You-Quan Zou

引用次数: 0

Abstract

The development of modular and efficient routes to functionalized bicyclo[2.1.1]hexanes (BCHs) is of considerable importance in synthetic and medicinal chemistry. Herein, we disclose a photocatalytic [2π + 2σ] cycloaddition between bicyclo[1.1.0]butanes (BCBs) and N-vinylamides that enables the direct and regioselective construction of 2-aminobicyclo[2.1.1]hexanes (2-aminoBCHs). Biological evaluation revealed that some of the BCH derivatives exhibit potent activity against A549 (lung cancer) and MDA-MB-231 (triple negative breast cancer) cell lines, outperforming their aromatic bioisosteres.

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双环[1.1.0]丁烷与n-乙烯酰胺的可见光诱导释放[2π + 2σ]环加成：获得高功能化双环[2.1.1]己烷

开发模块化和高效的功能化双环[2.1.1]己烷（BCHs）路线在合成和药物化学中具有相当重要的意义。在此，我们揭示了在双环[1.1.0]丁烷（BCBs）和n -乙烯酰胺之间的光催化[2π + 2σ]环加成反应，使得2-氨基双环[2.1.1]己烷（2-氨基obchs）的直接和区域选择性构建成为可能。生物学评价显示，一些BCH衍生物对A549（肺癌）和MDA-MB-231（三阴性乳腺癌）细胞系具有较强的活性，优于其芳香生物同位体。

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.