多自串联反应获取位点特异性功能化三环呋喃[3,2-c]香豆素和萘[2,3-b]呋喃-4,9-二酮

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-04-24 DOI:10.1021/acs.orglett.5c00811

Xiang Liu, Hexiang Wang, Dongrong Lin, Zhen Lin, Qiye Chen, Baofu Zhu, Hua Cao

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引用次数: 0

摘要

报道了以4-羟基香豆素/4-羟基-2-吡酮、ynals和亚硫酸钠为原料，通过一步形成C-C、C-O和C-S键，构建位点特异性三环呋喃[3,2-c]香豆素的三组分多自串联反应。该级联反应在简单的反应条件下，以中等到较高的产率高效地制备了多种稀有的c -2功能化呋喃[3,2-c]香豆素。此外，该方法可以扩展到涉及2-羟基-1,4-萘醌，ynals和亚硫酸钠的三组分偶联，产生三环萘[2,3-b]呋喃-4,9-二酮衍生物。值得注意的是，羰基和ynals的α-位置在特定的多自串联反应中充当C-2合成子，使上述两种类型的多组分转化成为可能。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Multi-Auto-Tandem Reaction to Access Site-Specific Functionalized Tricyclic Furo[3,2-c]coumarins and Naphtho[2,3-b]furan-4,9-diones

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Multi-Auto-Tandem Reaction to Access Site-Specific Functionalized Tricyclic Furo[3,2-c]coumarins and Naphtho[2,3-b]furan-4,9-diones

A three-component multi-auto-tandem reaction for the construction of site-specific tricyclic furo[3,2-c]coumarins via the formation of C–C, C–O, and C–S bonds in one step from 4-hydroxycoumarins/4-hydroxy-2-pyrones, ynals, and sodium sulfinates is reported. This cascade reaction efficiently produces a variety of rare C-2-functionalized furo[3,2-c]coumarins in moderate to good yields under straightforward reaction conditions. Furthermore, this protocol can be extended to a three-component coupling involving 2-hydroxy-1,4-naphthoquinone, ynals, and sodium sulfinates, yielding tricyclic naphtho[2,3-b]furan-4,9-dione derivatives. Notably, the carbonyl group and the α-position of ynals act as C-2 synthons in the specific multi-auto-tandem reaction, enabling the two aforementioned types of multicomponent transformations.

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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.