苯酚衍生物电化学脱芳合成恶唑-螺环己二酮

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters Pub Date : 2025-04-25 DOI:10.1016/j.tetlet.2025.155622

Long-Hao Zhu , Yuan-Zheng Cheng , Shu-Li You

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引用次数: 0

摘要

恶唑啉和螺环己二酮部分普遍存在于天然产物和生物活性分子中。在此，我们报道了一种利用酰胺侧链作为亲核试剂，通过电化学介导的酚衍生物氧化去芳化合成恶唑啉-螺环己二烯酮的有效方法。这种方法的特点是采用阳极氧化策略，避免了对传统氧化剂的需要。以中等至优异的收率（15 - 97%）可制得各种恶唑-螺环己二烯酮。循环伏安实验表明，溶剂在这一转变过程中起着至关重要的作用，该反应涉及两个连续的单电子转移事件。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Synthesis of Oxazoline-spirocyclohexadienone via Electrochemical Dearomatization of Phenol Derivatives

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Synthesis of Oxazoline-spirocyclohexadienone via Electrochemical Dearomatization of Phenol Derivatives

Oxazoline and spirocyclohexadienone moieties are prevalent in natural products and biologically active molecules. Herein, we report an efficient method for the synthesis of oxazoline-spirocyclohexadienones via electrochemistry-mediated oxidative dearomatization of phenol derivatives, utilizing amide side chains as nucleophiles. This approach features the employment of anodic oxidation strategy, circumventing the need for traditional oxidizing agents. A diverse range of oxazoline-spirocyclohexadienones are obtained in moderate to excellent yields (15–97 %). Cyclic voltammetry experiments reveal that the solvent plays a crucial role in this transformation and this reaction involves two consecutive single-electron transfer events.

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来源期刊

Tetrahedron Letters 化学-有机化学

CiteScore

3.50

自引率

5.60%

发文量

521

审稿时长

28 days

期刊介绍： Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.