铁（III）介导的叔烯酰胺与二烯酰胺的亲核级联环化以构建3-硒-2-吡啶酮

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-01-12 DOI:10.1021/acs.orglett.4c04446

Xin-Ming Xu, Jiping Wang, Xiaoxu Chen, Zhongyuan Zhao, Qian Liu, Miao Tian, Kai Sun

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引用次数: 0

摘要

研究了一种铁（III）介导的n -丙酰酰胺与多种二硒化合物的亲核级联环化反应，为构建硒杂环提供了一种有效途径。一项机制研究表明，级联过程包括选择性地将二硒化物加成到C≡C键上，生成硒离子，然后是叔胺的胺碳分子内亲核攻击。利用该工艺，成功合成了多种3-硒-2-吡啶酮，具有良好的官能团相容性和简单的操作。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Iron(III)-Mediated Nucleophilic Cascade Cyclization of Tertiary Enamides with Diselenides for the Construction of 3-Seleno-2-pyridones

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Iron(III)-Mediated Nucleophilic Cascade Cyclization of Tertiary Enamides with Diselenides for the Construction of 3-Seleno-2-pyridones

An iron(III)-mediated nucleophilic cascade cyclization of N-propiolyl enamides with various diselenides was developed, which provides an efficient way to construct seleno-heterocycles. A mechanism study shows that the cascade process involves the selective addition of diselenides to the C≡C bond generating a seleniranium ion, followed by an intramolecular nucleophilic attack of enaminic carbon of tertiary enamide. Utilizing this protocol, a variety of 3-seleno-2-pyridones were successfully synthesized featuring good functional group compatibility and simple operation.

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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.