硝基烷烃在C-N和C-S键形成反应中的酮合成等价物

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-04-24 DOI:10.1021/acs.orglett.5c00948

Shubham Tiwari, Guddeangadi N. Gururaja

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引用次数: 0

摘要

对具有稳定碳离子的2-硝基丙烷衍生物对潜在酮当量的umpolung策略进行了探索。改变硝基烷烃α-碳本征极性的结果是，在硝基官能团的相邻位置同时安装C-N键和C-S键。虽然相邻位置的硝基烷烃的电子偏压较差，但潜在的酮的形成有利于二硫-3-硫酮核心结构中C-S键的形成。该方法的应用也通过合成异噻唑-3-硫酮的氨基衍生物得到了证明。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Nitroalkanes as Ketone Synthetic Equivalents in C–N and C–S Bond Formation Reactions

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Nitroalkanes as Ketone Synthetic Equivalents in C–N and C–S Bond Formation Reactions

The umpolung strategy has been explored with 2-nitropropane derivatives featuring stabilized carbanion to latent ketone equivalents. The consequence of changing intrinsic polarity at the α-carbon of nitroalkanes induces simultaneous installation of the C–N bond at the geminal and C–S bond at the vicinal positions of the nitro functionality. Although the vicinal position of nitroalkanes bears poor electronic bias, the latent ketone formation facilitates C–S bond formation in the dithiole-3-thione core structure. The application of this methodology is also demonstrated with the synthesis of amino derivatives of isothiazole-3-thione.

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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.