[3 + 2]甲基硫代甲酰基与各种芳基唑酮环加成合成7-噻亚-3-氮杂螺[4.4]壬-4-酮。

IF 2.1 4区化学 Q2 CHEMISTRY, ORGANIC

Beilstein Journal of Organic Chemistry Pub Date : 2025-09-05 eCollection Date: 2025-01-01 DOI:10.3762/bjoc.21.141

Daniil I Rudik, Irina V Tiushina, Anatoly I Sokolov, Alexander Yu Smirnov, Alexander R Romanenko, Alexander A Korlyukov, Andrey A Mikhaylov, Mikhail S Baranov

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引用次数: 0

摘要

甲基硫代甲酰基很容易由氯甲基（三甲基硅基）甲基硫醚通过氟的作用生成，用于芳基-唑酮合成螺环衍生物。研究了相应的四种杂环化合物。得到了一系列7-thia-3-azaspiro[4.4]nonan-4- 1，产率从17%到99%不等。立体化学研究表明，单顺式或反式立体异构体的选择性形成，取决于所使用的杂环核心。

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[3 + 2] Cycloaddition of thioformylium methylide with various arylidene-azolones in the synthesis of 7-thia-3-azaspiro[4.4]nonan-4-ones.

Thioformylium methylide, which is readily generated from chloromethyl(trimethylsilyl)methyl sulfide by the action of fluoride, is used for the synthesis of spirocyclic derivatives from arylidene-azolones. Four types of the corresponding heterocycles have been studied. A series of 7-thia-3-azaspiro[4.4]nonan-4-ones was obtained with yields varying from 17 to 99%. The stereochemical study revealed selective formation of single either cis or trans stereoisomers, dependent on the heterocycle core used.

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来源期刊

Beilstein Journal of Organic Chemistry 化学-有机化学

CiteScore

4.90

自引率

3.70%

发文量

167

审稿时长

1.4 months

期刊介绍： The Beilstein Journal of Organic Chemistry is an international, peer-reviewed, Open Access journal. It provides a unique platform for rapid publication without any charges (free for author and reader) – Platinum Open Access. The content is freely accessible 365 days a year to any user worldwide. Articles are available online immediately upon publication and are publicly archived in all major repositories. In addition, it provides a platform for publishing thematic issues (theme-based collections of articles) on topical issues in organic chemistry. The journal publishes high quality research and reviews in all areas of organic chemistry, including organic synthesis, organic reactions, natural product chemistry, structural investigations, supramolecular chemistry and chemical biology.