含有酰胺片段的异麦芽酮醇衍生物在碱促进下级联再生成取代的 3-(1-羟基亚乙基)四酸。

IF 2.2 4区 化学 Q2 CHEMISTRY, ORGANIC Beilstein Journal of Organic Chemistry Pub Date : 2024-10-14 eCollection Date: 2024-01-01 DOI:10.3762/bjoc.20.217
Andrey Nikolaevich Komogortsev, Constantine Vyacheslavovich Milyutin, Boris Valerievich Lichitsky
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引用次数: 0

摘要

研究人员首次研究了侧链中含有酰胺片段的异麦芽酮醇衍生物的再化学反应。结果表明,所研究的过程会产生带有吡咯烷酮分子的取代四元酸。1,1'- 碳酰二咪唑和 DBU 的应用是实施所考虑反应的必要条件。基于已完成的研究,我们详细阐述了合成多种 (3E,5E)-3-(1-羟基亚乙基)-5-(5-氧代吡咯烷-2-亚基)呋喃-2,4(3H,5H)-二酮的通用方法。该方法的优点是起始化合物容易获得,目标产物的分离简单,无需色谱纯化。通过羟基亚乙基片段的进一步转化,证明了所制备的四元酸的合成用途。通过 X 射线分析,确认了所获得的一种四元酸和一种衍生产物的结构。
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Base-promoted cascade recyclization of allomaltol derivatives containing an amide fragment into substituted 3-(1-hydroxyethylidene)tetronic acids.

For the first time, recyclization of allomaltol derivatives with an amide fragment in the side chain were investigated. It was shown that the studied process leads to substituted tetronic acids bearing a pyrrolidinone moiety. The application of 1,1'-carbonyldiimidazole and DBU is necessary for implementation of the considered reaction. Based on the performed research a general method for the synthesis of a wide range of (3E,5E)-3-(1-hydroxyethylidene)-5-(5-oxopyrrolidin-2-ylidene)furan-2,4(3H,5H)-diones was elaborated. The advantages of the presented protocol are easily available starting compounds and simple isolation of the target products without chromatographic purification. The synthetic utility of the prepared tetronic acids was demonstrated by further transformations at the hydroxyethylidene fragment. The structures of one obtained tetronic acid and one product of derivatization were confirmed by X-ray analysis.

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来源期刊
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.
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