通过环己二酮切割-熔合策略重建氟化二氢吡啶并[1,2-a]吲哚酮的合成

IF 4.4 2区化学 Q2 CHEMISTRY, APPLIED

Advanced Synthesis & Catalysis Pub Date : 2024-10-28 DOI:10.1002/adsc.202401037

Hideyasu China, Yusuke Yoto, Hirotaka Sasa, Kotaro Kikushima, Toshifumi Dohi

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引用次数: 0

摘要

我们描述了一种氟化裂环反应，该反应在无机碳酸盐（Cs2CO3 或 K2CO3）存在下，于室温一小时内在甲醇中使用 N-氟苯磺酰亚胺（NFSI）断裂带有芳基的环状 β-二酮中的 C-C 键。生成的含正硝基芳基的氟化酮酸酯在 K2CO3 的存在下，通过使用 B2(OH)4 进行还原环化，然后进行酰胺化反应，转化为氟化二氢吡啶并[1,2-a]吲哚酮（DHPIs）。这种 "从切割到融合 "的策略可以从相对简单的环己二酮重新合成有价值的融合杂环。

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Reconstructive synthesis of fluorinated dihydropyrido[1,2-a]indolones by a cyclohexadione cut-to-fuse strategy

We describe a fluorinative ring-cleavage reaction that breaks C–C bonds in cyclic β-diketones bearing aryl moiety using N-fluorobenzenesulfonimide (NFSI) in the presence of inorganic carbonates (Cs2CO3 or K2CO3) in methanol at room temperature within one hour. Generated fluorinated keto acid esters bearing ortho-nitro aryl groups were transformed into fluorinated dihydropyrido[1,2-a]indolones (DHPIs) via reductive cyclization using B2(OH)4 followed by amidation in the presence of K2CO3. This "cut-to-fuse" strategy enables the reconstructive synthesis of valuable fused heterocycles from relatively simple cyclohexadione.

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来源期刊

Advanced Synthesis & Catalysis 化学-应用化学

CiteScore

9.40

自引率

7.40%

发文量

447

审稿时长

1.8 months

期刊介绍： Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry. The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.