Lewis Acid-Catalyzed Domino Inverse Electron-Demand Diels–Alder/Thermal Ring Expansion Reaction for the Synthesis of Arene-Annulated Eight-Membered Nitrogen Heterocycles

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-05-01 DOI:10.1021/acs.orglett.5c01150

Michel Große, Christopher M. Leonhardt, Patrick A. R. Campbell, Hermann A. Wegner

引用次数: 0

Abstract

A domino inverse electron-demand Diels–Alder reaction/thermal ring expansion sequence was developed to enable the one-step synthesis of arene-annulated eight-membered nitrogen heterocycles from readily available aromatic 1,2-diazines. A boron-based, bidentate Lewis acid catalyst facilitates the initial cycloaddition of Boc-protected 2-azetine with various electron-poor and electron-rich phthalazines. The subsequent electrocyclic ring expansion furnishes azocines fused to differently substituted aromatics, a structural motif that holds vast potential for further derivatization.

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Lewis酸催化的多米诺逆电按需diols - alder /热扩环反应合成芳烃环八元氮杂环

建立了多米诺骨牌逆电按需diols - alder反应/热扩环序列，使芳烃环八元氮杂环的一步合成成为可能。硼基双齿刘易斯酸催化剂促进了boc保护的2-azetine与各种贫电子和富电子的酞嗪的初始环加成。随后的电环扩张使偶氮嘧啶与不同取代的芳烃融合，这种结构基序具有进一步衍生化的巨大潜力。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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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.