丙烯基苯并恶嗪酮和4-硝基异恶唑的溶剂控制脱芳反应：功能化喹啉和融合四氢喹啉的发散合成

IF 4.7 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2026-10-19 DOI:10.1021/acs.orglett.6c04302

Ran Wang,Jianren Dai,Zhaorui Lv,Xintong Yuan,Wei Qin,Ruixue Wang,Biming Mao,Chang Wang,Hongchao Guo,Chunhao Yuan

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引用次数: 0

摘要

我们报道了一种有效的溶剂调节pd催化的烯丙基苯并恶嗪酮和4-硝基异恶唑之间的脱芳反应。在二氯甲烷中，该转化遵循级联的分子内环化/分子间去芳香迈克尔加成顺序，以高达85%的收率和>20:1的dr生成功能化喹啉。在二氯甲烷中，该反应通过去芳香的形式环化[4 + 2]进行，很容易得到收率高达83%和dr为>20:1的融合四氢喹啉产物。这项工作也构成了烷基烯- π-烯丙基钯偶极子的脱芳反应性的第一个报告。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Solvent-Controlled Pd-Catalyzed Dearomative Reactions of Allenyl Benzoxazinones and 4-Nitroisoxazoles: Divergent Synthesis of Functionalized Quinolines and Fused Tetrahydroquinolines

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Solvent-Controlled Pd-Catalyzed Dearomative Reactions of Allenyl Benzoxazinones and 4-Nitroisoxazoles: Divergent Synthesis of Functionalized Quinolines and Fused Tetrahydroquinolines

We report an efficient solvent-modulated Pd-catalyzed dearomatization reaction between allenyl benzoxazinones and 4-nitroisoxazoles. When carried out in Diox, the transformation follows a cascade intramolecular cyclization/intermolecular dearomative Michael addition sequence, producing functionalized quinolines in up to 85% yield with >20:1 dr. In dichloromethane, the reaction proceeds through a dearomative formal [4 + 2] annulation instead, readily furnishing fused tetrahydroquinoline products with up to 83% yield and dr of >20:1. This work also constitutes the first report of dearomative reactivity derived from alkylidene−π-allylpalladium dipoles.

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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.