Unexpected Discovery of an Inverse‐Electron‐Demand (5 + 4) Cycloaddition of Oxidopyridinium With Trifluoromethylated o ‐Quinone Methide Yielding a Bridged N, O‐Acetal Scaffold

IF 4 2区化学 Q2 CHEMISTRY, APPLIED

Advanced Synthesis & Catalysis Pub Date : 2026-04-27 DOI:10.1002/adsc.70470

Yuto Ide, Takeshi Yasui, Yoshihiko Yamamoto

引用次数: 0

Abstract

We investigated the reaction of in situ generated 1‐(pyrimidin‐2‐yl)‐3‐oxidopyridiniums with a trifluoromethylated o ‐quinone methide and discovered that unexpected bridged N‐heterocycles bearing an N, O‐acetal moiety were predominantly formed via a (5 + 4) cycloaddition occurring at the 2‐ and 6‐positions of the oxidopyridinium ring. To rationalize the unusual regioselectivity, a non‐concerted mechanism was proposed based on density functional theory calculations.

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意外发现氧化吡啶与三氟甲基化的o -醌甲基的反电子需求（5 + 4）环加成，生成桥接N， o -缩醛支架

我们研究了原位生成的1‐（嘧啶‐2‐基）‐3‐氧化吡啶与三氟甲基化的邻醌的反应，发现含有N， o -缩醛的桥接N -杂环主要是通过发生在氧化吡啶环的2‐和6‐位置的（5 + 4）环加成形成的。基于密度泛函理论的计算，提出了一种非协调机制来解释不同寻常的区域选择性。

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

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.