NBS-Promoted Synthesis of Maleimides by Oxidative Dearomatization of Pyrroles: Mechanistic Investigations Using Online MS in Real-Time.

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-07-12 DOI:10.1021/acs.orglett.5c01976

Ankit Kumar,Pawan K Mishra,Abhijit Nandy,Ryan A Altman,Shibdas Banerjee,Akhilesh K Verma

引用次数: 0

Abstract

Oxidative dearomatization of pyrroles is an important organic transformation to deliver pharmaceutically important compounds, especially the synthesis of diaryl maleimides via the dearomatization of pyrroles has always been challenging. Herein, we report an unprecedented protocol for synthesizing functionalized maleimides by NBS-promoted oxidative dearomatization of 2,3,4-trisubstituted pyrroles. The reaction proceeds via three sequential reactions: dearomatization, oxidation, and detosylation. The use of online EI mass spectrometry has enabled the mechanistic analysis of the reaction by capturing several short-lived intermediates and monitoring the progress of the reaction in real-time.

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nbs催化吡罗氧化脱芳合成马来酰亚胺：实时在线质谱研究

吡咯氧化脱芳是传递具有重要药理意义的化合物的重要有机转化，特别是通过吡咯脱芳合成二芳基马来酰亚胺一直是一个具有挑战性的问题。在此，我们报道了一个前所未有的方案，通过nbs促进2,3,4-三取代吡咯氧化脱芳合成功能化马来酰亚胺。该反应通过三个连续反应进行：脱芳化、氧化和脱烷基。在线EI质谱的使用通过捕获几个短寿命中间体和实时监测反应的进展，使反应的机理分析成为可能。

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.