利用3-亚甲基异吲哚酮作为原位反应中间体合成四取代碳中心

IF 2.7 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry Pub Date : 2025-06-10 DOI:10.1002/ajoc.202500562

Arben Beriša, Filip Duplić, Marko Purić, Matija Gredičak, Nikola Topolovčan

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引用次数: 0

摘要

在这项研究中，我们描述了一个操作简单的结构四取代碳中心利用原位形成的3-亚甲基异吲哚酮作为反应中间体。酸催化异吲哚酮基丙炔醇的Meyer-Schuster重排，然后是分子间Friedel-Crafts烷基化，组装3,3-二取代异吲哚酮，这是许多生物活性化合物中发现的重要结构基序。对构建块的结构变化高度惰性，这种强大的转化允许快速建立具有内嵌异吲哚酮核心的化合物库。此外，活化中间体的原位形成允许选择性地安装各种结构特征。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Exploiting 3-Methyleneisoindolinones as In Situ Generated Reactive Intermediates in the Synthesis of Tetrasubstituted Carbon Center

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Exploiting 3-Methyleneisoindolinones as In Situ Generated Reactive Intermediates in the Synthesis of Tetrasubstituted Carbon Center

In this study, we describe the operationally simple construction of a tetrasubstituted carbon center utilizing in situ formation of 3-methyleneisoindolinones as reactive intermediates. An acid-catalyzed Meyer–Schuster rearrangement of isoindolinone-based propargylic alcohols followed by an intermolecular Friedel–Crafts alkylation assembles the 3,3-disubstituted isoindolinones, an important architectural motif found in numerous biologically active compounds. Highly inert to structural changes in building blocks, this robust transformation allows the quick build-up of a library of compounds with an embedded isoindolinone core. In addition, the in situ formation of the activated intermediate allows a selective installation of various structural characteristics .

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来源期刊

Asian Journal of Organic Chemistry CHEMISTRY, ORGANIC-

CiteScore

4.70

自引率

3.70%

发文量

372

期刊介绍： Organic chemistry is the fundamental science that stands at the heart of chemistry, biology, and materials science. Research in these areas is vigorous and truly international, with three major regions making almost equal contributions: America, Europe and Asia. Asia now has its own top international organic chemistry journal—the Asian Journal of Organic Chemistry (AsianJOC) The AsianJOC is designed to be a top-ranked international research journal and publishes primary research as well as critical secondary information from authors across the world. The journal covers organic chemistry in its entirety. Authors and readers come from academia, the chemical industry, and government laboratories.