酸介导间歇和流动环化制备2-杂芳基吲哚-3-酮

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-02-18 DOI:10.1021/acs.orglett.5c0014810.1021/acs.orglett.5c00148

Zeynep Saglam, Shuyu Liu, Yiding Chen, Loïc R. E. Pantaine, Matthew G. Lloyd* and Aaron J. Senior*,

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引用次数: 0

摘要

采用间歇和流动两种方法合成了富氮且具有重要生物学意义的2-杂芳基吲哚-3- 1的分子内环化策略。通过高通量筛选，发现柠檬酸在二甲基甲酰胺/水混合物中促进了间歇条件下的反应，该反应可以耐受取代苯环、喹啉和萘的各种电子和位阻性质。利用实验设计对反应的流动条件进行了重新优化，补充了一些底物的批处理条件，大大缩短了反应时间。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Preparation of 2-Heteroaryl-indolin-3-ones by Acid-Mediated Intramolecular Cyclization in Batch and Flow

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Preparation of 2-Heteroaryl-indolin-3-ones by Acid-Mediated Intramolecular Cyclization in Batch and Flow

An intramolecular cyclization strategy to synthesize nitrogen-rich and biologically important 2-heteroaryl-indolin-3-ones has been developed in both batch and flow. Using high-throughput screening, citric acid in a dimethylformamide/water mixture was found to facilitate the reaction under batch conditions, which can tolerate substituted phenyl rings, quinolines, and naphthalenes with a variety of electronic and steric properties. The reaction was reoptimized for flow conditions using design of experiments, complementing the batch conditions for some substrates with greatly reduced reaction times.

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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.