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

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

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

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

引用次数: 0

Abstract

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.