铜催化Chan-Lam反应及顺序氧化Fischer吲哚合成制备吲哚衍生物。

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-06-25 DOI:10.1021/acs.orglett.5c01849

Jia-Yi Gao, Xian-Jun Wei, Si-Yu Chen, Hong-Yan Bi*, Cui Liang, Wei-Min Shi* and Dong-Liang Mo*,

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引用次数: 0

摘要

通过铜催化的Chan-Lam反应[3,3]- n3 -羟基喹唑啉酮与烯基硼酸的重排，以中高收率制备了多种α-喹唑啉-4-氧基酮。更重要的是，α-喹唑啉-4-酰氧基酮可以通过与芳酰肼在空气中发生亲核取代、氧化和[3,3]重排的Fischer吲哚合成过程作为吲哚前体。该反应具有底物范围广、官能团相容性好、重排选择性高等特点，得到的α-喹唑啉-4-羟基酮类化合物可作为高位点标记的吲哚前体。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Copper-Catalyzed Chan–Lam Reaction and Sequential Oxidative Fischer Indole Synthesis to Prepare Indole Derivatives

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Copper-Catalyzed Chan–Lam Reaction and Sequential Oxidative Fischer Indole Synthesis to Prepare Indole Derivatives

A variety of α-quinazolin-4-yloxy ketones were prepared in moderate to excellent yields through a copper-catalyzed Chan–Lam reaction/[3,3]-rearrangement of N3-hydroxyquinazolinones and alkenyl boronic acids. More importantly, α-quinazolin-4-yloxy ketones could serve as indole precursors through the Fischer indole synthesis procedure by reacting with arylhydrazines in air, which involved nucleophilic substitution, oxidation, and [3,3]-rearrangement in a one-pot. The present cascade reaction highlights a broad substrate scope, good functional group compatibility, and high rearrangement selectivity, and the obtained α-quinazolin-4-yloxy ketones served as high site-marked indole precursors.

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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.