Access to Tetrahydropyrido[1,2-a]indol-6-one Derivatives via NHC-Catalyzed Radical Dearomatization of Indoles

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-08-04 DOI:10.1021/acs.orglett.5c02563

Tianjiao Huang, Chenxia Yu, Tuanjie Li*, Kai Zhang* and Changsheng Yao*,

引用次数: 0

Abstract

Tetrahydropyrido[1,2-a]indol-6-one is a significant motif that is widely present in natural bioactive alkaloids. Herein, a facile and efficient access to the tetrahydropyrido[1,2-a]indol-6-one skeleton via NHC (N-heterocyclic carbene)-catalyzed radical relay dearomatization of indoles has been developed. This protocol exhibits metal-free, mild reaction conditions, a broad substrate scope, high efficiency, and excellent diastereoselectivity (30 examples, up to 89% yield and >20:1 dr).

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nhc催化吲哚自由基脱芳反应制备四氢吡啶[1,2-a]吲哚-6- 1衍生物

四氢吡啶[1,2-a]吲哚-6- 1是广泛存在于天然生物碱中的重要基序。本文提出了一种通过NHC （n -杂环碳）催化的吲哚自由基接力脱芳反应，方便、高效地获得四氢吡啶[1,2-a]吲哚-6- 1骨架的方法。该工艺无金属，反应条件温和，底物范围广，效率高，非对映选择性好（30例，产率高达89%，>20:1 dr）。

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.