Late-Stage N-Alkenylative Modifications of Indolic Scaffolds with Propiolates: Toward Bisconjugation and Macrocyclization

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-05-14 DOI:10.1021/acs.orglett.5c0116210.1021/acs.orglett.5c01162

Xiaoye Chen, Chi-Ming Au, Pengyuan Fang, Yunsheng Xue*, Ken Cham-Fai Leung* and Wai-Lun Chan*,

引用次数: 0

Abstract

A facile, mild, and scalable late-stage N-alkenylative modification strategy is introduced on 1H-indoles, 9H-carbazoles, and their structural derivatives and analogues, including alkaloids, bioactive agents, and tryptophan motifs, via chemo- and regioselective phosphine-mediated propiolate hydroamination. Saliently, through this protocol, bisconjugation and macrocyclization on (bis)indolic scaffolds can also be accomplished, with the installation of new α,β-unsaturated ester handles for potential further versatile synthetic manipulations.

查看原文本刊更多论文

吲哚支架的后期n -烯基化修饰：向双偶联和大环化方向发展

通过化学和区域选择性膦介导的丙酸氢胺化，对1h -吲哚、9h -咔唑及其结构衍生物和类似物（包括生物碱、生物活性剂和色氨酸基序）进行了简单、温和和可扩展的后期n -烯基化修饰策略。值得注意的是，通过该方案，还可以在（双）吲哚支架上完成双偶联和大环化，并安装新的α，β-不饱和酯手柄，以实现潜在的进一步通用合成操作。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文求助全文

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.