Iodine‐Catalyzed Vinylogous Friedel–Crafts Alkylation of Indoles: Facile Access to Versatile β‐(3‐Indolyl)carbonyl Frameworks

IF 4 2区化学 Q2 CHEMISTRY, APPLIED

Advanced Synthesis & Catalysis Pub Date : 2025-07-02 DOI:10.1002/adsc.70009

Tapas Kumar Achar, Johncy Jacob, Manash Pratim Sarmah, Manivannan Muthukumar, Arvind Mathur, Richland Tester

引用次数: 0

Abstract

An efficient and scalable metal‐free protocol is developed for C3‐alkylation of indoles employing alkylidene and arylidene malonates as alkyl surrogates, catalyzed by nontoxic and inexpensive iodine. The developed methodology is operationally simple and provides access to a diverse range of products in high yields, up to 95%. The method is further extended and developed into an one‐pot stepwise synthesis strategy for the synthesis of β‐(3‐indolyl)carboxylic acid derivatives. Via product modifications, pharmaceutically relevant 5,10‐dihydroindeno[1,2‐b]indole (DHII) and carboline‐based core for MK2 inhibitor analogues are synthesized.

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碘催化吲哚的葡萄状Friedel-Crafts烷基化：易于获得多功能β -（3 -吲哚基）羰基框架

本文提出了一种高效、可扩展的无金属方案，用于吲哚的C3 -烷基化反应，采用烷基二烯和丙二酸芳烯二烯作为烷基代物，由无毒、廉价的碘催化。所开发的方法操作简单，可获得多种产品，收率高达95%。该方法进一步扩展并发展为一锅逐步合成策略，用于合成β -（3 -吲哚基）羧酸衍生物。通过产物修饰，合成了具有药学意义的5,10‐二氢茚[1,2‐b]吲哚（DHII）和以卡波林为基础的MK2抑制剂类似物核心。

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

Advanced Synthesis & Catalysis 化学-应用化学

CiteScore

9.40

自引率

7.40%

发文量

447

审稿时长

1.8 months

期刊介绍： Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry. The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.