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六氟异丙醇介导的吲哚C-3烷基化反应及吲哚并[2,3-b]喹啉和相关天然产物的合成

HFIP-mediated C-3-alkylation of indoles and synthesis of indolo[2,3-]quinolines & related natural products.

作者信息

Rashid Auqib, Lone Waseem I, Dogra Preeti, Rashid Showkat, Bhat Bilal A

机构信息

Natural Products & Medicinal Chemistry Division, CSIR-Indian Institute of Integrative Medicine, Sanatnagar, Srinagar 190005, India.

Natural Products & Medicinal Chemistry Division, CSIR-Indian Institute of Integrative Medicine Jammu, Jammu and Kashmir 180001, India.

出版信息

Org Biomol Chem. 2024 May 1;22(17):3502-3509. doi: 10.1039/d4ob00414k.

Abstract

An expeditious metal free C-3 alkylation of indoles and its NIS-mediated deviation to indolo[2,3-]quinolines is reported. This protocol, executed in aqueous HFIP has broad substrate scope and is well inclined towards the ideas of sustainable chemistry. Applications of these strategies in accessing bioactive natural products like vibrindole, norcryptotakeine, neocryptolepine and indenoindolone scaffolds has also been demonstrated.

摘要

报道了一种快速的吲哚无金属C-3烷基化反应及其NIS介导的向吲哚并[2,3-]喹啉的转化。该方案在水性HFIP中进行,具有广泛的底物范围,并且非常符合可持续化学的理念。这些策略在获取生物活性天然产物如振动吲哚、降隐托品碱、新隐品碱和茚并吲哚酮支架方面的应用也得到了证明。

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