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吲哚、叔丙炔醇和活化炔烃合成环庚[H]吲哚和呋喃[3,4-]咔唑

Synthesis of Cyclohepta[]indoles and Furo[3,4-]carbazoles from Indoles, Tertiary Propargylic Alcohols, and Activated Alkynes.

机构信息

Department of Chemistry, Institute of Synthesis and Application of Medical Materials, Wannan Medical College, Wuhu, Anhui 241002, People's Republic of China.

Key Laboratory of Anti-inflammatory and Immune Medicine, Ministry of Education, Anhui Medical University, Hefei, Anhui 230032, People's Republic of China.

出版信息

Org Lett. 2023 May 5;25(17):3078-3082. doi: 10.1021/acs.orglett.3c00885. Epub 2023 Apr 21.

Abstract

A robust metal-free and environmentally friendly approach to cyclohepta[]indole and furo[3,4-]carbazole frameworks via a three-component reaction from indoles, tertiary propargylic alcohols, and activated alkynes is described. A probable mechanism was proposed on the basis of the isolation and characterization of a key intermediate of the reaction. A gram-scale reaction and product derivatizations were also performed to demonstrate the practicality of the developed methodology.

摘要

本文描述了一种通过吲哚、叔炔丙醇和活化炔烃的三组分反应来构建环庚[吲哚和呋喃[3,4-]咔唑骨架的稳健、无金属和环保方法。基于反应关键中间体的分离和表征,提出了一种可能的反应机理。还进行了克级反应和产物衍生化实验,以证明所开发方法的实用性。

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