Cover Feature: Transition-Metal-Free Synthesis of 2-Substituted Benzo[cd]Indoles via the Reaction of 1-Halo-8-lithionaphthalenes with Nitriles (Chem. Eur. J. 10/2024)

被引：0

作者：

Tsybulin, Semyon V. ^{[1
]}

Kaplanskiy, Mark V. ^{[1
]}

Antonov, Alexander S. ^{[2
]}

机构：

[1] St Petersburg State Univ, St Petersburg 198504, Russia

[2] Univ Regensburg, Inst Organ Chem, D-93053 Regensburg, Germany

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2024年 / 30卷 / 10期

基金：

俄罗斯科学基金会;

关键词：

heterocycles; indoles; naphthalene; nucleophilic substitution; organolithiums;

D O I：

10.1002/chem.202400309

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A simple and effective organolithium approach to the synthesis of 2-substituted benzo[cd]indoles from peri-dihalonaphthalenes and nitriles has been developed. The reaction proceeds via a surprisingly easy intramolecular aromatic nucleophilic substitution facilitated by the “clothespin effect”. The discovered transformation provides good isolated yields, allows usage of an extensive range of nitriles, and demonstrates a good substituents tolerance. UV-absorption and NMR spectra of the obtained benzo[cd]indoles and their protonated forms demonstrated exclusive protonation to the indole nitrogen atom even in the presence of two NMe2 groups in positions 5 and 6 (i. e. “proton sponge” moiety). © 2024 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.

引用

页数：1