Affiliation:
1. St. Petersburg State University 198504 St. Petersburg Russian Federation
2. Institute of Organic Chemistry University of Regensburg D-93053 Regensburg Germany
Abstract
AbstractA 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).
Funder
Russian Science Foundation
Subject
General Chemistry,Catalysis,Organic Chemistry