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Transition-Metal-Free Synthesis of 2-Substituted Benzo[cd]Indoles via the Reaction of 1-Halo-8-lithionaphthalenes with Nitriles.

Semyon V TsybulinMark V KaplanskiyAlexander S Antonov
Published in: Chemistry (Weinheim an der Bergstrasse, Germany) (2024)
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 NMe 2 groups in positions 5 and 6 (i. e. "proton sponge" moiety).
Keyphrases
  • transition metal
  • molecular docking
  • nk cells
  • magnetic resonance
  • electron transfer
  • high resolution
  • molecular dynamics