Synthesis and conformational analysis of dicationic N,N′-bridged bis(benzimidazolium) and bis(imidazolium) macrocycles

István Bitter, Zsolt Török, Viktor Csokai, Alajos Grün, Barbara Balázs, Gábor Tóth, György M. Keseru, Zoltán Kovári, Mátyás Czugler

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

Two-step alkylations of benzimidazole, 2-methylbenzimidazole, and imidazole at their nitrogen atoms with various bifunctional alkylating agents have afforded a series of 16-membered quaternary azacyclophanes. Of these macrocycles, those bearing methyl or methoxy groups on the azole or at the aromatic bridges have been found to exist as mixtures of conformers. In some cases, the structures of the conformers have been determined by NMR methods and X-ray crystallography, and have been correlated with the results of a computer-aided conformational search.

Original languageEnglish
Pages (from-to)2861-2868
Number of pages8
JournalEuropean Journal of Organic Chemistry
Issue number15
DOIs
Publication statusPublished - Aug 2001

Keywords

  • Alkylations
  • Conformational analysis
  • Cyclizations
  • Nitrogen heterocycles

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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