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

I. Bitter, Zsolt Török, Viktor Csokai, A. Grün, B. Balázs, Gábor Tóth, György M. Keseru, Zoltán Kovári, M. 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
Publication statusPublished - Aug 2001

Fingerprint

Bearings (structural)
Azoles
Alkylating Agents
X ray crystallography
X Ray Crystallography
Alkylation
Nitrogen
Nuclear magnetic resonance
Atoms
imidazole
benzimidazole
2-methylbenzimidazole

Keywords

  • Alkylations
  • Conformational analysis
  • Cyclizations
  • Nitrogen heterocycles

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis and conformational analysis of dicationic N,N′-bridged bis(benzimidazolium) and bis(imidazolium) macrocycles. / Bitter, I.; Török, Zsolt; Csokai, Viktor; Grün, A.; Balázs, B.; Tóth, Gábor; Keseru, György M.; Kovári, Zoltán; Czugler, M.

In: European Journal of Organic Chemistry, No. 15, 08.2001, p. 2861-2868.

Research output: Contribution to journalArticle

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AU - Grün, A.

AU - Balázs, B.

AU - Tóth, Gábor

AU - Keseru, György M.

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