Full Paper

Synthesis, Structure, and Spectral Properties of Bis(pyrrol-2-yl)pyridines

  1. Boris A. Trofimov1,
  2. Alexander M. Vasil'tsov1,
  3. Elena Yu. Schmidt1,
  4. Nadezhda V. Zorina1,
  5. Andrey V. Afonin1,
  6. Al'bina I. Mikhaleva1,
  7. Konstantin B. Petrushenko1,
  8. Igor A. Ushakov1,
  9. Leonid B. Krivdin1,
  10. Vitaly K. Belsky2,
  11. Lyubov I. Bryukvina3

Article first published online: 1 SEP 2005

DOI: 10.1002/ejoc.200500336

Issue

European Journal of Organic Chemistry

European Journal of Organic Chemistry

Volume 2005, Issue 20, pages 4338–4345, October 2005

Additional Information

How to Cite

Trofimov, B. A., Vasil'tsov, A. M., Schmidt, E. Y., Zorina, N. V., Afonin, A. V., Mikhaleva, A. I., Petrushenko, K. B., Ushakov, I. A., Krivdin, L. B., Belsky, V. K. and Bryukvina, L. I. (2005), Synthesis, Structure, and Spectral Properties of Bis(pyrrol-2-yl)pyridines. European Journal of Organic Chemistry, 2005: 4338–4345. doi: 10.1002/ejoc.200500336

Author Information

  1. 1

    A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St, Irkutsk 664033, Russian Federation, Fax: +7-3952-419346

  2. 2

    L. Ya. Karpov Institute of Physical Chemistry, 10, Vorontsovo pole, Moscow, 103064, Russian Federation, Fax: +7-095-9752450

  3. 3

    Irkutsk Branch of Institute of Laser Physics, Siberian Branch of the Russian Academy of Sciences, 130A Lermontov St, Irkutsk 664033, Russian Federation, Fax: +7-3952-512160

Publication History

  1. Issue published online: 10 OCT 2005
  2. Article first published online: 1 SEP 2005
  3. Manuscript Received: 11 MAY 2005

SEARCH

SEARCH BY CITATION

ARTICLE TOOLS

View Full Article with Supporting Information (HTML) Get PDF (180K)

Keywords:

  • Acetylene;
  • Heterocycles;
  • X-ray absorption spectroscopy;
  • UV/Vis spectroscopy;
  • Fluorescence spectroscopy

Graphical Abstract

Thumbnail image of graphical abstract

Abstract

2,6-Bis(pyrrol-2-yl)pyridine (4), 2-(pyrrol-2-yl)-6-[2-(1-vinylpyrrol-2-yl)]pyridine (5), 2,6-bis[2-(1-vinylpyrrol-2-yl)]pyridine (6), 2,6-dimethyl-3,5-bis[2-(1-vinylpyrrol-2-yl)] pyridine (9), 3-acetyl-2,6-dimethyl-5-[2-(1-vinylpyrrol-2-yl)]pyridine (10), and 2,6-dimethyl-3-(pyrrol-2-yl)-5-[2-(1-vinylpyrrol-2-yl)]pyridine (11) have been synthesized from the oximes of the corresponding diacetylpyridines in a one-pot procedure by treatment with acetylene in MOH/DMSO systems (M = Li, K) at 80–140 °C under pressures of 25–30 atm, thus illustrating the applicability and general character of the reaction for synthesis of diverse dipyrrole-pyridine assemblies and their N-vinyl and acetyl derivatives. A stable 4·DMSO complex with bifurcated NH···O···HN bonding has been isolated and its X-ray structure determined. Quantum chemical analysis at the B3LYP/6-311G* level shows that the cis-cis conformation of 4 is most stable, with the cis-trans and trans-trans forms accordingly less favorable by 3.2 and 7.8 kcal mol–1. Activation barriers of cis-cis-to-cis-trans and cis-trans-to-trans-trans dynamics are 8.3 and 9.5 kcal mol–1, respectively, which means that internal rotation of the pyrrole rings in 4 is essentially hindered. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

View Full Article with Supporting Information (HTML) Get PDF (180K)