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Synthesis, spectroscopic properties and crystal structure determination of 2-(2-pyridin-4-yl-vinyl)-1H-benzimidazole derivatives

Abstract

Substituted 2-(2-pyridin-4-yl-vinyl)-1H-benzimidazole derivatives 2, 3 and 6 were synthesized. 2-(2-Pyridin-4-yl-vinyl)-1H-benzimidazole 2 and 6-methyl-2-(2-pyridin-4-yl-vinyl)-1H-benzimidazole 3 were prepared by condensation reaction from 3-pyridin-4-yl-acrylic acid and corresponding 1,2-phenylenediamines in polyphosporic acid (PPA). 2,7,11-b-Triaza-benzo[c]fluorene 4 was prepared by photochemical dehydrocyclization reaction of ethanolic solution of 2-(2-pyridin-4-yl-vinyl)-1H-benzimidazole 2. 2-(2-Pyridin-4-yl-vinyl)-3H-benzimidazole-6-carbonitrile 6 was prepared by condensation reaction from 3-pyridin-4-yl-propenal and 4-cyano-1,2-phenylenediamine using p-benzoquinone as oxidants. The structure of novel benzimidazole derivatives has been studied by 1H and 13C NMR, IR, MS, UV/Vis and fluorescence spectroscopy. The structure of 2-(2-pyridin-4-yl-vinyl)-1H-benzimidazole 2 was confirmed by X-ray single crystal structure analysis. The conformation of the molecule is E in regard to substituents position around vinyl double C=C bond. The non-planar molecules are mutually connected via the N–H···N and C–H···N type of intermolecular hydrogen bonds into infinite chains spreading along y axis.

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Acknowledgements

The Ministry of Science and Technology of the Republic of Croatia, Zagreb (grant No. 125-0982464-1356) supported this work. The authors wish to thank to the project 119-1193079-1084 under the framework of the scientific programme “Ligands, complexes, proteins—synthesis and structure—properties relationship” for giving us diffraction time for recording of diffraction data.

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Correspondence to Gordana Pavlović.

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Hranjec, M., Pavlović, G., Marinović, M. et al. Synthesis, spectroscopic properties and crystal structure determination of 2-(2-pyridin-4-yl-vinyl)-1H-benzimidazole derivatives. Struct Chem 19, 353–359 (2008). https://doi.org/10.1007/s11224-008-9291-1

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Keywords

  • 2-(2-Pyridin-4-yl-vinyl)-1H-benzimidazole derivatives
  • Synthesis
  • Photochemical dehydrocyclization
  • Spectroscopic characterization
  • X-ray single crystal structure analysis