Springer Nature is making SARS-CoV-2 and COVID-19 research free. View research | View latest news | Sign up for updates

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


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.

This is a preview of subscription content, log in to check access.

Scheme 1
Fig. 1
Scheme 2
Fig. 2
Fig. 3
Fig. 4
Fig. 5


  1. 1.

    Lobato J, Canizares P, Rodrigo MA, Linares JJ, Manjavacas G (2006) J Memb Sci 280:351

  2. 2.

    Rodembusch FS, Paulus Leusin F, Bordignon LB, Gallas MR, Stefani VJ (2005) Photochem Photobiol A: Chem 173: 81

  3. 3.

    Costela A, García-Moreno I, Mallavia R, Amat-Guerri F, Barroso J, Sastre R (1998) Opt Commun 152:89

  4. 4.

    Zhou LL, Sun H, Zhang XH, Wu SK (2005) Spectrochim Acta A Mol Biomol Spectrosc 61:61

  5. 5.

    He Y, Yang J, Baogen W., Risen L, Swayze EE (2004) Bioorg Med Chem Lett 14:1217

  6. 6.

    Göker H, Ozden S, Yıldız S, Boykin DW (2005) Eur J Med Chem 40:1062

  7. 7.

    Raymond A Ng., Guan J, Alford VC, Lanter JC, Allan GF, Sbriscia T, Linton O, Lundeen LS, Sui Z (2007) Bioorg Med Chem Lett 17:784

  8. 8.

    Ismail MA, Brun R, Wenzler T, Tanious FA, Wilson WD, Boykin DW (2004) Bioorg Med Chem 12:5405

  9. 9.

    Demirayak S, Abu Mohsen U, Cagri Karaburun A (2002) Eur J Med Chem 37:255

  10. 10.

    Hranjec M, Kralj M, Piantanida I, Sedić M, Šuman L, Pavelić K, Karminski-Zamola G (2007) J Med Chem 50:5696

  11. 11.

    Vivas-Mejía P, Rodríguez-Cabán JL, Díaz-Velázquez M, Hernández-Pérez MG, Cox O, Gonzalez F (1997) Mol Cell Biochem 177:69

  12. 12.

    Yu H, Kawanishi H, Koshima H (2003) Heterocycles 60:1457

  13. 13.

    Alcade E, Dinarés I, Pérez-Garcia L, Roca T (1992) Synthesis 395

  14. 14.

    Alcade E, Dinarés I, Pons JM, Roca TJ (1994) Org Chem 59:639

  15. 15.

    Alcade E, Pérez-Garcia L, Frigola J (1993) Chem Pharm Bull 41:614

  16. 16.

    Hranjec M, Grdiša M, Pavelić K, Boykin DW, Karminski-Zamola G (2003) Il Farmaco 58:1319

  17. 17.

    Starčević K, Boykin DW, Karminski-Zamola G (2002) Heterocyclic Comm 8:221

  18. 18.

    Hranjec M, Starčević K, Zamola B, Mutak S, Đerek M, Karminski-Zamola G (2002) J Antibiotics 55:308

  19. 19.

    Starčević K, Kralj M, Piantanida I, Šuman L, Pavelić K, Karminski-Zamola G (2006) Eur J Med Chem 41:925

  20. 20.

    Hranjec M, Kralj M, Pavelić K, Karminski-Zamola G Hrvatski Patentni glasnik, Patent Appl. HP 20050806A

  21. 21.

    Oxford Diffraction (2004). Oxford Diffraction Ltd., Xcalibur CCD system, CrysAlis Software system, Version 171.23

  22. 22.

    Sheldrick GM (2008) Acta Crystallogr A 64:112

  23. 23.

    Spek AL (1990) Acta Crystallogr A 46:34

  24. 24.

    Fairley TA, Tidwell RR, Donkor I, Naiman NA, Ohemeng KA, Lombardy RJ, Bentley JA, Cory MJ (1993) Med Chem 36:1746

  25. 25.

    Carey JG (1970) GB 1198221 (Cl. C 07d)

Download references


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.

Author information

Correspondence to Gordana Pavlović.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

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).

Download citation


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