engleski

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)-1Hbenzimidazole 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-ylvinyl)- 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.

2-(2-pyridin-4-yl-vinyl)-1H-benzimidazole

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