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2-aryl(hetaryl)-4H-[1,2,4]triazolo[1,5-a]benzimidazoles

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Abstract

2-(4-Methylphenyl)-4H-[1,2,4]triazolo[1,5-a]benzimidazole and its previously unknown 2-(2-furyl)- and 2-(2-thienyl)-substituted analogs were synthesized by cyclization of benzimidazole-1,2-diamine with the corresponding carboxylic acid chlorides. The IR, 1H, 13C, and 15N NMR, and mass spectra of the cyclization products in combination with the results of quantum-chemical calculations of NMR chemical shifts showed radical differences of [1,2,4]triazolo[1,5-a]benzimidazoles having no substituent on N4 from the recently reported low-melting products of oxidation of 2-amino-1-arylmethylideneaminobenzimidazoles with (diacetoxy-λ3-iodanyl)benzene, which, as we believe, were erroneously assigned analogous structure.

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Authors and Affiliations

  1. Research Institute of Physical and Organic Chemistry, Southern Federal University, pr. Stachki 194/2, Rostov-on-Don, 344090, Russia

    A. S. Morkovnik, T. A. Kuz’menko, L. N. Divaeva & G. S. Borodkin

Authors
  1. A. S. Morkovnik
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  2. T. A. Kuz’menko
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  3. L. N. Divaeva
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  4. G. S. Borodkin
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Correspondence to A. S. Morkovnik.

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Original Russian Text © A.S. Morkovnik, T.A. Kuz’menko, L.N. Divaeva, G.S. Borodkin, 2013, published in Zhurnal Organicheskoi Khimii, 2013, Vol. 49, No. 6, pp. 909–917.

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Morkovnik, A.S., Kuz’menko, T.A., Divaeva, L.N. et al. 2-aryl(hetaryl)-4H-[1,2,4]triazolo[1,5-a]benzimidazoles. Russ J Org Chem 49, 895–903 (2013). https://doi.org/10.1134/S107042801306016X

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  • DOI: https://doi.org/10.1134/S107042801306016X

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