Chemistry of Heterocyclic Compounds

, Volume 50, Issue 10, pp 1487–1495 | Cite as

Interaction of 2-(1H-benzimidazol-2-yl)-thieno[2,3-b]pyridin-3-amines with ortho-Formylbenzoic Acids

  • V. K. Vasilin
  • D. Yu. Lukina
  • T. A. Stroganova
  • G. D. KrapivinEmail author

We describe a two-stage synthesis of heptacyclic structures, isoindolo[1',2':2,3]pyrido[3",2":4',5']-thieno[3',2':4,5]pyrimido[1,6-a]benzimidazol-6(10bH)-ones, and intermediates, 5,6-dihydropyrido-[3",2":4',5']thieno[3',2':4,5]pyrimido[1,6-a]benzimidazol-6-yl]benzoic acids, as products from the interaction of 3-amino-2-benzimidazolylthieno[2,3-b]pyridines and ortho-formylbenzoic acids. 5,6-Di-hydropyrido[3",2":4',5']thieno[3',2':4,5]pyrimido[1,6-a]benzimidazol-6-yl]benzoic acids were shown to easily oxidize (aromatize) to the corresponding pyrido[3",2":4',5']thieno[3',2':4,5]pyrimido[1,6-a]-benzimidazol-6-yl]benzoic acids. The molecular and crystal structures of 4-(methoxymethyl)-2-methyl-isoindolo-[1',2':2,3]pyrido[3",2":4',5']thieno[3',2':4,5]pyrimido[1,6-a]benzimidazol-6(10bH)-one and 2-[4-(methoxymethyl)-2-methylpyrido[3",2":4',5']thieno[3',2':4,5]pyrimido[1,6-a]benzimidazol-6-yl]- benzoic acid were studied by X-ray crystallography.


2-(1H-benzimidazol-2-yl)thieno[2,3-b]pyridin-3-amines (5,6-dihydropyrido[3",2":4',5']thieno- [3',2':4,5]pyrimidino[1,6-a]benzimidazol-6-yl)benzoic acids (±)-isoindolo[1',2':2,3]pyrido[3",2":4',5']-thieno[3',2':4,5]pyrimidino[1,6-a]benzimidazol-6(10bH)-ones ortho-formylbenzoic acids (pyrido[3",2":4',5']- thieno[3',2':4,5]pyrimidino[1,6-a]benzimidazol-6-yl)benzoic acids molecular structures X-ray structural analysis 


The authors would like to acknowledge the financial support of this study from Ministry of Education and Science of the Russian Federation (project code 25.15).


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Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  • V. K. Vasilin
    • 1
  • D. Yu. Lukina
    • 1
  • T. A. Stroganova
    • 1
  • G. D. Krapivin
    • 1
    Email author
  1. 1.Kuban State Technological UniversityKrasnodarRussia

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