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Russian Journal of General Chemistry

, Volume 89, Issue 10, pp 2018–2026 | Cite as

Synthesis and Cyclizations of N-(Thieno[2,3-b]pyridin-3-yl)cyanoacetamides

  • E. A. Chigorina
  • A. V. Bespalov
  • V. V. DotsenkoEmail author
Article
  • 9 Downloads

Abstract

3-Aminothieno[2,3-b]pyridine-2-carboxylic acid esters readily reacted with 3,5-dimethyl-1-(cyanoacetyl)-1H-pyrazole to give previously unknown N-(thieno[2,3-b]pyridin-3-yl)cyanoacetamides. Reactions of the latter with 2-(arylmethylidene)malononitriles were nonselective, and mixtures of different heterocyclization products were generally formed. The cyclization of ethyl 4,6-dimethyl-3-[(cyanoacetyl)amino]thieno[2,3-b]-pyridine-2-carboxylate afforded 2,4-dihydroxy-7,9-dimethylthieno[2,3-b : 4,5-b′]dipyridine-3-carbonitrile whose tautomeric equilibrium was studied by DFT quantum chemical calculations. In silico analysis of biological activity of the synthesized compounds was performed.

Keywords

cyanoacetylation cyanoacetylpyrazole thieno[2,3-b]pyridines Dieckmann cyclization thieno[2,3-b : 4,5-b′]dipyridines 

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Notes

Funding

This study was performed under financial support by the Ministry of Science and Higher Education of the Russian Federation (project no. 4.5547.2017/8.9; V.V. Dotsenko).

Conflict of Interest

No conflict of interest was declared by the authors.

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Copyright information

© Pleiades Publishing, Ltd. 2019

Authors and Affiliations

  • E. A. Chigorina
    • 1
  • A. V. Bespalov
    • 2
  • V. V. Dotsenko
    • 2
    • 3
    Email author
  1. 1.Institute of Chemical Reagents and High Purity Chemical Substances of National Research Centre “Kurchatov Institute,”MoscowRussia
  2. 2.Kuban State UniversityKrasnodarRussia
  3. 3.North-Caucasian Federal UniversityStavropolRussia

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