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Russian Journal of General Chemistry

, Volume 89, Issue 8, pp 1575–1585 | Cite as

Synthesis and Properties of 4,6-Dimethyl-5-pentyl-2-thioxo-1,2-dihydropyridine-3-carbonitrile and 3-Amino-4,6-dimethyl-5-pentylthieno[2,3-b]pyridines

  • D. S. BuryiEmail author
  • V. V. Dotsenko
  • N. A. Aksenov
  • I. V. Aksenova
  • S. G. Krivokolysko
  • L. V. Dyadyuchenko
Article
  • 9 Downloads

Abstract

The reaction of 3-pentylpentane-2,4-dione with cyanothioacetamide afforded 4,6-dimethyl-5-pentyl-2-thioxo-1,2-dihydropyridine-3-carbonitrile. Alkylation of the latter led to the formation of 2-alkylsulfanyl-4,6-dimethyl-5-pentylpyridine-3-carbonitriles or 3-amino-4,6-dimethyl-5-pentylthieno[2,3-b]pyridines, depending on the alkylating agent and reaction conditions. The structures of the key compounds were proved by 2D NMR spectroscopy and X-ray analysis. Biological activity of the synthesized compounds was evaluated in silico. Some compounds were experimentally found to stimulate growth of sunflower seedlings.

Keywords

cyanothioacetamide Thorpe-Ziegler cyclization thieno[2,3-b]pyridines lipophilicity in silico biological activity 1,3,2λ5-diazaphosphinines 

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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, I.V. Aksenova; project no. 4.1196.2017/4.6, N.A. Aksenov). Biological studies were performed in the framework of state assignment of the Ministry of Science and Higher Education of the Russian Federation (project no. 075-00376-19-00) and research project no. 0686-2019-0013.

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Copyright information

© Pleiades Publishing, Ltd. 2019

Authors and Affiliations

  • D. S. Buryi
    • 1
    Email author
  • V. V. Dotsenko
    • 1
    • 2
    • 3
  • N. A. Aksenov
    • 2
  • I. V. Aksenova
    • 2
  • S. G. Krivokolysko
    • 3
    • 4
  • L. V. Dyadyuchenko
    • 5
  1. 1.Kuban State UniversityKrasnodarRussia
  2. 2.North Caucasus Federal UniversityStavropolRussia
  3. 3.KhimEks LaboratoryVladimir Dahl Lugansk National UniversityLuganskUkraine
  4. 4.St. Luka Lugansk State Medical UniversityLuganskUkraine
  5. 5.All-Russian Research Institute of Biological Plant ProtectionKrasnodarRussia

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