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Chemistry of Heterocyclic Compounds

, Volume 54, Issue 10, pp 964–970 | Cite as

Synthesis, structure, and biological activity of 2,6-diazido-4-methylnicotinonitrile derivatives

  • Ludmila V. DyadyuchenkoEmail author
  • Irina G. Dmitrieva
  • Nikolai A. Aksenov
  • Victor V. Dotsenko
Article
  • 57 Downloads

A number of 2,6-diazido-4-methylnicotinonitrile derivatives has been synthesized as prospective novel plant growth regulators. The 2-[(triphenylphosphoranylidene)amino]tetrazolo[1,5-a]pyridine derivative is selectively formed from 2,6-diazido-4-methylnicotinonitrile under the conditions of the Staudinger reaction, from which N-(6-azido-5-cyano-4-methylpyridin-2-yl)acylamides can be obtained by sequential reduction and acylation. The obtained azidopyridines are converted into the corresponding 1,2,3-triazoles when treated with 1,3-dicarbonyl compounds in the presence of Et3N. Field studies showed that some of the synthesized compounds were effective growth regulators of wheat.

Keywords

azidopyridines iminophosphoranes nicotinonitriles 1,2,3-triazoles Dimroth reaction Staudinger reaction growth regulating activity 

Notes

Supplementary material

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • Ludmila V. Dyadyuchenko
    • 1
    Email author
  • Irina G. Dmitrieva
    • 2
  • Nikolai A. Aksenov
    • 3
  • Victor V. Dotsenko
    • 3
    • 4
  1. 1.All-Russian Research Institute of Biological Plant ProtectionKrasnodarRussia
  2. 2.Kuban State Agrarian UniversityKrasnodarRussia
  3. 3.North Caucasus Federal UniversityStavropolRussia
  4. 4.Kuban State UniversityKrasnodarRussia

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