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Chemistry of Heterocyclic Compounds

, Volume 54, Issue 12, pp 1139–1144 | Cite as

New spiro derivative of dihydro-1,2,3-triazolo[1,5-a]pyrimidine as a product of multicomponent reaction

  • Eugene S. Gladkov
  • Svetlana M. Sirko
  • Vladimir I. Musatov
  • Svetlana V. Shishkina
  • Irina G. Tkachenko
  • Sergey A. KomykhovEmail author
  • Sergey M. Desenko
Article
  • 15 Downloads

A new spiro derivative of dihydro-1,2,3-triazolo[1,5-a]pyrimidine – 5'-amino-6'-cyano-4'H-spiro[cyclohexane-1,7'-[1,2,3]triazolo[1,5-a]-pyrimidine]-3'-carboxamide – was prepared by three-component reaction of 5-amino-1,2,3-triazole-4-carboxamide with malononitrile and cyclohexanone; the structure of product was established by X-ray analysis. Microwave activation and conventional heating showed the formation of single product and the same direction of heterocyclization. Available literature data concerning similar reactions using 3-amino-1,2,4-triazole or 2-aminobenzimidazole were reinvestigated experimentally with consideration of alternative structures; structures of products were studied by NMR including NOE experiments.

Keywords

1,2,3-triazole derivatives microwave synthesis molecular structure investigation multicomponent reactions reaction mechanism X-ray analysis 

Notes

Supplementary material

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • Eugene S. Gladkov
    • 1
    • 2
  • Svetlana M. Sirko
    • 1
  • Vladimir I. Musatov
    • 1
  • Svetlana V. Shishkina
    • 1
    • 2
  • Irina G. Tkachenko
    • 1
    • 3
  • Sergey A. Komykhov
    • 1
    • 2
    Email author
  • Sergey M. Desenko
    • 1
    • 2
  1. 1.State Scientific Institution “Institute for Single Crystals”, National Academy of Sciences of UkraineKharkivUkraine
  2. 2.V. N. Karazin Kharkiv National UniversityKharkivUkraine
  3. 3.Kharkiv Forensic Science Center, Ministry of Internal Affairs of UkraineKharkivUkraine

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