Molecules (Nov 2022)

First Synthesis of 3-Glycopyranosyl-1,2,4-Triazines and Some Cycloadditions Thereof

  • Éva Bokor,
  • Attila Ferenczi,
  • Mahir Hashimov,
  • Éva Juhász-Tóth,
  • Zsófia Götz,
  • Alshimaa Ibrahim Zaki,
  • László Somsák

DOI
https://doi.org/10.3390/molecules27227801
Journal volume & issue
Vol. 27, no. 22
p. 7801

Abstract

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C-glycopyranosyl derivatives of six-membered heterocycles are scarcely represented in the chemical literature and the title 3-glycopyranosyl-1,2,4-triazines are completely unknown. In this paper, the first synthesis of this compound class is accomplished by the cyclocondensation of C-glycosyl formamidrazones and 1,2-dicarbonyl derivatives. In addition, the synthesis of C-glycopyranosyl 1,2,4-triazin-5(4H)-ones was also carried out by the transformation of the above formamidrazones with α-keto-carboxylic esters. Inverse electron demand Diels–Alder reactions of 3-glycopyranosyl-1,2,4-triazines with a bicyclononyne derivative yielded the corresponding annulated 2-glycopyranosyl pyridines.

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