RECYCLIZATION OF PYRIMIDINIUM SALTS INTO 1,2,4-TRIAZOLE DERIVATIVES

Authors

  • Г. Г. Данагулян Institute of Organic Chemistry, National Academy of Sciences of the Republic of Armenia, Erevan 375091
  • Г. А. Паносян Molecular Structure Research Center, National Academy of Sciences of the Republic of Armenia, Erevan 375014
  • Л. Г. Саакян Institute of Organic Chemistry, National Academy of Sciences of the Republic of Armenia, Erevan 375091

DOI:

https://doi.org/10.1007/7417

Keywords:

arylhydrazines, pyrimidinium salts, 1, 2, 4-triazole, 2-methylaminonicotinic acid ester, NOESY method, rearrangement, recyclization, NMR spectroscopy

Abstract

The interaction of the iodomethylates of pyrimidinyl-2-acetic  acid derivatives with monosubstituted hydrazines, in addition to the products of a Kost–Sagitullin rearrangement, leads also to N-substituted triazoles. The structure of the triazoles was demonstrated by NOESY NMR experiments. The structure of the reaction products was determined on the basis of the response observed in the spectra between the methyl group protons of the triazole ring and the spatially close proton of the substituent in position 1 and a conclusion was drawn on the direction of the  primary attack of nucleophile in the recyclization process of the pyrimidinium salts into a 1,2,4-triazole.

How to Cite
Danagulyan, G. G.; Panosyan, G. A.; Sahakyan, L. G.  Chem. Heterocycl. Compd. 2007, 43, 996. [Khim. Geterotsikl. Soedin. 2007, 1175.]

For this article in the English edition see DOI 10.1007/s10593-007-0155-1


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Published

2023-02-01

Issue

No. 8 (2007)

Section

Original Papers