NOVEL ROUTE FOR THE TRANSFORMATION OF A PYRIMIDINE RING USING HYDRAZIDES

Authors

  • Г. Г. Данагулян Organic Chemistry Institute, Armenian Republic National Academy of Sciences, Yerevan 375091
  • Д. А. Тадевосян Organic Chemistry Institute, Armenian Republic National Academy of Sciences, Yerevan 375091
  • Р. А. Тамазян Center for the Study of Molecular Structure, Armenian Republic National Academy of Sciences, Yerevan 375014
  • Г. А. Паносян Center for the Study of Molecular Structure, Armenian Republic National Academy of Sciences, Yerevan 375014

DOI:

https://doi.org/10.1007/8064

Keywords:

pyrimidinium iodide, pyrazolo[1, 5-a]pyrimidine, Kost–Sagitullin rearrangement, recyclization, X-ray analysis

Abstract

It has been shown from X-ray structural analytical data that the reaction of 2-ethoxycarbonylmethyl-1,4,6-trimethylpyrimidinium iodide with carboxylic acid hydrazides gives pyrazolo[1,5-a]pyrimidine derivatives and not the isomeric triazolo[4,3-a]pyridines previously reported. This novel and previously unreported rearrangement of 1,2-dialkylpyrimidinium salts occurs via recyclization of the pyrimidine ring with inclusion of a fragment of the nucleophilic reagent into the transformation product.

How to Cite
Danagulyan, G. G.; Tadevosyan, D. A.; Tamazyan, R. A.; Panosyan, G. A.  Chem. Heterocycl. Compd. 2006, 42, 233. [Khim. Geterotsikl. Soedin. 2006, 262.]

For this article in the English edition, see DOI 10.1007/s10593-006-0077-3


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Published

2023-09-18

Issue

No. 2 (2006)

Section

Original Papers