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Novel route for the transformation of a pyrimidine ring using hydrazides

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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Authors and Affiliations

  1. Organic Chemistry Institute, Armenian Republic National Academy of Sciences, Yerevan, 375091

    G. G. Danagulyan & D. A. Tadevosyan

  2. Center for the Study of Molecular Structure, Armenian Republic National Academy of Sciences, Yerevan, 375014

    R. A. Tamazyan & G. A. Panosyan

Authors
  1. G. G. Danagulyan
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  2. D. A. Tadevosyan
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  3. R. A. Tamazyan
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  4. G. A. Panosyan
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 262–275, February, 2006.

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Danagulyan, G.G., Tadevosyan, D.A., Tamazyan, R.A. et al. Novel route for the transformation of a pyrimidine ring using hydrazides. Chem Heterocycl Compd 42, 233–245 (2006). https://doi.org/10.1007/s10593-006-0077-3

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  • DOI: https://doi.org/10.1007/s10593-006-0077-3

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