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Abstract <p>The recyclization of 2-(ethoxycarbonyl)methyl-1,4,6-trimethylpyrimidin-1-ium iodide under the action of ethylhydrazine and (4,6-dimethylpyrimidin-2-yl)acetic acid hydrazide, 1-ethyl-3-(ethoxycarbonyl)methyl-5-methyl-1,2,4-triazole and 5,7-dimethyl-3-(ethoxycarbonyl)-2-(4',6'-dimethylyrimidin- 2'-yl-)methylpyrazolo[1,5-<i>a</i>]pyrimidine were synthesized, respectively. Alkylation of 1-ethyl-3-ethoxycarbonylmethyl-5-methyl-1,2,4-triazole with various alkyl iodides yielded the corresponding <i>N</i>-alkyltriazolium salts, and reactions of triazolylacetic acid esters yielded their hydrazides. Based on the nuclear Overhauser effect (NOE), it was clearly demonstrated that alkylation occurs at the N-4 nitrogen atom of the triazole ring.</p>

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Recyclization of a Pyrimidinium Salt as a Synthetic Approach to Novel Nitrogenous Heterocycles

  • 期刊论文

  • 发表日期：

    2025年5月1日

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  • G. G. Danagulyan,
  • L. S. Khachatryan,
  • А. G. Danagulyan,
  • M. Yu. Dangyan,
  • G. A. Panosyan

摘要

Abstract

The recyclization of 2-(ethoxycarbonyl)methyl-1,4,6-trimethylpyrimidin-1-ium iodide under the action of ethylhydrazine and (4,6-dimethylpyrimidin-2-yl)acetic acid hydrazide, 1-ethyl-3-(ethoxycarbonyl)methyl-5-methyl-1,2,4-triazole and 5,7-dimethyl-3-(ethoxycarbonyl)-2-(4',6'-dimethylyrimidin- 2'-yl-)methylpyrazolo[1,5-a]pyrimidine were synthesized, respectively. Alkylation of 1-ethyl-3-ethoxycarbonylmethyl-5-methyl-1,2,4-triazole with various alkyl iodides yielded the corresponding N-alkyltriazolium salts, and reactions of triazolylacetic acid esters yielded their hydrazides. Based on the nuclear Overhauser effect (NOE), it was clearly demonstrated that alkylation occurs at the N-4 nitrogen atom of the triazole ring.