INVESTIGATION OF THE NUCLEOPHILIC REARRANGEMENT OF 2-(CYANOMETHYL)-1,4,6-TRIMETHYLPYRIMIDINIUM IODIDE INTO 4,6-DIMETHYL-2-METHYLAMINONICOTINIC ACID NITRILE

Authors

  • Г. Г. Данагулян Institute of Organic Chemistry, National Academy of Sciences of the Republic of Armenia, 375091 Yerevan
  • Л. Г. Саакян Institute of Organic Chemistry, National Academy of Sciences of the Republic of Armenia, 375091 Yerevan
  • Д. А. Тадевосян Institute of Organic Chemistry, National Academy of Sciences of the Republic of Armenia, 375091 Yerevan

Keywords:

2-alkylaminonicotinonitrile, pyrimidinium salt, deuterium exchange, Kost–Sagitullin nucleophilic rearrangement

Abstract

2-(Cyanomethyl)-1,4,6-trimethylpyrimidinium iodide is rearranged into 4,6-dimethyl-2-methylamino-nicotinic acid nitrile by interaction with alcoholic solutions of sodium ethylate, methylamine, and also glycine and β-alanine ethyl esters. This conversion was also observed for the first time for pyrimidinium salts during the process of recording 1H NMR spectra in CD3OD solution containing CD3ONa. After the rearrangement deuterium exchange of the protons of the pyridine ring methyl groups was noted spectrally. It was demonstrated experimentally that for carrying out and completing the recyclization a quantity of nucleophilic reagent must convert the molar equivalent quantity of pyridinium salt.

How to Cite
Danagulyan, G. G.; Sahakyan, L. G.; Tadevosyan, D. A. Chem. Heterocycl. Compd. 2004, 40, 465. [Khim. Geterotsikl. Soedin. 2004, 560.]

For this article in the English edition, see DOI 10.1023/B:COHC.0000033539.37576.76

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Published

2004-04-25

Issue

No. 4 (2004)

Section

Original Papers