INTERMEDIATES IN THE TRANSFORMATION OF 1,2-DIALKYLPYRIMIDINIUM IODIDES IN THE KOST-SAGITULLIN REARRANGEMENT

Authors

  • Г. Г. Данагулян 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
  • Ф. С. Киноян Institute of Organic Chemistry, National Academy of Sciences of the Republic of Armenia, 375091 Yerevan

DOI:

https://doi.org/10.1007/7955

Keywords:

alkylamines, 1-alkyl-1, 2-dihydro-2-methylidenepyrimidines, anhydro bases, 1, 2-dialkyl-pyrimidinium iodides, pyridone, pyrimidone, Kost–Sagitullin rearrangement, pseudo bases

Abstract

Intermediate recyclization products were obtained in a study of the Kost–Sagitullin rearrangement of a series of 1,2-dialkylpyrimidinium iodides. The initial attack of the nucleophile leads to the formation of products of the addition of the hydroxyl group, namely, the corresponding pseudo bases. Heating one of these intermediates in ethanol or  in the presence of primary amines  leads to rearrangement to give a pyridone derivative. Upon heating in chloroform,  the pseudo bases readily lose a water molecule and are converted to anhydro bases, namely, derivatives of 1-alkyl-1,2-dihydro-2-methylidenepyrimidine.

How to Cite
Danagulyan, G. G.; Tadevosyan, D. A.; Kinoyan, F. S.  Chem. Heterocycl. Compd. 2006, 42, 782. [Khim. Geterotsikl. Soedin. 2006, 894.]

For this article in the English edition see DOI 10.1007/s10593-006-0161-8

 

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Published

2023-08-15

Issue

No. 6 (2006)

Section

Original Papers