Chemistry of Heterocyclic Compounds

, Volume 42, Issue 6, pp 782–787 | Cite as

Intermediates in the transformation of 1,2-dialkylpyrimidinium iodides in the Kost-Sagitullin rearrangement

  • G. G. Danagulyan
  • D. A. Tadevosyan
  • F. S. Kinoyan


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.


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


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  1. 1.
    G. G. Danagulyan, F. S. Kinoyan, and D. A. Tadevosyan, Khim. Geterotsikl. Soedin., 303 (2003).Google Scholar
  2. 2.
    G. G. Danagulyan, L. G. Saakyan, A. R. Katritzky, and S. N. Denisenko, Khim. Geterotsikl. Soedin., 1572 (1999).Google Scholar
  3. 3.
    G. G. Danagulyan, Chemical Sciences Doctoral Dissertation, Yerevan (2000).Google Scholar
  4. 4.
    C. Kashima, A. Katoh, M. Shimizu, and Y. Omote, Heterocycles, 22, 11 (1984).CrossRefGoogle Scholar
  5. 5.
    A. N. Kost, R. S. Sagitullin, and G. G. Danagulyan, Khim. Geterotsikl. Soedin., 1400 (1978).Google Scholar
  6. 6.
    R. S. Sagitullin, A. N. Kost, and G. G. Danagulyan, Tetrahedron Lett., 4135 (1978).Google Scholar
  7. 7.
    G. G. Danagulyan and L. G. Sahakyan, Khim. Geterotsikl. Soedin., 1434 (1999).Google Scholar
  8. 8.
    G. G. Danagulyan and L. G. Saakyan, Khim. Zh. Armenii, 53, 147 (2000).Google Scholar
  9. 9.
    W. J. Hale, J. Am. Chem. Soc., 36, 104 (1914).CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, Inc. 2006

Authors and Affiliations

  • G. G. Danagulyan
    • 1
  • D. A. Tadevosyan
    • 1
  • F. S. Kinoyan
    • 1
  1. 1.Institute of Organic ChemistryNational Academy of Sciences of the Republic of ArmeniaYerevanArmenia

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