Chemistry of Heterocyclic Compounds

, Volume 50, Issue 8, pp 1102–1106 | Cite as

A Domino Reaction of 3-Methyl-1-[6-Methyl-2-(Methylsulfanyl)Pyrimidin-4-yl]-4-[(Phenyl-Imino)Methyl]-1H-Pyrazol-5-ol with Hetero-Cyclic ch Acids


The reaction of 3-methyl-1-[6-methyl-2-(methylsulfanyl)pyrimidin-4-yl]-4-[(phenylimino)methyl]-1H-pyrazol- 5-ol with heterocyclic CH acids is accompanied by a formal cleavage of the substrate and the formation of substituted 1-(pyrimidin-4-yl)pyrazole and aniline. The possibility of isolation of the azomethine (aminomethylеne) derivative of CH acids formed in the process depends on the electrophilicity of its α-carbon atom. In the case of increased electrophilicity, this compound reacts in situ with CH acid to form methylеne bis-СН acids with elimination of aniline.


azomethines enamines CH acids 3-methyl-1-[6-methyl-2-(methylsulfanyl)pyrimidin-4-yl]-4-[(phenylimino)methyl]-1H-pyrazol-5-ol 5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one pyrimidine-2,4,6(1H,3H,5H)-trione AdN-E mechanism electron density partial charge tetrahedral intermediate 


  1. 1.
    G. Varvounis, Y. Fiamegos, and G. Pilidis, Adv. Heterocycl. Chem., 95, 27 (2008).CrossRefGoogle Scholar
  2. 2.
    L. Hennig, M. Alva-Astudillo, G. Mann, and T. Kappe, Monatsh. Chem., 123, 571 (1992).CrossRefGoogle Scholar
  3. 3.
    A. V. Erkin and V. I. Krutikov, Zh. Obsch. Khim., 81, 1360 (2011). [Russ. J. Gen. Chem., 81, 1705 (2011).]Google Scholar
  4. 4.
    S. Hünig, Justus Liebigs Ann. Chem., 574, 106 (1951).CrossRefGoogle Scholar
  5. 5.
    E. Yu. Belyaev and B. V. Gidaspov, Aromatic Nitrosocompounds [in Russian], Khimiya, Leningrad (1989), p. 11.Google Scholar
  6. 6.
    D. Barton and U. D. Ollis (editors), General Organic Chemistry [Russian translation], Vol. 3, Khimiya, Moscow (1982), p. 515.Google Scholar
  7. 7.
    A. Tutalkova and P. Vetešnik, Collect. Czech. Chem. Commun., 37, 656 (1972).CrossRefGoogle Scholar
  8. 8.
    J. March, Advanced Organic Chemistry [Russian translation], Vol. 2, Mir, Moscow (1987), p. 61.Google Scholar
  9. 9.
    F. A. L'Eplattenier, L. Vuitel, H. Junek, and O. S. Wolfbeis, Synthesis, 543 (1976).Google Scholar
  10. 10.
    A. V. Erkin and V. I. Krutikov, Zh. Obsch. Khim., 81, 294 (2011). [Russ. J. Gen. Chem., 81, 392 (2011).]Google Scholar
  11. 11.
    W. Hänsel, Justus Liebigs Ann. Chem., 1680 (1976).Google Scholar

Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  1. 1.Saint Petersburg State Institute of Technology (Technical University)Saint PetersburgRussia

Personalised recommendations