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

  • A. V. Erkin
  • S. M. Ramsh

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 


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© Springer Science+Business Media New York 2014

Authors and Affiliations

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

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