A DOMINO REACTION OF 3-METHYL-1-[6-METHYL-2-(METHYLSULFANYL)PYRIMIDIN-4-YL]-4-[(PHENYLIMINO)METHYL]-1<i>H</i>-PYRAZOL-5-OL WITH HETEROCYCLIC CH ACIDS

Authors

  • А. В. Еркин Saint Petersburg State Institute of Technology (Technical University)
  • С. М. Рамш Saint Petersburg State Institute of Technology (Technical University)

DOI:

https://doi.org/10.1007/1788

Keywords:

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

Abstract

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.

How to Cite
Erkin, A. V.; Ramsh, S. M. Chem. Heterocycl. Compd. 2014, 50, 1102. [Khim. Geterotsikl. Soedin. 2014, 1196.]

For this article in the English edition see DOI 10.1007/s10593-014-1569-1

Author Biographies

А. В. Еркин, Saint Petersburg State Institute of Technology (Technical University)

Андрей Викторович Еркин

Кафедра химии и технологии синтетических биологически активных веществ, доцент, кандидат химических наук

С. М. Рамш, Saint Petersburg State Institute of Technology (Technical University)

Станислав Михайлович Рамш

Кафедра химической технологии органических красителей и фототропных соединений, заведующий кафедрой, профессор, доктор химических наук

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Published

2014-09-08

Issue

No. 8 (2014)

Section

Original Papers