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

А. В. Еркин, С. М. Рамш
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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


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

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