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Synthesis and identification of 1,1,3,3-tetra-[1,2-dihydro-1,5-dimethyl-2-phenyl-3-oxopyrazole]propane

https://doi.org/10.21285/2227-2925-2020-10-3-386-392

Abstract

Pyrazole derivatives are of practical value as analytical reagents, dyes and medicinal substances. It is known that 1,2-dihydro-1,5-dimethyl-2-phenylpyrazol-3H-one (antipyrine) and its bidentate derivatives are good analytical reagents for d-metal ions (Cd2+, Fe3+, Sc3+, Ti4+, Zn2+, Co2+, etc.). The chelating ability of bi-, tri- and tetradentate antipyrine derivatives make them promising organic ligands for the synthesis of organometallic coordination polymers. Therefore, synthesis of new tetradentate derivatives of 1,2-dihydro-1,5-dimethyl-2-phenyl-3Hpyrazole-one seems to be a highly relevant research task. The aim of this work was to synthesize and study a new substance – 1,1,3,3-tetra-[1,2-dihydro-1,5-dimethyl-2-phenyl-3-oxopyrazole]propane (tetraantipyryl-propane). A review of existing methods for the synthesis of antipyrine derivatives through condensation of 1,2-dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-one with aliphatic and aromatic aldehydes was carried out. A method was developed for the preparation and purification of 1,1,3,3-tetra-[1,2-dihydro-1,5-dimethyl-2-phenyl-3-oxopyrazole]propane by the reaction of electrophilic substitution of the protonated form of propandial (malonic dialdehyde) in the aromatic ring of the oxopyrazole heterocycle with a yield of 17.1%. The resulting compound is a white crystalline substance, readily soluble in organic polar and non-polar solvents, but insoluble in water. The purity of the recrystallized synthesis product was confirmed by measuring its melting point and conducting a qualitative reaction with sodium nitrite to detect an unsubstituted oxopyrazole cycle in the reaction substrate. The structure of 1,1,3,3-tetra-[1,2-dihydro-1,5-dimethyl-2-phenyl-3-oxopyrazole]propane was established by mass spectrometry and Raman spectroscopy.

About the Authors

D. V. Babadeev
Kazan Federal University
Russian Federation

Dmitrii V. Babadeev, Master Student, Alexander Butlerov Institute of Chemistry 

29/1, Kremlin St., Kazan, 420111



E. A. Stroganova
Orenburg State University
Russian Federation

Elena A. Stroganova, Cand. Sci (Chemistry), Senior Lecturer, Chemistry Department

13, Pobedy Ave., Orenburg, 460018



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Review

For citations:


Babadeev D.V., Stroganova E.A. Synthesis and identification of 1,1,3,3-tetra-[1,2-dihydro-1,5-dimethyl-2-phenyl-3-oxopyrazole]propane. Proceedings of Universities. Applied Chemistry and Biotechnology. 2020;10(3):386-392. (In Russ.) https://doi.org/10.21285/2227-2925-2020-10-3-386-392

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ISSN 2227-2925 (Print)
ISSN 2500-1558 (Online)