A preparative method of synthesis of pyrazolylphenyl(phenoxy)acetic acids

TitleA preparative method of synthesis of pyrazolylphenyl(phenoxy)acetic acids
Publication TypeJournal Article
Year of Publication2016
AuthorsMoskvina, VS, Shilin, SV, Khilya, VP
Abbreviated Key TitleDopov. Nac. akad. nauk Ukr.
Date Published10/2016

A new convenient and accessible method of synthesis of 2-(1H-pyrazol-3-yl)phenols through the heterocyclization of enaminoketone acetophenones with hydrazine hydrate and N-methylhydrazine is developed. The reactivity of obtained compounds is studied. It is demonstrated that the alkylation reactions followed by the hydrolysis result in high yields and are a convenient approach to the synthesis of pyrazolylphenylacetic and (N-methylpyrazolyl-3(or 5)-yl)phenoxyacetic acids.

Keywords2-(1N-pyrazol-3-yl)phenole, acetophenone, N-methyl pyrazol-3(or 5)-yl)phenoxyacetic acid, pyrazol-3(or 5)-yl)phenylacetic acid, pyrazole
  1. Biochemistry of phenolic compounds, Ed. J. Harborn, Moscow: Mir, 1968 (in Russian).
  2. Ma Y.-T., Fan H.-F., Gao Yu-Q., Li H., Zhang A.-L., Gao J.-M. Chem. Biol. Drug Des., 2013, 81, Iss. 4: 545-552. https://doi.org/10.1111/cbdd.12064
  3. Gul H.I., Denizci A.A., Erciyas E. Arzneimittelforsch., 2002, 52, Iss. 10: 773-777.
  4. Solodovnichenko N.M., Zuravlyev N.S., Kovalev V.N. Medicinal plant raw materials, Kharkiv: Publ. NFAU, 2001 (in Ukrainian).
  5. Elguero J., Goya P., Jagerovic N., Silva A. M. S. Targets in heterocyclic systems, Rome: Italian Society of Chemistry, 2002, Vol. 6: 52-98.
  6. Pérez-Fernández R., Goya P., Elguero J. ARKIVOC, 2014, Iss. 2: 233-293.
  7. Biegasiewicz K.F., Gordon J.S., Rodriguez D.A., Priefer R. Tetrahedron. Lett., 2005, 55, No 37: 5210-5212. https://doi.org/10.1016/j.tetlet.2014.07.110