Synthesis and antimicrobial evaluation of new heterocyclic compounds derived from 2-acetyl-5- methyl-2,4-dihydro-3H-pyrazol-3-one

Document Type : Original Article

Authors

1 Heterocyclic Synthesis Lab., Chemistry Department, Faculty of Science, Ain Shams University, Abbassia, 11566, Cairo, Egypt.

2 Department of Petroleum Application, Egyptian Petroleum Research Institute, Nasr City, Cairo, Egypt.

Abstract

The 2-acetyl-5-methyl-2,4-dihydro-3H-pyrazol-3-one 2 prepared via acetylation of 5-methyl-1H-pyrazol-3-one 1 was
reacted with aromatic aldehydes in 1:1 and 1:3 ratio to give chalcone derivatives 3a-c and the tri-condensed product 6. Chalcone
derivative 3a was condensed with hydrazine hydrate and hydroxylamine hydrochloride to give the corresponding bis pyrazole
4 and the oxime 5 derivatives, respectively. Also, it was reacted with bromine in 1:1 and 1:2 ratio to give the mono 7 and the
dibromo 10 derivatives, respectively. Reaction of the monobromo derivative 7 with hydrazine hydrate and thiourea gave the
pyrazolotriazine 8 and the 2-(thiazol-4-yl)-3-pyrazolone 9 derivatives, respectively. Compound 1 was reacted with chloroacetyl
chloride to give the 2-(2-chloroacetyl)pyrazolone 11 derivative, which on reaction with hydrazine hydrate, urea and thiourea
gave the 2-aminoglycyl pyrazolone 12 and the urea and thiourea derivatives 13a,b. Furthermore, reaction of compound 1 with
formaldehyde/piperidine, benzene sulfonyl chloride and chloroacetyl chloride gave the Mannich product 14, the 2-
phenylsulfonyl pyrazolone 15 and the bis pyrazolone 16. All new compounds were prepared using both conventional and
microwave techniques. Elemental analyses together with spectroscopic data including IR, 1H-NMR in addition to 13C-NMR
and mass spectra submit proofs for the chemical structures for all compounds. Some of the new pyrazolone derivatives showed
antimicrobial activities.

Keywords

Journal of Basic and Environmental Sciences
Volume 9, Issue 1
January 2022
Pages 38-48

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