Synthesis and antimicrobial evaluation of new heterocyclic compounds derived from 2-acetyl-5- methyl-2,4-dihydro-3H-pyrazol-3-one | ||
| Journal of Basic and Environmental Sciences | ||
| Volume 9, Issue 1, January 2022, Pages 38-48 PDF (718.28 K) | ||
| Document Type: Original Article | ||
| DOI: 10.21608/jbes.2022.372063 | ||
| Authors | ||
| K. E. Anwer* 1; H. M. Naguib1; M. E. Hasseb2; G. H. Sayed1 | ||
| 1Heterocyclic Synthesis Lab., Chemistry Department, Faculty of Science, Ain Shams University, Abbassia, 11566, Cairo, Egypt. | ||
| 2Department 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 | ||
| Pyrazolone; microwave; conventional; antibacterial; antifungal | ||
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