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Vol. 2 No. 4 (2011): October-December 2011

New 4-(substituted)-pyrazolone. Part 1: Microwave-assisted synthesis and antibacterial activity of novel 4-substituted azetidinone derivatives of pyrazolone

Submitted
December 20, 2024
Published
2010-11-15

Abstract

In the present research work, the main motto was to develop novel chemical entities of pyrazolone. The starting material 3-methyl-1-(2,4-dinitrophenyl)-1H-pyrazol-5(4H)-one (1) was synthesized in high yields according to reported method using by the treatment of ethyl aetoacetate with appropriate 1-(2,4-dinitro) phenylhydrazine. Ethyl 2-(4,5-dihydro-3-methyl-1-(2,4-dinitrophenyl)-5-oxo-1H-pyrazol-4-yl)acetate (2) was synthesized by reaction of ethyl chloroacetate with (1). 2-(4,5-dihydro-3-methyl-1-(2,4-dinitrophenyl)-5-oxo-1H-pyrazol-4-yl)acetohydrazide (3) prepared by reaction of hydrazine hydrate with (2) in presence of solvent methanol. The microwave assisted reaction of (3) with different substituted aldehyde in presence of ethanol gives formation of N-(substituted benzylidenyl)-[2-(4,5-dihydro-3-methyl-5-oxo-1-(2,4-dinitrophenyl)-1H-pyrazol-4-yl)acetohydrazide] (4a-4e). The microwave assisted reaction of (4a-4e) with chloroacetyl chloride and triethylamine in presence of DMF as solvent gives formation of 2-(4,5-dihydro-3-methyl-5-oxo-1-(2,4-dinitrophenyl)-1H-pyrazol-4-yl)-acetamide-(3-chloro-4-substituted phenylazetidin-2-one) (RSa-RSe). The products, characterized on the basis of spectral data, have shown moderate to good antibacterial activity against bacteria. The newly synthesized compounds were screened for antibacterial activity.

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