Triflorometil Grubuna Sahip Pirazol-3-karboksilik Asit Sentezi ve Bazı Tepkimeleri

Authors : Elif HACIALİOĞLU, Volkan TAŞDEMİR, Hasan GENÇ, İsrafil TOZLU

Pages : 645-654

Doi:10.17714/gumusfenbil.528165

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Publication Date : 2019-10-15

Article Type : Research Paper

Abstract :4-benzoyl-5-phenyl-1-(4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carboxylic acid 2 was obtained from 4-benzoyl-5-phenyl-2,3-furandione 1 and (4-(trifluoromethyl)phenyl) benzaldehyde-phenyl hydrazone 1a . Obtained new pyrazole carboxylic acid derivative was converted into acid chloride form. Reaction of new derivatives between acid chloride and some of nucleophiles were progressed. The esters ( 4a-c ) were obtained using Schotten Baumann method with the corresponding alcohols and acid chloride ( 3 ). Pyrazolopiridazinone derivatives ( 8 , 9 , 10 ) were obtained as a result of cyclization reactions between pyrazole carboxylic acid and various hydrazines. Additionally, reactions between an acide chloride 3 and certain amines and ureas were carried out to yield amides ( 5a , 5b-f ) and carbo-urea ( 6a-c ) derivatives. The nitrile compound ( 7 ) was also synthesized from the amine compound via the removal of water with the use of SOCl 2 and DMF. All synthesized molecules were subjected to antibacterial activity to see their potential as unknown reagent. 6-nitro-3,4-diphenyl-2-(4-(trifluoromethyl)phenyl)-2,6-dihydro-7H-pyrazolo[3,4-d]pyridazin-7-one ( 10) showed antibacterial activity against only the Gram-positive bacteria, Bacillus cereus and Micrococcus luteus, with a MIC value of 32 and 128 µg/mL, respectively. This finding revealed that functional group is important for antibacterial activity. Compound 10 having a nitro group inhibited growing of bacteria more than positive control, streptomycin in two different types of bacteria. This might be a good clue for further investigation about antibacterial agents.
Keywords : Cyclic oxalyl compounds, Cyclization, Fluoride, Pyrazole