Investigation of Some Functionalization Reactions of 4-Benzoyl-5-phenyl-1-(4-methoxyphenyl)-1H-pyrazole-3-carbonyl Chloride and Their Antimicrobial Activity


Korkusuz E. , YILDIRIM İ., ALBAYRAK S.

JOURNAL OF THE CHINESE CHEMICAL SOCIETY, vol.60, no.5, pp.516-525, 2013 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 60 Issue: 5
  • Publication Date: 2013
  • Doi Number: 10.1002/jccs.201200568
  • Title of Journal : JOURNAL OF THE CHINESE CHEMICAL SOCIETY
  • Page Numbers: pp.516-525

Abstract

The 1H-pyrazole-3-carboxylic acid 1 was converted via reactions of its acid chloride 3 with various asymmetrical disubstituted urea and alcohol derivatives into the corresponding novel 4-benzoyl-N-(N',N'-dialkylcarbamyl)-1-(4-methoxyphenyl)-5-phenyl-1H-pyrazole-3-carboxamide 4a,b and alkyl 4-benzoyl-1-(4-methoxyphenyl)-5-phenyl-1H-pyrazole-3-carboxylate 7a-c, respectively, in good yields (57%78%). Friedel-Crafts reactions of 3 with aromatic compouns for 15 min.-2 h led to the formation of the 4-3-diaroyl-1-(4-hydroxyphenyl)-5-phenyl-1H-pyrazoles 9a-c, 4 -benzoyl-1-(4-methoxyphenyl)-3-aroyl-5-phenyl-1H-pyrazoles 10a,b and than from the acylation reactions of 9a-c were obtained the 3,4-diaroyl-1-(4-acyloxyphenyl)-5-phenyl-1H-pyrazoles 13a-d. The structures of all new synthesized compounds were established by NMR experiments such as H-1, and C-13, as well as 2D COSY and IR spectroscopic data, and elemental analyses. All the compounds were evaluated for their antimicrobial activities (agar diffusion method) against eight bacteria and two yeasts.