Investigation of Some Functionalization Reactions of 4‐Benzoyl‐5‐phenyl‐1‐(4‐methoxyphenyl)‐1H‐pyrazole‐3‐carbonyl Chloride and Their Antimicrobial Activity. Issue 5 (25th February 2013)

• Record Type: Journal Article
• Authors: Korkusuz, Elif; Yıldırım, İsmail; Albayrak, Sevil
• Is Part Of: Journal of the Chinese Chemical Society. Volume 60:Issue 5(2013:May)
• Page Start: 516
• Page End: 524
• Publication Date: 2013-02-25
• Subjects: Chemistry -- Periodicals; Electronic journals; 540.5
• DOI: 10.1002/jccs.201200568
• Languages: English
• ISSNs: 0009-4536

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>The 1<italic>H</italic>‐pyrazole‐3‐carboxylic acid <bold>1</bold> was converted via reactions of its acid chloride <bold>3</bold> with various asymmetrical disubstituted urea and alcohol derivatives into the corresponding novel 4‐benzoyl‐<italic>N</italic>‐(<italic>N′</italic>, <italic>N′</italic>‐dialkylcarbamyl)‐1‐(4‐methoxyphenyl)‐5‐phenyl‐1<italic>H</italic>‐pyrazole‐3‐carboxamide <bold>4a</bold>, <bold>b</bold> and alkyl 4‐benzoyl‐1‐(4‐methoxyphenyl)‐5‐phenyl‐1<italic>H</italic>‐pyrazole‐3‐carboxylate <bold>7a‐c</bold>, respectively, in good yields (57%‐78%). Friedel‐Crafts reactions of <bold>3</bold> with aromatic compouns for 15 min.‐2 h led to the formation of the 4‐3‐diaroyl‐1‐(4‐hydroxyphenyl)‐5‐phenyl‐1<italic>H</italic>‐pyrazoles <bold>9a‐c</bold>, 4‐benzoyl‐1‐(4‐methoxyphenyl)‐3‐aroyl‐5‐phenyl‐1<italic>H</italic>‐pyrazoles <bold>10a</bold>, <bold>b</bold> and than from the acylation reactions of <bold>9a‐c</bold> were obtained the 3, 4‐diaroyl‐1‐(4‐acyloxyphenyl)‐5‐phenyl‐1<italic>H</italic>‐pyrazoles <bold>13a‐d</bold>. The structures of all new synthesized compounds were established by NMR experiments such as ¹H, and ¹³C, 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.</p> </abstract>