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Investigation of Some Functionalization Reactions of 4‐Benzoyl‐5‐phenyl‐1‐(4‐methoxyphenyl)‐1 H ‐pyrazole‐3‐carbonyl Chloride and Their Antimicrobial Activity
Author(s) -
Korkusuz Elif,
Yıldırım İsmail,
Albayrak Sevil
Publication year - 2013
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.201200568
Subject(s) - chemistry , pyrazole , benzoyl chloride , acetyl chloride , acylation , antimicrobial , medicinal chemistry , benzaldehyde , chloride , alkyl , organic chemistry , catalysis
The 1 H ‐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‐1 H ‐pyrazole‐3‐carboxamide 4a , b and alkyl 4‐benzoyl‐1‐(4‐methoxyphenyl)‐5‐phenyl‐1 H ‐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‐1 H ‐pyrazoles 9a‐c , 4‐benzoyl‐1‐(4‐methoxyphenyl)‐3‐aroyl‐5‐phenyl‐1 H ‐pyrazoles 10a , b and than from the acylation reactions of 9a‐c were obtained the 3,4‐diaroyl‐1‐(4‐acyloxyphenyl)‐5‐phenyl‐1 H ‐pyrazoles 13a‐d . The structures of all new synthesized compounds were established by NMR experiments such as 1 H, and 13 C, 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.