%0 Journal Article
%T Novel Synthesis and Antimicrobial Evaluation of Some New Cyclic Ketones
%J American Journal of Organic Chemistry
%@ 2163-1301
%D 2013
%I 
%R 10.5923/j.ajoc.20130301.02
%X A series of 5-oxohexannitrile derivatives IIa-d was prepared by reaction of acrylonitrile with ketones Ia-d. On the other hand, semicarbazone derivatives IVa-d were obtained upon reaction of IIa-d with semicarbazide. Hydrolysis and esterification in one step reaction of ¦Ä-ketonitrile IIa-d resulted in the formation of the corresponding ¦Ä-ketoesters Va-d. The ¦Ä-ketoesters Va-d is readily cyclized to the corresponding cyclohexan-1,3-diones VIa-d when heated with alcoholic sodium methoxide. Moreover, coupling of VIa, VIb and VId with aryl diazonium chloride afforded the corresponding 2-(aryl diazenyl) derivatives VIIa-f, respectively. Furthermore, bis-(2,6-diketo-3-phenylcyclohexyl)methane VIII was synthesized by condensing VIa with benzaldehyde. Bromination of VId in dilute acetic acid afforded the corresponding bromo derivative IX. Heating of cyclohexanone-2-methyl propionate in alcoholic sodium methoxide afforded bicycle[1,3,3]nonan-2,9-dione X. These compounds were characterized by analytical and spectral analyses and screened for their antibacterial activity against Gram-possitive bacteria and Gram-negative bacteria. The synthesized compounds (VIIa-f)-X showed significant antibacterial activity against P. Aeruginosa (MIC 0.30-0.45 ¦Ìg/mL), S. Aureus (MIC 0.25-0.45 ¦Ìg/mL) and B. Subtilis (MIC 0.20-0.45 ¦Ìg/mL) and exhibited moderate antibacterial activity against E. Coli (MIC 0.30-0.45 ¦Ìg/mL) compared with the standard drug Ciprofloxacin.
%K Cyclohexan-1
%K 3-Dione
%K Semicarbazone
%K Cyclic Ketones
%K Antimicrobial Activity
%K Minimum Inhibitory Concentration (MIC)
%U http://article.sapub.org/10.5923.j.ajoc.20130301.02.html