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ABSTRACT:
The condensed reaction of aromatic ketone, 5-Chloro-2-hydroxy-4-methyl-acetophenone with aniline derivatives viz. 2,3-Dimethyl-aniline, 2,4-Dimethyl-aniline, 3,4-Dimethyl-aniline and 2,5-Dimethyl-aniline to yield a ketimines, CJ-1 to CJ-4. These were analyzed by employing the techniques such as thin layer chromatography(TLC) and UV-Vis spectra. After confirming their desired molecular studies, these novel ketimines were studied for their antifungal potential.
KEY WORDS: Ketimines, 5-Chloro-2-hydroxy-4-methyl-acetophenone, D. S. Trap, substituted anilines, TLC and UV-Vis, molar extinction coeficients(εmax) and antifungal potential.
INTRODUCTION:
The azomethines are very important synthetic intermediates. Survey of the past literature [1-2] revealed that the chemistry of multiple bonds has achieved an enormous developments, as these compounds are useful in industrial and biological field via cycloaddition reaction [3] and condensation reactions[4]. From the extensive literature survey it is well known that the organic compounds comprising of the >C=N-, >C=C< and >C=O display the biological activity[5]. The ketone undergo condensation reaction with acetyl acetone[6-7]. Recently, we have reported[8] formation of ketimines from o-Hydroxy-acetophenone and different anilines.
In the present work, the condensation reaction of rare aromatic ketone, 5-Chloro-2-hydroxy-4-methyl-acetophenone with aniline derivatives viz. 2,3-Dimethylaniline, 2,4-Dimethylaniline, 3,4-Dimethylaniline and 2,5-Dimethylaniline each of reacted to give formation of ketimine, as per the Scheme-1. On confirming their desired molecular studies, these ketimines were studied for their antifungal potential against antifungal strains A. Niger(plant fungi) and C. albicans(animal fungi).
EXPERIMENTAL:
Chemicals and Reagent:
The raw materials a rare ketone, 5-Chloro-2-hydroxy-4-methyl-acetophenone with aniline derivatives viz. 2,3Dimethyl-aniline, 2,4-Dimethyl-aniline, 3,4-Dimethylaniline and 2,5-Dimethyl-aniline were of synthesis grade, used for the preparation of ketimine. The solvents absolute alcohol(ethanol), toluene and methanol used during synthesis, TLC and UV-Vis spectra. The reactions were monitored by employing the techniques such as TLC on aluminium plates coated with silica gel 60 F 254 (Merck) and UV-Vis monitored on Shimadzu-1800 spectrophotometer. The antifungal strains A. niger (NCIM-618) and C. albicans(NCIM-3557) were purchased from National Collection of Industrial Microorganisms (NCIM) NCL, Pune.
General Procedure for the Synthesis of Ketimines:
The condensation reaction of aromatic ketone, 5-Chloro-2-hydroxy-4-methyl-acetophenone with aniline derivatives viz. 2,3-Dimethylaniline, 2,4-Dimethylaniline, 3,4-Dimethylaniline and 2,5-Dimethylaniline each of 0.001 mole in toluene on reflux for about 5-6 hrs(clear TLC) using Dean and Stark apparatus, gave formation of ketimines[9-13]. The reaction completion is monitored by employing the techniques such as TLC on aluminium plates coated with silica gel 60 F254....