SYNTHESIS OF HETEROCYCLIC COMPOUNDS AND THEIR MICROBIAL ACTIVITY IN CHICK PEA
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Date
2012
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PAU Ludhiana
Abstract
Azo anils were synthesized by conventional and microwave irradiation methods .
The diazonium salts from three amines viz aniline, 4- aminophenazone , 4- nitroaniline was
prepared. Azo compounds were synthesized by reacting different aldehydes namely
benzaldehyde, 2- chloro benzaldehyde , 4- chloro benzaldehyde, 2-methoxy benzaldehyde,
4- methoxy benzaldehyde and 3-nitro benzaldehyde in aqueous sodium hydroxide with
respective diazonium salt at 3o C . These azo compounds were reacted with three amines viz
aniline, 4- aminophenazone and 4- nitroaniline at 30C to obtain the azo anils . All the
compounds synthesized by conventional method were also prepared by using microwave
irradiation method at 360 W . The physical data (colour, state and melting point ) of the
compounds prepared by both the methods was same . However the yield of the
compounds obtained by using microwave method was more as compared to conventional
method. Further the time taken by the microwave method was less as compared to
conventional method. The synthesized azo compounds and azo anils were purified by
recrystallization and then characterized by using the IR and NMR spectroscopic
techniques. Azo anil derivatives were screened for their microbial activity against
Mesorhizobium sp. (LGR 33), Pseudomonas sp. (LK 791) and Bacillus sp. (BSY 101).The
compounds containing pyrazole moiety having no substitution on phenyl ring exhibited no
microbial activity against tested micro-organisms at all the concentrations. Compound (II a)
was effective against Bacillus sp. only at 4000 and 5000 ug/ml concentration. The data
revealed that compounds (VII) and (VIII) were not effective against Bacillus sp at all
concentration. While compound (VII) showed activity against Pseudomonas sp and
compound (VIII) exihibited activity against Mesorhizobium sp. Compounds containing 2-
methoxy (II b) and 4- chloro (II e) groups on phenyl ring were effective against all the
tested microbes . So it was found that all the tested microbes showed mild to moderate
inhibition on growth due to the presence of the more heteroatom in the heterocyclic system
and substitution of chloro, methoxy and nitro on the phenyl ring.
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