J. Chem. En. Sci. A.

One-Pot Synthesis of Schiff Base Compounds Derived From 2-Nitro Benzoic Acid With Aldehydes

A.V.G.S. Prasad and P. Venkateswara Rao

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  • DOI Number
    https://doi.org/10.15415/jce.2014.11001 
KEYWORDS

Schiff bases, 2-nitro benzoic acid, Antibacterial activity and Antifungal activity.

PUBLISHED DATE September 2014
PUBLISHER The Author(s) 2014. This article is published with open access at www.chitkara.edu.in/publications
ABSTRACT

In the present study an intermolecular reductive Schiff base formation from nitroarenes and benzaldehydes to yield diarylimines is carried out in the presence of iron powder and dilute acid This type of excellent method avoids use of hazardous solvents, longer reaction time and tedious work up procedure. Advantage of this efficient method is excellent yield of products in crystalline form, short reaction time, simplicity of work up procedure and no use of any type of hazardous solvents. Simply this reaction is economically attractive method for synthesis of Schiff base compounds. All these Schiff base compounds were characterized by means of IR, 1HNMR analysis data. The Schiff base ligands have also been tested in vitro for their antibacterial and anti fungal activity. The experimental results suggest that Schiff base ligands are more potent in anti bacterial and anti fungal activities.

INTRODUCTION

One of the main objectives of organic and medicinal chemistry is the design, synthesis and production of molecules having value as human therapeutic agents.Nitrogen containing compounds are very widely distributed in nature and are essential to life, they play a vital role in the metabolism of all living cells.

At present, greater than 75% drugs and drug candidates incorporate amine functionality. The synthesis of these nitrogen-containing compounds by the easily available imine (Schiff base) is one of the most important and convenient routes

The synthesis and structure assignment by Schiff in 1864 of the first imines was an important event at the beginning of the modern age of chemistry. Schiff’s base compounds and their complexes have significant importance in chemistry. Every year number of reports is published on preparation of these compounds and their application in chemical reactions.However, the enormous potential of Schiff bases is far from exhausted and provides an endless opportunity for chemical creativity.

Schiff bases are important intermediates for the synthesis of various bioactive compounds. Schiff bases are known to have useful biological activity like insecticidal (Jarrahpour et al., 2006), antibacterial (Taggi and Hafez et al., 2002), antituberculosis (Shekarriz and Taslimi, 2004), antimicrobial (Ren et.al., 2002) and anticonvulsant (Hu et al., 2010) activities.

Many derivatives of Schiff bases have found applications in diverse physiological and coordination chemistry area, due promising antibacterial and antivirus activities as well as metal chelating effect and other pharmacological effects (Sandip and Anunay, 2006; Sinha and Tiwari et al., 2008; Sarah and Kelsey et al., 2005).

The present aim of the work is to synthesize a Schiff base derived from 2-nitro benzoic acid with different aldehydes and to characterize them and study their antibacterial activities. Schiff base formation and mechanism

Page(s) 7-14
URL http://dspace.chitkara.edu.in/jspui/bitstream/1/514/3/11001_JCE_Prasad.pdf
ISSN Print : 2349-7564, Online : 2349-7769
DOI https://doi.org/10.15415/jce.2014.11001 
CONCLUSION

Diarylimine have been prepared by a simple and environmentally friendly reductive imination procedure. This methodology uses only Fe(0) in acidic EtOH/H2O as a reductant for nitroarenes, which upon reduction spontaneously condense with an aldehyde in situ.

Above Schiff base compounds shows inherent new generation of series of pharmaceutically important compounds. Conclusively, a variety of Schiff bases derivatives with 2-nitro benzoic acid have been successfully synthesized in appreciable yields and screened in vitro for their antimicrobial activities against Gram-negative bacteria E.Coli.

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