Synthesis and Antimicrobial Activities of Some Novel Quinoxalinone Derivatives

M M Ali,M A Zahran,M S.A El-Gaby,Y A Ammar,M M.F Ismail

doi:10.3390/50600864

M M Ali, M A Zahran + Show 3 more

Open Access

https://doi.org/10.3390/50600864

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Abstract

Condensation of 4-benzoyl-1,2-phenylenediamine with sodium pyruvate in acetic acid furnished two products which were identified as 6-benzoyl and 7-benzoyl-3-methyl-2(1H)quinoxalinones (1a,b). Fusion of 1a with aromatic aldehydes furnished the styryl derivatives 2a-c. Alkylation of 1a,b with dimethyl sulphate or ethyl chloroacetate produced the N-alkyl derivatives 3a,b and 4a,b. Hydrazinolysis of the ester derivative 4a with hydrazine hydrate afforded the hydrazide derivative 5 which underwent condensation with aldehydes to give the corresponding hydrazone derivatives 6a,b. In addition, chlorination of 1a with thionyl chloride afforded the 2-chloro derivative 7 which was subjected to reaction with sodium azide and n-butylamine to yield the corresponding tetrazolo (8) and n-butylamino (9) derivatives, respectively. The structures of the compounds prepared were confirmed by analytical and spectral data. Also, some of the synthesized compounds were screened for antimicrobial activity.

Highlights

Numerous quinoxaline derivatives are important as antibacterial, antifungal, anticancer, antidepressant and antiinflammatory agents [1,2,3]
From this point of view and in continuation of our interest on the chemistry of quinoxaline [4,5,6,7,8,9], it was of interest to synthesized some quinoxalinone derivatives with the aim of investigating their antimicrobial properties
The second isomer was obtained in 30% yield and identified as 7-benzoyl-3-methyl-2(1H)quinoxalinone 1b (Scheme 1)

Summary

Introduction

Numerous quinoxaline derivatives are important as antibacterial, antifungal, anticancer, antidepressant and antiinflammatory agents [1,2,3]. From this point of view and in continuation of our interest on the chemistry of quinoxaline [4,5,6,7,8,9], it was of interest to synthesized some quinoxalinone derivatives with the aim of investigating their antimicrobial properties

Results and Discussion

H NO N CH3

H N N C4H9-n