A stepwise synthetic approach and antibacterial assessment of some new pyrazoline derivatives containing azo and benzyloxy moieties

Daryan O. Ali; Farouq E. Hawaiz

doi:10.21271/ZJPAS.35.1.17

Authors

Daryan O. Ali Department of chemistry, College of Science, University of Sulaymania, Sulaymania-Kurdistan, Iraq
Farouq E. Hawaiz Department of Chemistry, College of Education, University of Salahaddin-Hawler, Erbil 44001, Kurdistan Region, Iraq.

DOI:

https://doi.org/10.21271/ZJPAS.35.1.17

Keywords:

diazotization,, benzylation, chalcones,, , pyrazoline,, antibacterial.

Abstract

This study has designed an efficient stepwise reaction to produce some new pyrazoline derivatives bearing azo and benzyloxy linkages. The reaction was initiated by diazotizing p-aminocetophenone with 2,6-dichlorophenol to give azo compound (1), which was further reacted with benzyl bromide producing the efficacious core material azo-benzyloxy acetophenone(2).

This study has designed an efficient stepwise synthesis to produce some new pyrazoline derivatives that contains azo and benzyloxy linkages. The Synthesis route was initiated by diazotizing p-aminocetophenone with 2,6-dichlorophenol to give azo compound (1), which was then reacted with benzyl bromide producing the efficacious core material azo-benzyloxy acetophenone (2). Moreover, compound (2) was treated with a series of substituted benzaldehydes to form intermediate chalcone derivatives (3a-j) which were then treated with phenylhydrazine via Michael type addition reaction to form azo-benzyloxy pyrazoline molecules (4a-j). Ultimately, the structures of the synthesized compounds were revealed using spectroscopic techniques: FT-IR, ¹H-NMR, ¹³C-NMR, and ¹³C-DEPT-135 spectra. Antimicrobial activities were screened for synthezied Azo-chalcones and Pyrazolines against S.aureus as gram-positive and E.Coli as gram-negative in comparison to a standard antibiotic drug Azithromycine

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