Journal of the Serbian Chemical Society 2011 Volume 76, Issue 3, Pages: 329-339
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Design, synthesis and antibacterial activity of new phthalazinedione derivatives
Khalil El-Galil Abd M., Berghot Moged A., Gouda Mostafa A.
Dibenzobarrelene (1) was utilized as the key intermediate for the synthesis
of some new 2-substituted (1,4-dioxo-3,4,4e,5,10,10ahexahydro-
1H-5,10-benzeno-benzo[g]phthalazine: 2, 5a-d, 8a-c and 10. Condensation of 2
with benzaldehyde or anisaldehyde gave the corresponding acrylonitrile
derivative 3a, b, respectively. Thiophene derivatives 4a, b were obtained via
the Gewald reaction of 2 with cyclohexanone or pentanone, respectively.
Treatment of 5d with acetyl chloride or p-toluenesulfonyl chloride afforded
the corresponding esters 6, 7, respectively. Cyclization of 8a-c with
formalin afforded the corresponding triazine derivatives 9a-c. Ring opening
of 10 with sodium hydroxide gave the corresponding triazole derivative 11,
which when alkylated with pentyl bromide afforded the pentylsulfanyl
derivative 12. Representative compounds of the synthesized products were
established and evaluated as antibacterial agents.
Keywords: dibenzobarrelene, phthalazine, thiophene, triazine, triazole, antibacterial agents
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