SYNTHESIS OF SOME NOVEL HETEROCYCLIC COMPOUNDS CONTAINING PHTHALAZINE OR 1- OXOPHTHALAZINE MOIETY WITH EXPECTED BIOLOGICAL ACTIVITY
M. A. Hawata, A. H. Abdel-Aleem*, A. A. Assar and E. F. Abd Elmaqsoud
Synthesis of new series of phthalazine derivatives starting from phthalic anhydride 1 with benzene or chlorobenzene in the presence of AlCl3 anhydrous afforded 2(a,b), further cyclisation with hydrazine hydrate afforded 3(a,b), by chlorination with POCl3 in DMF gave 4(a,b), phthalazine derivatives 5,6(a-c) were formed by reaction 4(a,b) with aromatic amines. On the reaction of 3(a,b) with chlorosulphonic acid with excess of thionyl chloride at 0Â°C to afforded 7(a,b) which reacted with hydrazine hydrate afforded 8(a,b), phthlazine sulphonylhydrazone derivatives 9,10(a-d) and 11,12(a-c) were formed by reaction 8(a,b) with aromatic aldehydes or sugar aldehydes. On the reaction 3(a,b) with phenylisocyanate or phenylisothiocyanate in benzene afforded 13,14(a,b), according to Mannich condition 15(a,b) were formed by reaction 3(a,b) with pipredine and formaldehyde solution and one drop HCl were refluxed in ethanol. The structures of the synthesized compounds were confirmed by IR, Mass spectra, 1HNMR and 13C NMR spectral data. The biological activities of synthesized compounds were studied.
Keywords: Phthalic anhydride, phthalazine derivatives, phthlazine sulphonylhydrazone, biological activity.
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