SYNTHESIS OF TARGET HETEROCYCLIC COMPOUNDS CONTAINING NITROGEN ATOM WITH EXPECTED BIOLOGICAL ACTIVITY

Abstract

The original work of this thesis can be classified into two parts: 1st part: Benzoxazinone 1 was prepared via a cyclization of 5-bromo-2-hexanamidobenzoic acid in acetic anhydride. Benzoxazinone 1 was treated with 1-napthyl amine, 2-amino thiophenol, o-phenylene diamine, thio semicarbazide, ethanol amine, hydrazine hydrate and formamide, to afford the quinazolinone derivatives 2-8, respectively. Meanwhile, compound 7 was allowed to react with phosphorous pentasulphide, carbon disulphide, phenyl isocyanate, phenyl isothiocyanate, acetic acid, acetic anhydride, benzoyl chloride, ethyl chloroacetate, diethyl malonate and triethyl orthoformate, afforded compounds 9-17, respectively. Treatment of compound 7 with benzoxazinone 1 and phthalic anhydride to form quinazolinone derivatives 18 & 19, respectively. Likewise, condensation of compound 7 with different aldehydes gave products 20a-e. Also, reaction of 7 with arylidine malononitrile gave Schiff’s base 21. The treatment of Schiff’s base with methyl thioglycolate and thiophenol produced products 22 & 23. The reaction of quinazolinone 8 with phosphorus pentasulpide and ethyl chloroacetate yielded the derivatives 24 & 25, respectively. The treatment of 25 with sodium hydroxide, p-nitro aniline and hydrazine hydrate, produced products 26-28, respectively. The reaction of the hydrazide 28 with p-anisaldehyde and phthalic anhydride gave products 29 & 30, respectively. On the other hand, compound 28 was allowed to react with thioglycolic acid, ethyl acetoacetate, acetyl acetone, ethyl cyanoacetate and diethyl malonate to produce compounds 31-35, respectively. Also, hydrazide 28 was treated with carbon disuphide, phenyl isothiocyanate and ethyl chloroformate to afford the derivatives 36-38, respectively. The newly synthesized compounds were characterized by IR, 1HNMR, 13CNMR and Mass spectra.