Abstract
2- Ethoxy-4(3H) quinazolinone 1 was synthesized and allowed to react with various halides, namely: alkyl, benzyl, allyl, acyl, haloacetyl, crotonyl, benzoyl, 2-furoyl and 1-naphthalenesulphonyl halides affording quinazoline and quinazolinone derivatives. The reactions of compound 1 with phosphorus oxychloride, phosphorus pentasulfide, ethyl chloroformate, ethyl chloroacetate, α-bromoglucose tetraacetate, p-acylaminobenzenesulfonyl chloride, acrylonitrile, chalcone and chalcone oxide were also investigated. Depending on the reaction condition and reactant halide, the type of substituent (alkyl, acyl, aroyl, etc.) that will reside on either of the expected positions (3 or 4) on the quinazoline moiety can control the reaction pathway for synthesis of the promising products. The significant role of solvent responsible for determining both the reaction pathway and type of products synthesized was also discussed. Some derivatives were chosen for biological screening test against Gram (-ive) and Gram (+ive) bacteria and two strains of fungi.
Highlights
In recent years there has been an increasing interest in the chemistry of 4(3H)-quinazolinones because of their biological importance
By the solvent free reaction of 2-ethoxy (4H)-3, 1-benzoxazin-4-one with ammonium acetate 2-ethoxy (4H)-3,1-quinazolin-4-one 1 was synthesized to be used as the starting material
The interaction of compound 1 with alkyl halides such as methyl iodide, ethyl iodide, benzyl chloride and ethyl chloroacetate, carried out in dry acetone and anhydrous potassium carbonate gave the corresponding N-substituted quinazolinones 2a-d (Scheme 1), respectively
Summary
In recent years there has been an increasing interest in the chemistry of 4(3H)-quinazolinones because of their biological importance. Many of them show antifungal, antibacterial, anticancer, anti-inflammatory, anticonvulsant, immunotropic, hypolipidemic, antitumor, antiulcer, analgesic, antiproliferative activities and inhibitory effects for thymidylate synthase and poly (ADP-ribose) polymerase (PARP) [1-13]. The 4(3H)-quinazolinones can act as semicyclic amides or iminols, due to the tautomeric phenomenon they have. Their reactions in either form with alkyl or acyl halides are perhaps the most interesting due to the large number of heterocycles that are obtained either directly or through further transformations of the initially formed products
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