Synthesis and Characterization of Some Quinazolone Derivatives

Reaction of compound 1 with 2,3,4,6-tetra-O-acetyl--D-glucopyranosyl bromide (ABG) afforded 2.Deplocking of 2 with sodium methoxide gave 1. Alkylation of 1 led to the formation of 3a-c. Fusion of 1 with ethylchloroformate and/or ethyl chloroacetate gave 4a,b. Similarly, boiling of 1 with ethyl chloroacetoacetate gave 5.Refluxing of 1 with diphenyl diazomethane gave 6. Compound 7 reacted with some aromatic aldehydes and triethyland/or triphenyl– phosphite in glacial acetic acid to furnish the amino phosphonates 8a-d. Treatment of 7 with 4-aminobenzoic acid gave 9. Boiling 7 and triethylorthoformate in glacial acetic acid gave 10. Condensation of 7 with 4-benzylidene-2-phenyloxazol-5(4H)-one furnished 11. Reaction of 7 with 4-chlorophenyl isocyanate and/or phenylisothiocyanate in boiling anhydrous pyridine gave 12 and/or 14. Refluxing 7 with chloroacetaldehyde in ethanol yielded15. Fusion of 7 with some sultones afforded the corresponding sultams 18a,b. All the new compounds were tested for theirpotential antibacterial activates and the results indicated that some of them showed activity against different types ofbacteria.