Synthetic Approaches and Biological Evaluation of Some New Sulfonate Ester-Containing Imidazolone Derivatives

Abstract

Oxazolone derivative 2 was utilised as a key intermediate for the synthesis of some new imidazolone deriva- tives. Reaction of 2 with p-aminoacetophenone in the presence of acetic acid containing catalytic amount of freshly fused sodium acetate gives the corresponding imidazolone derivative 3 which on reaction with diethyl oxalate in the presence of granulated sodium metal afforded the corresponding imidazolone derivative 4. Condensation of compound 3 with some aromatic aldehydes afforded the corresponding cinnamoylphenyl derivatives 5a-c, respectively. Besides, compounds 5a-c reacted with hydrazine hydrate in boiling ethanol and yield the corresponding 4-arylidene-1- (p-(5-aryl-2- pyrazolin-3-y1) phenyl)-2-phenyl-2-imidazolin-5-ones 6a-c, respectively. Moreover, refluxing of compounds 5a-c with both ethylcyanoace- tate and/or malononitrile in ethanol and ammonium acetate afforded 7a-c and 8a-c, respectively. Claisen reaction of 3 with ethylacetate gives the corresponding imidazolone derivative 9 which on reaction with thiourea in ethanol afforded the cor- responding thienopyrimidine derivative 10. On the other hand, reaction of oxazolone 2 with both ethyl p-aminobenzoate and anthranilic acid in glacial acetic acid and freshly fused sodium acetate has been also studied. Structures of the newly synthesized compounds were established by elemental analysis and spectral data. Representative compounds of the synthe- sized products were tested and evaluated as antifungal and antimicrobial agents. Most of compounds exhibited good activi- ties, where 3, 5b, 5c, 6a, 7b, 7c, 8a, 9, 11, 13 and 14 exhibited good activities against Bacillus Thuringenesis and Klebseilla Pneumonia, while compounds 3, 4, 6a, 6b, 6c, 7c, 8a, 8c, 11, 12 and 16 exhibited good activities against Trichoderma