alpha-Oxy/thio substituted-beta-keto esters were synthesized through an efficient cross-Claisen condensation of aryl oxy/thio acetic acid ethyl esters with acid chlorides, then it is converted in situ into 4-oxy/thio substituted-1H-pyrazol-5(4H)-ones by the addition of hydrazine or hydrazine derivatives and screened for their antibacterial, antifungal activities.