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Some new 3-[7-methoxy-2H-1-benzopyran-2-one-4-yl]-1-(coumarin-3-yl)prop-2-en-1-ones 5a-d (dicoumarinyl chalcones) were synthesized by Wittig reaction of 3-[(triphenylphosphinyl)acetenyl]coumarins 3a-d and 7-methoxy-4- formylcoumarin 4. These chalcones were then utilized for the synthesis of dicoumarinyl pyrazolines 6a-h and 7a-l under microwave irradiation. All the synthesized compounds 5a-d, 6a-h and 7a-l were characterized by IR, 1H NMR, 13C NMR, mass spectral data and elemental analysis. The compounds were subjected to in vitro antimicrobial screening against a representative panel of bacteria (Bacillus subtilis, Staphylococcus aureus, Escherichia coli, Salmonella typhi) and fungi (Aspergillus niger, Candida albicans).