The electron deficient precursor 3 was synthesized by condensation of acetyl derivative 2 with 3-formylchromone (1). Compound 3 reacted with a range of binucleophilic reagents in order to build a variety of heterocyclic systems and explore the reactivity of different electron-deficient sites. Reaction of compound 3 with phenylhydrazine afforded dipyrazole derivative through reaction with both γ-pyrone moieties. Similarly, a variety of dipyrimidines were synthesized by reacting precursor 3 with some 1,3-N,N-binucleophiles. Further, a range of seven-heterocyclic systems, including dibenzodiazepine, dibenzoxazepine and dibenzothiazepine were generated from treating compound 3 with a variety of 1,4-binucleophiles, including o-phenylenediamine, o-aminophenol and o-aminothiophenol, respectively. Reaction of substrate 3 with two carbon nucleophiles namely cyanoacetamide and ethyl cyanoacetate furnished dipyridine 12 and dipyran 13, respectively. The synthesized compounds' antimicrobial efficacy demonstrated a noteworthy inhibitory effect on the growth of microorganisms under investigation. Spectral and analytical data of the synthesized compounds were used to confirm their structures.