New compounds were synthesized by the reaction of 3-acetyl-5-methoxy-2-methylbenzofuran (1) with cyanoacetylhydrazine which afforded the hydrazide hydrazone derivative 2. Compound 2 underwent a series of heterocyclization reactions to give the new pyrazole, isoxazole, cyclopentanothiophene, thiazole, triazole, 2H-chromene and pyridone derivatives (3-13). The elemental and spectral data (IR, 1 H NMR and MS) characterized their structures. Screening for some selected compounds was carried for their potential antioxidant activities using ABTS. Among the tested samples compounds 9, 11, 5 and 10 exhibited promising activity.

New heterocyclic compounds based upon rigid 3D-spiro chromanone scaffold have been synthesized and evaluated as efficient antimicrobial agents. Molecular docking and QSAR have explained and supported the observed promising antimicrobial activity.