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A new series of spiro[[1,3]dithiolane-2,3′-indolines]-2′-one derivatives was synthesized using Michael addition reaction of spiro[[1,3]dithiolane-2,3′-indolin]-2′-one to various α,β-unsaturated esters as well as direct alkylation of this compound with alkyl dihalides. Michael reaction of spiro[[1,3]dithiolane-2,3′-indolin]-2′-one and α,β-unsaturated esters produced related Michael adduct in the presence of tetrabutylammonium bromide and base 1,4-diazabicyclo[2.2.2]octane in good to excellent yields at 80°C under solvent-free conditions. Also, direct alkylation of spiro[[1,3]dithiolane-2,3′-indolin]-2′-one by dihaloalkanes in the presence of base K2CO3 afforded the corresponding products in good yields under the same conditions.