Scheme 5. Synthesis of Thiazolidine-2,4-dione and Oxazolidine-2,4-dione derivatives.
Reagents and Reaction conditions: (a) (i) n-BuLi, THF, –78 °C, 10 min (ii) benzyl bromide, –78 °C to r.t, 1.5 h, (53%); (b) (i) t-BuOK, diethyl carbonate, MeOH, 70 °C, 19 h, then r.t., 24 h; (ii) n-BuLi, THF, –78 to 0 °C, 30 min; (iii) benzyl bromide, –78 °C to r.t., 2 h, (5%).