Scheme 1.
Reagents and conditions: (a) (i) NaNO2, 37% HCl, ethanol, water, 0 °C, 20 min; (ii) ethyl acetoacetate, sodium acetate, ethanol, water, 0 °C, 2 h; (b) ethyl cyanoacetate, ammonium acetate, acetic acid, 170 °C (microwave irradiation), 4 min; (c) S8, morpholine, ethanol, 150 °C (microwave irradiation), 15 min; (d) LiOH•H2O, tetrahydrofuran, water, rt, 16 h; (e) amine, BOP reagent, N,N-diisopropylethylamine, dimethylsulfoxide, rt, 4–16 h.