Scheme 2.
Syntheses of 5-phenylthiazolesa
a Reagents and conditions: (a) methyl dichloroacetate, Na, MeOH, 0°C; then ethanethioamide, THF, reflux, 43%. (b) LiOH, MeOH. (c) Amine, EDCI, DMAP, CH2Cl2, 63–70%. (d) BCl3, CH2Cl2, −78°C, 36–50%.
Syntheses of 5-phenylthiazolesa
a Reagents and conditions: (a) methyl dichloroacetate, Na, MeOH, 0°C; then ethanethioamide, THF, reflux, 43%. (b) LiOH, MeOH. (c) Amine, EDCI, DMAP, CH2Cl2, 63–70%. (d) BCl3, CH2Cl2, −78°C, 36–50%.