Syntheses and biological evaluation of 2-amino-3-acyl-tetrahydrobenzothiophene derivatives; antibacterial agents with antivirulence activity - PubMed (original) (raw)

Scheme 1

Synthesis of 2-amino-3-acyl-tetrahydrobenzothiophene derivatives. Reagents and conditions: (a) S8, amine base, alcohol or DMF, rt, 24 h; (b) S8, morpholine, basic Al2O3, MWI, 160 W, 20 min; (c) acid anhydride, CH2Cl2, N2 gas, reflux, overnight; (d) NH3, MeOH, MWI 110 °C, 1 h; (e) NaOH, H2O, MeOH/THF, 80 °C, 6 h; (f) acetyl chloride, pyridine, rt, 2 h; (g) _tert_-butyl 2-chloro-2-oxoacetate, TEA, CH2Cl2, 0 °C, 5 min, then TFA, CH2Cl2, rt, 21 h; (h) p-Toluenesulfonyl isocyanate, TEA, toluene, reflux, 20 h; (i) Boc2O, DMAP, dioxane, 80 °C, 3 h, then N2H4, 40 °C, 1.5 h; (j) amine, TBTU, TEA, EtOAc, rt, 3 h; (k) TFA, CH2Cl2, rt, 1 h. * Yields of isolated products.