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. 2022 Oct 28;15(11):1335. doi: 10.3390/ph15111335

Scheme 5.

Scheme 5

Reagents and conditions: (a) suitable (R-CO2)O, anhydrous C6H5N, closed tube, 140 °C, 5 h; (b) 2/3-cyanophenylboronic acid (for 30a,b) or 4-ethoxycarbonylphenylboronic acid (for 33), Cu(Ac)2, Et3N, dry CH2Cl2, r.t., 12 h; (c) H2SO4 80%, 80 °C, 4 h; (d) Lawesson’s reagent, anhydrous toluene, reflux, 10 h; (e) NaOH 6N, EtOH 96%, reflux, 1 h; (f) (i) SOCl2, Et3N (catalytic), reflux, 1 h; (ii) anhydrous THF, 1-acetylpiperazine, 0 °C then r.t., 1 h.