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. 2010 Apr 6;1(4):165–169. doi: 10.1021/ml100013s

Scheme 4. Synthesis of Benzoxaboroles with 6-OH and 6-NH2 Derived and Reversed Amide Linkage Groups.

Scheme 4

Reagents and conditions: (a) Ethylene glycol, TsOH, toluene, reflux. (b) BnOH, NaH, DMF, 0−65 °C. (c) n-BuLi, B(iPrO)3, −78 °C to room temperature. (d) HCl. (e) NaBH4, THF, 0 °C. (f) Pd/C, H2, MeOH. (g) PhNCO, Et3N, DMF, 0 °C to room temperature. (h) PhCOCl, NaHCO3, CH3CN. (i) BnBr, NaHCO3, DMF, 100 °C. (j) PhSO2Cl, K2CO3, CH3CN. (k) K2CO3, DMF. (l) Bis(pinacol-diboron), PdCl2(dppf)2, KOAc, dioxane. (m) NaBH4, MeOH. (n) Aqueous HCl. (o) Pd/C, HCO2NH4. (p) PhCOCl, Et3N, CH2Cl2. (q) AgNO3, NaOH, H2O, 0 °C. (r) Analine, EDCI, DCM, room temperature, 60 h.