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. 2013 May 20;4(7):642–646. doi: 10.1021/ml4001084

Scheme 1. Syntheses of N-Alkyl-3-hydroxypyridin-4-ones, Their Gallium(III) Complexes and the Hybrids.

Scheme 1

Reagents and conditions: (i) BnCl, MeOH, 92 °C, 22 h; (ii) RNH2, pH 7 (10 M NaOH), 1:1 EtOH/H2O, 105 °C, 18 h; (iii) H2, Pd/C, 4 atm, 1:9 H2O/EtOH (aq), 4 h; (iv) Ga(NO3)3·9H2O, pH 8 (0.1 M NaOH), 80 °C, 4 h; (v) Me2SO4, (if pyranone R2 = Me) or MeI (if pyranone R2 = Et), 2.5 M KOH, acetone, rt, 12 h; (vi) neat, N2, 80 °C 1 h, then 130 °C, 3 h; (vii) 50% aq EtOH, pH 13 (2 M NaOH), 90–120 °C, 18–24 h; (viii) H2, Pd/C, 2 M ethanolic HCl, 4 atm or 1:2:3 H2O/EtOH/HCl, 74 °C, 24 h (Note: compd structural details can be found in Table 1).