Fig. 1
From: Anti-malarial effect of novel chloroquine derivatives as agents for the treatment of malaria
Synthesis of SKM13 and SKM14. Reaction conditions: i l-phenylalanine, phenol, 140 °C, 1 h, 55%. ii N,O-dimethylhydroxylamine·HCl, EDAC·HCl, DMAP, TEA, DCM, rt, overnight, 72%. iii DIBAL, −40 °C, DCM, 5 h, 95%. iv phosphonate, DCM, KtOBu, 0 °C; (a) for SKM13 (71%), diethyl (2-((2-(dimethylamino)ethyl)(methyl)amino)-2-oxoethyl)phosphonate; (b) for SKM14 (70%), diethyl (2-((3-(dimethylamino)propyl)amino)-2-oxoethyl)phosphonate