Thiosulfuric acid analog of quinine as a potential antimalarial agent

Stereoselective Domino Rearrangement peri-Annulation of Cinchona Alkaloid Derivatives with 8-Bromo-1-naphthyl Grignard

“…9 S -Chloro-9-deoxyquinine and other 9-deoxy-9-halogeno-alkaloids were obtained by the treatment of the corresponding Cinchona alkaloid with thionyl chloride (56–84% yield) as described in the literature. 21 THF was purified and dried by sequential distillation from LiAlH 4 and distillation from sodium/benzophenone, and toluene was dried by storing over sodium chunks. All other reagents were purchased from commercial suppliers (Merck/Sigma-Aldrich and Fluorochem) and used as received.…”

“…Cinchona alkaloids were purchased from Buchler (Braunschweig, Germany). 9 S -Chloro-9-deoxyquinine and other 9-deoxy-9-halogeno-alkaloids were obtained by the treatment of the corresponding Cinchona alkaloid with thionyl chloride (56–84% yield) as described in the literature . THF was purified and dried by sequential distillation from LiAlH 4 and distillation from sodium/benzophenone, and toluene was dried by storing over sodium chunks.…”