Preparation of 3-Iodoquinolines from N-Tosyl-2-propynylamines with Diaryliodonium Triflate and N-Iodosuccinimide
作者： Teppei Sasaki , Katsuhiko Moriyama , Hideo Togo
关键词:
摘要: 4-Aryl and 4-alkyl substituted 3-iodoquinolines could be smoothly obtained in one pot by treating N-tosyl-2-propynylamines with diaryliodonium triflate the presence of K3PO4 a catalytic amount CuCl at room temperature, followed treatment N-iodosuccinimide BF3·OEt2 0 °C, then NaOH methanol solution. The product, 3-iodo-4-phenylquinoline was transformed into 4-phenylquinoline zinc; 4-phenyl-3-toluenesulfenylquinoline toluenethiol, K2CO3, CuI; 4-phenyl-3-phenylethynylquinoline Sonogashira coupling reaction; 4-phenyl-3-styrylquinoline Heck 3,4-diphenylquinoline Suzuki–Miyaura 2-cyclohexyl-3-iodo-4-phenylquinoline cyclohexanecarboxylic acid, Ag2CO3, K2S2O8; 3-iodo-2-(2′,5′-dioxan-1′-yl)-4-phenylquinoline benzoyl peroxide dioxane.
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