用三氟甲磺酸二芳基碘𬭩盐和 N-碘代丁二酰亚胺由 N-对甲苯磺酰基-2-丙炔胺制备 3-碘喹啉。
Preparation of 3-Iodoquinolines from N-Tosyl-2-propynylamines with Diaryliodonium Triflate and N-Iodosuccinimide.
机构信息
Graduate School of Science and ‡Molecular Chirality Research Center, Chiba University , Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, Japan.
出版信息
J Org Chem. 2017 Nov 17;82(22):11727-11734. doi: 10.1021/acs.joc.7b01433. Epub 2017 Jul 26.
4-Aryl and 4-alkyl substituted 3-iodoquinolines could be smoothly obtained in one pot by treating N-tosyl-2-propynylamines with diaryliodonium triflate in the presence of KPO and a catalytic amount of CuCl at room temperature, followed by treatment with N-iodosuccinimide and BF·OEt at 0 °C, and then NaOH in methanol solution. The product, 3-iodo-4-phenylquinoline was smoothly transformed into 4-phenylquinoline with zinc; 4-phenyl-3-toluenesulfenylquinoline with toluenethiol, KCO, and CuI; 4-phenyl-3-phenylethynylquinoline with the Sonogashira coupling reaction; 4-phenyl-3-styrylquinoline with the Heck coupling reaction; 3,4-diphenylquinoline with the Suzuki-Miyaura coupling reaction; 2-cyclohexyl-3-iodo-4-phenylquinoline with cyclohexanecarboxylic acid, AgCO, and KSO; and 3-iodo-2-(2',5'-dioxan-1'-yl)-4-phenylquinoline with benzoyl peroxide in dioxane.
4-芳基和 4-烷基取代的 3-碘喹啉可以通过在室温下用二芳基碘鎓三氟甲磺酸酯处理 N-对甲苯磺酰基-2-丙炔胺，在 KPO 和催化量的 CuCl 存在下，然后用 N-碘代丁二酰亚胺和 BF·OEt 在 0°C 下处理，然后用甲醇溶液中的 NaOH 来一锅法顺利合成。产物 3-碘-4-苯基喹啉可以通过锌将其顺利转化为 4-苯基喹啉；用对甲苯硫酚、KCO 和 CuI 将 4-苯基-3-甲苯亚磺酰基喹啉转化为 4-苯基-3-苯乙炔基喹啉；通过 Sonogashira 偶联反应将 4-苯基-3-苯乙烯基喹啉转化为 4-苯基-3-苯乙烯基喹啉；通过 Heck 偶联反应将 4-苯基-3-苯乙烯基喹啉转化为 4-苯基-3-苯乙烯基喹啉；通过 Suzuki-Miyaura 偶联反应将 3,4-二苯基喹啉转化为 2-环己基-3-碘-4-苯基喹啉；用环己烷羧酸、AgCO 和 KSO 将 3-碘-2-(2',5'-二氧杂环戊烷-1'-基)-4-苯基喹啉转化为 3-碘-2-(2',5'-二氧杂环戊烷-1'-基)-4-苯基喹啉；用过氧化苯甲酰在二氧杂环己烷中转化为 3-碘-2-(2',5'-二氧杂环戊烷-1'-基)-4-苯基喹啉。
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