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Regio-Complementary Preparation of 6- and 7-Fluoro-1,2,3,4-tetrahydroquinolines via the Cyclization of Catecholamines Followed by Deoxyfluorination
Heterocycles ( IF 0.8 ) Pub Date : 2021-02-25 , DOI: 10.3987/com-20-s(k)56
Shuji Akai , Kazuyuki Saito , Shohei Sato , Keita Takubo , Kazunori Furutsu , Ahmed A. B. Mohamed , Euis Maras Purwati , Takashi Ikawa , Wang Zhou

We herein report a regioselective preparation of 6- and 7-fluoro-1,2,3,4-tetrahydroquinolines by applying the deoxyfluorination strategy, developed by the authors. This method includes the cyclization of catecholamines bearing an N-protecting group to form 7-hydroxy-1-azaspiro[4.5]deca-6,9-dien-8-ones and 6,7-dihydroxy-1,2,3,4-tetrahydroquinolines followed by deoxyfluorination, in which the nature of the N-protecting group has a significant effect on both the cyclization and the regioselectivity of the deoxyfluorination reaction.

中文翻译:

通过邻苯二酚胺环化,然后进行脱氧氟化的区域互补制备6-和7-氟-1,2,3,4-四氢喹啉

我们在本文中报道了作者开发的通过应用脱氧氟化策略的6-和7-氟-1,2,3,4-四氢喹啉的区域选择性制备方法。该方法包括将带有N保护基的儿茶酚胺环化以形成7-羟基-1-azaspiro [4.5] deca-6,9-dien-8-ones和6,7-dihydroxy-1,2,3,4 -四氢喹啉,然后进行脱氧氟化,其中N-保护基的性质对脱氧氟化反应的环化和区域选择性都具有显着影响。
更新日期:2021-02-25
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